Reader Case Study: Questioning The Financial Future With A Partner In Debt

Olivia recently bought her first home in the DC metro area and she loves her neighborhood and bike commute to her job at a nearby university. However, her boyfriend was fired from his medical residency program last spring and she’s trying to help him figure out his next steps while weighing her own financial goals. Olivia has requested our help in sorting through the complications that have recently arisen in her life.

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Case Studies address financial and life dilemmas that readers of Frugalwoods send to me requesting advice. Then, we (that’d be me and YOU, dear reader) read through their situation and provide advice, encouragement, insight, and feedback in the comments section. For an example, check out last month’s case study. Case Studies are updated by participants (at the end of the post) several months after the Case is featured. Visit this page to find links to all updated Case Studies.

I probably don’t need to say the following because you folks are the kindest, most polite commenters on the internet, but, please note that Frugalwoods is a judgement-free zone where we endeavor to help one another, not to condemn.

And a disclaimer that I am not a trained financial professional and I encourage people not to make serious financial decisions based solely on what one person on the internet advises. I encourage everyone to do their own research to determine the best course of action for their finances.

With that I’ll let Olivia, this month’s Case Study subject, take it from here!

Olivia’s Story

Greetings Frugalwoods! I’m Olivia, I’m 31, my boyfriend Jacob is 36, and we live in the Washington, DC metro area with my cat. I work at one of the many colleges in the DC area doing program evaluation for outside-the-classroom experiences. Jacob was in a medical residency program, but was fired from in May 2019 and is currently unemployed (more on that in a moment). We met at a mutual friend’s birthday party a year and a half ago and have been together ever since that night. (Let me tell you – I snatched him up quick after he explained his beer choice by comparing unit prices!). I bought my first house in March 2019 and Jacob moved in two months ago (in October 2019). My parents and sister both live nearby and I really love my new neighborhood.

From a vacation Olivia and Jacob took to Maine

Jacob and I aren’t married or even engaged, so one reason I’m submitting this Case Study is to get feedback on our path forward together, particularly in terms of how it will affect my financial goals. This isn’t a Case Study about Jacob’s financial life and goals, but rather about how what he brings to the table might affect me if we get married. I’d like to know how I can improve my situation in preparation for the possibility of marriage, and also for the possibility that Jacob and I don’t stay together. There are a lot of unknowns right now and I’m trying to think about, and plan for, two completely different futures. I also have questions about going from living by yourself to living with a partner.

I was single for a very, very long time before meeting Jacob. He’s certainly not perfect by any means, but I think we balance each other out extremely well in terms of our strengths in a way that we are still learning to manage. I’m much less relaxed and much more stressed with him in my life, but I also laugh more and am more social, healthier, and happier. I do want to say that his firing brought us A LOT closer. It seems crazy now that I have a house to deal with as we consider how to cope with his firing, but back in the winter/early spring of 2019, I wasn’t in a place to plan my future around the assumption that Jacob and I would stay together long term. I bought my house because it was absolutely the right decision for me if Jacob wasn’t in the picture.

Olivia’s Career

I’ve been in my role for just under three years–and received a raise in September–but I’ve been with the same employer for about five years. While working at this university, I pursued a second Masters degree (for free!) in Applied Statistics. My first MA is in Higher Education.

While I am absolutely underpaid for my statistics skills compared to what I could make in a corporate setting, I am well paid for working at a university in a non-academic role. Plus, my retirement and time-off benefits are fabulous!

Day to day, I manage national surveys, interview students about their experiences at the university, mentor graduate students interested in research, and analyze data in an effort to better understand how emerging adults develop in college and how we can foster this growth with a more efficient use of funds. It’s a more than 40-hour per week job (easily 50 hours, sometimes more), but for the most part I like my coworkers, the variety, and the work.

Jacob’s Unemployment Situation

Jacob has ADHD and a processing deficiency, which in part led to him being fired in early May from his medical residency program. He received pay and benefits through the end of June, but since then has been living off savings. He appealed the decision and, the day before Thanksgiving, we received final notice that the appeal process is concluded. He’s still fired, but they gave him a few more months of credit so he can more easily transfer to a different residency program and not have to go back through the match process. This is good because it gives him a bit more control over where he ends up. He’s now in the process of asking faculty to convert their appeal Letters of Support to Letters of Recommendation and looking into transferring to another residency program.

From a trip Olivia took with her sister and future brother-in-law to visit her dad, who is living on a sailboat in the Caribbean

Jacob has a lot of medical school debt as well as debt from a master’s degree that helped him get into medical school. For both the MA and medical school, he took out loans to cover tuition and living expenses. Given that, he has about $290,000 in student loan debt. He’s in the National Health Service Corps (NHSC), which had been paying him $30k per year in residency for his student loans and would give him a larger lump sum after he has worked in a high need area for several years. Since his firing, he requested a leave of absence from the National Health Service Corps and they’ve granted him one through next summer. As long as he is able to transfer to another program before then, he won’t be in default on his NHSC agreement and won’t owe any backpay to them.

The worst case scenario for my financial life is that Jacob moves to another part of the country to finish his training. We’ve assumed in all of our conversations that, were this the case, I would not follow him and that we would do our best to make long distance work. Because of his commitment to NHSC, it’s possible that even after he finishes training he won’t be able to move back since he’ll have to find a job in an area that qualifies as “high need” per the NHSC’s standards. This prospect leaves me in a rough spot financially if I want our relationship to last. While it could all work out just fine, it could also mean selling my house soon after buying it.

After I’ve done so much to right my own financial ship, this is a scary place to be. Jacob and I started talking about him moving in because of his financial situation, but we also felt it was the right thing for our relationship given how we felt about each other. I’m not charging him rent while he’s unemployed, but he is covering all grocery shopping costs. We’ve talked about him getting a job during this time, but decided that managing his current situation and searching for a new residency program is a bigger priority for him than having a small source of income.

Olivia’s Hobbies

Right now my hobbies consist of getting my house set up and accomplishing some admittedly basic DIY improvement projects that always take longer than expected. Prior to moving here, I had a work study position at a yoga studio and did yoga at least twice a week. I don’t think I’ve been to a single yoga class since I bought my house, despite having the cheapest studio I’ve seen in the DC area within walking distance! Jacob spent most of his summer and fall working to tame the front and back yards. A previous owner installed a bike ramp that took up most of the back yard, and after weeks of swinging a pick-axe and a hammer, we converted the ramp into three small steps, giving us a much larger back yard. We also bought some plants at the farmer’s market and flowers from a local nursery. Next year, we hope to put in some raised beds and harvest more than the 10 tomatoes we grew this year, but we’ve enjoyed the process and learned a lot!

Olivia’s Longterm Goals

A trail within walking distance of Olivia’s house

I consider myself lightly in the early retirement category as far as my future goals. I’m not stressing or trying to save every penny to get there as soon as possible, but I’d really enjoy being able to get up every morning, do yoga, have a cup of coffee, tend the garden, actually finish a New Yorker, and enjoy some silence. Right now, it’s not uncommon for me to have coffee for breakfast and forget to eat lunch until 3pm (if at all) because I have so many meetings and so many people asking me so many questions that I’m the only person in my department with the skill set to answer.

I’d like to complete a yoga teacher training program one day and maybe take an extended vacation (over a month) somewhere. I’d also like to get my PhD because I love learning and doing research. A big enticement for pursuing a PhD is that, in my current  job, I know a little about a lot of topics. A PhD program would allow me to delve deeply into one topic and finally feel like I’m an expert in something. I wouldn’t accrue any debt for a PhD because in my field, an assistantship that pays tuition and a stipend is common. I envision two potential scenarios for getting my PhD: I could be a part-time student and continue working in my current job (in which case my employer would pay), or, I could be a full-time student and take a pay cut by working part-time.

I’m interested in all of the following PhD programs: Higher Education, Student Affairs, Evaluation/Statistics, Information Studies, Survey Methodology, Education Policy, Education Leadership…. and probably some others. Right now, I’m leaning towards Information Studies and Education Policy, but that’s assuming I stay in my current role and attend a program part-time.  If I waited a few years until Jacob is working full-time on a physician’s salary, I might be leaning towards a different type of program assuming we spent a couple years dealing with his loans and were in a good enough financial position to drop my salary down to the $30k range that PhD students typically make for assistantships. Having already done a MA program part-time funded by my employer, I know that I can complete a program while working full-time but I also know that I would treat it more as something to “get through” rather than “learn from,” and I’m not sure I want to “get through” the PhD. I’d rather learn as much as possible.

Looking To The Future

In thinking about my future, if Jacob and I don’t get married, I see myself in this house and at this job for a long time. If we do get married, most of that goes up in the air as he’d like to live closer to his family in Vermont. Plus, some of the other goals he has would require us compromising. The biggest is that his parents parents are part of an LLC–with some family friends–and they jointly own a vacation property in the Northeast.

Ideally, I think Jacob would like to purchase partial ownership as he has strong emotional ties to the property. However, this would likely require a significant amount of money. There are several other differences between us that we’d need to resolve, such as how we might raise children and fund their education, but we are at the early stages of discussing these topics and figuring out where we stand. One of our biggest strengths as a couple is our open communication and honesty, so I’m not particularly worried. It’s possible that once he starts making a physician’s salary and paying back his loans in earnest, he’ll reevaluate some of his current habits and goals like the vacation property, but time will tell

Jacob and I both want kids and, given our ages, this is a priority for both of us to start talking about seriously and soon. However, it also seems impractical to have kids before Jacob’s residency is over; plus, I would personally like to be below $100,000 on his debt before having kids, which feels like a distant goal at this point.

Olivia Loves Where She Lives

My house is in an amazing community in the DC metro area. It’s a planned cooperative where the streets are organized around a central retail area with lots of walking paths and tunnels under the road. In about 5 minutes, we can walk to the grocery store, the library, the community gym and pool, a yoga studio, a couple restaurants – one of which has a different music performance every day – and the farmer’s market.

Olivia went to Montana for her 30th birthday with two of her closest friends

Plus, when we’re inside the house looking out the windows, we pretty much only see trees! My biggest complaint about the house so far is that the birds wake me up too early in the summer! We feel so lucky to be where we are.

Additionally, moving here has enabled me to bike to work most days of the week, which is the most consistent cardio I’ve ever done in my adult life. We also have some friends in the community – just the other night we walked to a friend’s house to play board games and drink wine. Driving, we’re about 20 minutes from my parents and about 40 minutes from my sister who is about to get married and wants to have kids soon. The house is a two-bed, one-bath with very little storage. I had a whole room dedicated to yoga before Jacob moved in, but that room is mostly storage now. I have a list of house projects I’d like to do, but these are on hold for the foreseeable future. All in all, I feel like I’m in a great house in a wonderful location.

Olivia’s House

The upside is that I bought a house by myself at age 31; the downside is that I did not put 20% down. I was in a situation where I needed to find new housing and knew that I could not live with roommates anymore. In DC, this is pretty cost prohibitive. I loved the neighborhood I lived in previously, but renting there would have been close to $2k/month and my commute was an hour. I found my current neighborhood based on thinking about my life if Jacob and I didn’t work out.

Given that, I pay the mortgage by myself, I don’t need a car here, there are affordable daycares nearby, and the elementary and high schools are both within walking distance. I’ve decided that I will have a child by myself (eventually) if Jacob and I break up. Being a somewhat single woman with aspirations of having a child (potentially while single), the idea of living in a cooperative where most routine maintenance is taken care of was extremely enticing.

Here’s the rundown of the house’s value and what I paid:

  • Appraisal Value: $179,000
  • Sold at: $178,000
  • Original Loan Amount: $160,200
  • Current Loan Balance: $156,387
  • Equity: $22,613

A downside of this house is that it does not have A/C, but I submitted the paperwork to have a mini-split system installed and we’re tentatively scheduled for install in mid January! This will have the added bonus of reducing my winter heating bill as I have electric baseboard heaters, which can be costly. I anticipate the mini-split will increase the house value quite a bit, which would help in getting to 20% equity. I currently pay extra on the mortgage every month to help facilitate this.

While it looks like I have the cash to drop on the mortgage to get to 20%, I wanted to instead pay to have the mini-split installed in 2020 since it’s part of a renovation program managed by my housing cooperative. I could technically not go through the cooperative for the mini-split installation, but that would involve finding contractors, getting board approval, and managing the process myself.  It was important enough to me to get these renovations done (mini-split system installed, through wall a/c removed) without the added back and forth with the board for approval and finding a contractor to manage the renovations. Further, I appreciate the clear cost estimate that the cooperative renovation program provides as opposed to an individual contractor, which lore tells me will often goes over budget.

Here are the costs for all updates occurring as part of the mini-split installation:

  • Mini-split installation: $7,260.00
  • Close through-wall hole for current window unit A/C & patch to match interior/exterior: $611.60
  • Install bathroom exhaust fan: $820.60 (required for rebate)
  • Co-operative processing fee: $150.00
    Total: $8,842.20
  • Pepco rebate (air flow improvements from updates done by previous owner): $150.00
  • Pepco rebate for mini-split install: $2,500.00
    Total after rebate: $6,192.20

Olivia’s Spending

My expenses have really gone up over the past year or so. I attribute this to several things: 1) there were some basic house startup costs and I’ll admit not all of these fell into the “need” category, 2) general “dating someone less frugal than me” reasons although it could be much worse, and 3) the stress of dealing with Jacob’s employment situation. In all honesty, #3 is what’s making it hard to tackle #1 and #2.

The beach at the Chesapeake Bay Foundation where I travelled with a group of 12 college students while they did service over spring break

There are days where I put in 10 or 11 hours at the office and then come home and spend the evening reading emails from Jacob’s lawyer and looking over documents. I’m happy to do this and I’m good at it, but it means that I don’t think about what I’m eating for lunch the next day and by the time the weekend rolls around I’m so burnt out I can’t bring myself to spend Sunday meal prepping, which then starts the cycle of spending all over again…

We’ve certainly improved over the months in this area as the shock and immediacy of the crisis has worn off and become a part of our day-to-day life. I’ve also resigned myself to making sure we have more things like mac and cheese and ramen noodles on hand.

As you’ll see below, by design I’m basically breaking even (or going into the red) every month, due largely to house start-up costs. I’ve received a few gifts of money from family that I’ve been using to cover the difference between my income and expenses My mom gifted me $1,000 to congratulate me on buying my house. Additionally, a family member recently passed away and left me $2,000. I’ve put these gifts into my emergency fund account and use that to cover any shortfalls each month. I will also use my emergency fund to pay for the mini-split installation and then will readjust the amount I keep in that account.

Olivia’s Credit Card Strategy

I love to travel and so I pay for almost everything with my Capital One® Venture® Rewards Credit Card, which earns me points for free airfare (this is an affiliate link). I have another credit card that only has my monthly Netflix payment set up to automatically pay each month. I keep that card because I’ve had it since I was about 17 and I’m pretty sure my excellent credit score is due in part to the length of time I’ve had this card.

Olivia’s Spending Strategy

Given that I’m in the fortunate situation of being able to put money towards both a 403(b) and a 457 retirement account, my goal each month is to have my monthly take-home pay stay as close as possible to my monthly spending. I think my emergency fund is healthy and my current strategy (which is up for debate!) is to maximize my pre-tax retirement contributions. If I needed to dip into my emergency fund for something, I would drop my 403(b) contributions until the emergency fund returned to a satisfactory level, but I would never touch my 457 contributions.

If I ever have “too much” money in my checking or savings account, I’ll sweep some into my Roth IRA. Now that I’ve bought the house, that extra money might not go towards the Roth IRA but perhaps something towards more exciting (dishwasher, anyone?). My thought is that this is preferable to lower regular pre-tax contributions to retirement and ending up with a surplus of cash that I can’t go back and put in a pre-tax account. This means I’m rarely saving cash while I have fairly healthy retirement accounts. I’ve never been completely confident that this is the best plan, but it’s the strategy I’ve been following for the past few years.

Olivia’s Finances


Item Amount Notes
Olivia’s Income $2,753.03 Olivia’s net salary minus health insurance, 403b and 457 contributions, and taxes.
Monthly subtotal: $2,753.03
Annual total: $33,036.36


Item Amount Notes
Mortgage and PMI $837 Interest rate of 4.38%
Co-op fee $654 Includes property taxes, some house maintenance and improvements, and common area maintenance.
Home & Yard $400 This is what I spent in September, which was mostly house start-up costs (3 bags of cement, a couch cover for a free couch, stringers for porch stairs we are DIYing, plants). I’m winding down in this area with the procurement of a fire pit from Freecycle!

For the past month, the only charge I’d classify in this area was a Christmas tree from the local Fire Department. Other than that, this category is now down to $0.

Extra Mortgage Payment $163 I did not put 20% down on my house, so I pay a little extra each month to help reach this goal sooner.
Travel $150 Included a visit to the Virgin Islands to visit my dad who is living on a sailboat! And a trip to Bangkok and Perth (thanks to my Capital One® Venture® Rewards points, my flight to Bangkok was totally free!).

This is the monthly average of October 2018 to September 2019.

Utilities: Electric $137 I have a single A/C window unit for the entire house and ran it a fair amount our first summer. I don’t have winter data yet, so this is the October 2018-September 2019 utility average including what I paid at my previous house (higher than the average since I moved).

I hope this’ll be lower once my mini-split is installed in mid-January 2020.

Eating out $137 I know this is ridiculous. Since meeting Jacob, this has increased both because he’s not as frugal as I am and because of the Crazy Life Events that have limited my time to meal plan and prep, resulting in more food purchased at work than I am comfortable with.

This is the monthly average of October 2018 to September 2019.

Car insurance $87 Through Erie
Cat! $55 This is the monthly average of October 2018 to September 2019.
Alcohol & Bars $51 I’m usually pretty good at separating alcohol from the general eating out budget.

This is the monthly average of October 2018 to September 2019.

Utilities: Water $46 This might include an overnight or two with the hose leaking + two leaky faucets (one we have replaced and we have plans to do the next one).
Clothing and accessories $42 Includes two pairs of black pants from the Loft for work that I had been searching for for years. I wore these pants every day to work this week!

This is the monthly average of October 2018 to September 2019.

Cell Phone (service for one phone) $37 Through Ting. In reviewing the past couple bills, it looks like I’m “medium” on almost everything, yielding $30 of usage before taxes.

I keep data turned off for all apps most of the time, but there are a few things that have increased my usage: being a car owner, my raise at work comes with the feeling that I need to be available all the time, plus one of my closest co-workers has an Android, which means all of their texts come in as SMS as opposed to iMessage (I have my mom’s old iPhone).

Internet $35 Intro rate for Comcast; internet only
Charitable Donations $30
Gas for the car $19 I don’t drive for my daily commute, which keeps this super low. This is the monthly average of October 2018 to September 2019.
Home insurance $16 Through Erie
Gifts $15 For birthdays, weddings, etc. This is the monthly average of October 2018 to September 2019.
Entertainment $14 This is the monthly average of October 2018 to September 2019. Includes cover fee to see a friend’s graduation from Improv school and axe throwing for a co-workers birthday.

**I will note that this increased dramatically in October 2019 because Jacob wanted to go to Six Flags for his birthday – wooooweee talk about expensive!**

Haircuts $11 This is the monthly average of October 2018 to September 2019.
Netflix $9 Gilmore Girls!
Groceries and household supplies $0 While Jacob is unemployed, he’s covering all groceries as his “rent” – we’d split the mortgage and co-op fee if he were to get a job in the area.

This usually includes household supplies as well although we haven’t really figured out what we’re doing in this area for the long term.

Monthly subtotal: $2,945 My goal is for my take-home pay to match my expenses. I don’t actually go into the red; rather, I invest a lot of my paycheck in my pre-tax retirement accounts.
Annual total: $35,340


Account Amount Notes Interest/type of securities held Name of bank/brokerage
457 retirement account $48,185 I contribute the max to this. 81% VINIX; 19%VBTIX TIAA
403b retirement account $35,609 With my raise in September, I now contribute about $650 per month here. Before I learned the beauty of the 457, I was putting money here and not in the 457. 78% VINIX; 22% VMCPX TIAA
403b retirement account $29,051 This is where my employer contributions go. My employer contributes 7.25% annually – not a match, just free. 65% VINIX; 30% VMPCX; 5% VBTIX TIAA
Money Market Savings Account $23,821 This is my emergency fund ($15,000) plus money for home renovations organized by the co-op community.

I will pay for the $6,192.20 installation of my mini-split from this account.

Cash; 0.85% annual percentage yield Navy Federal Credit Union
Roth IRA retirement account $15,043 I’ve had this for a long time, but this is the first year I’ll max my contribution. All in VTSAX Vanguard
Checking Account $3,528 I’ve been carrying extra cash here as I adjust to the costs of homeownership, but I don’t think I need this much in here. Cash Navy Federal Credit Union
Total: $155,237


Item Outstanding Loan Balance Interest Rate and Loan Terms Notes
Mortgage on primary residence $156,387 4.375%; 30-year fixed-rate mortgage Because I live in a housing cooperative, I technically bought a membership in the cooperative that comes with the right to occupy and make changes to my unit.

This also means that there were only 6 board approved lenders I could choose from, which means it’s a slightly higher interest rate than had I gone with something more conventional.

Total: $156,387

Debts: $0


Vehicle make, model, year Valued at Mileage
Toyota Corolla 2005 $1,500 182,000
Total: $1,500 Fully paid off

Where Olivia Wants To Be in Ten Years


  • In 10 years, I’d like to be close to financial independence. Since I’m intentionally taking the slower path, I know this goal will take longer to reach than 10 years, but I’d like to be on track.
  • While I want to be financially independent at some point, I like my job and am not in a rush.
  • Ideally, I’d like financial independence to happen whether or not Jacob and I stay together. Jacob is not interested in early retirement.
  • If Jacob and I get married, I’d want us to be debt free in 10 years.


  • I want to live in a walkable neighborhood (such as where I am right now!), go to yoga maybe five days a week, and spend lots of time cooking and reading.
  • I want to have kids, either with or without Jacob.
  • I want to reach a point in my job where I don’t wake up every day at 5:00am due to stress and start working.


  • I envision I’ll most likely be in my current position or one extremely similar (in terms of work and organizational hierarchy).
  • If I’m not, I’ll probably be in a full-time PhD program or doing something like AmeriCorps, which would cover basic living costs while I let my investments grow and transition to early retirement.

Olivia’s Questions For You

1) Regarding my house:

  • To what extent should I prioritize getting to 20% equity in the house given my current situation? I know I need to do this ASAP, but given the uncertainty about Jacob’s employment situation, I’m wobbling.
  • When you add up all my retirement contributions, I’m contributing over $38,000 per year. I know Frugalwoods generally doesn’t advise decreasing retirement contributions in order to save for a down payment, but at this level, I can’t help but wonder if I should drop some of my retirement contributions until I reach 20%? And if so, from which account?
  • Since I have to pay for the house to be appraised in order to have PMI removed, I am assuming that I should not count on the mini-split or other changes to impact my LTV at all. I should only ask for PMI to be removed once I have hit a solid 20% based on the original loan and appraisal, right?

2) Regarding my partner:

  • What suggestions do you have for supporting an unemployed partner?
  • I’m confident for now about my decision to not charge Jacob rent, but what do you think?
  • How do you cope with the uncertainly around moving in the direction of sharing your life with someone, but not being there yet? I see his huge scary debt cloud coming towards me, but we’re not at the point where I can do anything about it, and all the while, the debt just keeps growing…
  • If I marry Jacob, would I have to give up on my early retirement goal? This is the biggest question weighing on me right now. I’m not working towards early retirement at a rapid pace, but I also don’t want to give up that dream entirely.

Mrs. Frugalwoods’ Recommendations

Olivia is doing a fantastic job!!! At 31, she’s debt-free, owns her own home, and has retirement savings that would make most 50-year-olds jealous. I’m deeply impressed with the hard work Olivia put in to get herself in such excellent financial shape. She should feel proud of what she has accomplished and take a moment to revel in the good decisions she’s made over the years. I get the sense that Olivia might be a tad like me–always looking to the next goal and the next thing to achieve. While I 100% understand this impulse (and live with it daily… ) I encourage Olivia to take some time to reflect on the stunning financial accomplishments she’s made during her 20’s. Her twenties, people. Let’s reiterate that she is thirty-one. A mere babe and already in better financial shape that many people twice her age.

I want to start with Olivia’s second set of questions regarding her relationship with her boyfriend, Jacob.

Olivia’s Relationship With Jacob

Let’s start with some disclaimers:

  1. I am not a relationship expert (I’m not a financial expert either, but I play one on the internet).
  2. I don’t personally know Olivia or Jacob, I’ve never met them, and so I don’t have full insight into their relationship.
  3. I’m basing my opinions only on what Olivia wrote in this Case Study, which obviously doesn’t contain the full breadth of their relationship.

What jumped out at me over and over in Olivia’s Case Study were her concerns about Jacob and their potential future together. This is not to say that there aren’t wonderful and fulfilling aspects of their relationship, but those didn’t shine through in her write-up. I realize that this Case Study is just one small snippet of Olivia’s life, but here are some of the things she wrote about Jacob that gave me pause:

He’s certainly not perfect by any means, but I think we balance each other out extremely well in terms of our strengths in a way that we are still learning to manage. I’m much less relaxed and much more stressed with him in my life, but I also laugh more and am more social, healthier, and happier.

While Olivia noted she’s happier with Jacob in her life, she qualified it with quite a bit of negative, including the following:

After I’ve done so much to right my own financial ship, [Jacob’s debt]… is a scary place to be.

I also find it telling that while Olivia discusses some of the longterm financial considerations around a relationship with Jacob, she doesn’t describe a future with him in her longterm goals. Marrying Jacob, or being with Jacob, isn’t explicitly noted in her ten-year goals, although paying off his debt is. I know that Olivia is asking us about how Jacob would impact her finances–this is a personal finance Case Study after all–but she’s not asking it from a place of knowing that Jacob is who she wants to spend her life with.

I appreciate, and commend, Olivia’s circumspection around Jacob’s financial situation and I wish more people were this thoughtful before getting engaged. However, if you want to marry someone–and they are the person for you and you can’t imagine living your life without them at your side–you don’t care about their financial situation.

You should be informed about their finances, you should come up with plans and goals around their finances,you should actively work to get onto the same financial page, but their financial situation–be it good or bad–shouldn’t be a reason to marry, or not marry, someone.

Having a shared financial philosophy and shared life goals are–in my opinion–crucial to the longterm health of a relationship, but they’re not predicated upon both partners being in perfect financial shape at the outset (thank goodness or Mr. FW might not’ve married me… ).

I felt a pang of alarm when I read the following:

My expenses have really gone up over the past year or so. I attribute this to several things: 1) there were some basic house startup costs and I’ll admit not all of these fell into the “need” category, 2) general “dating someone less frugal than me” reasons although it could be much worse, and 3) the stress of dealing with Jacob’s employment situation. In all honesty, #3 is what’s making it hard to tackle #1 and #2. There are days where I put in 10 or 11 hours at the office and then come home and spend the evening reading emails from Jacob’s lawyer and looking over documents. I’m happy to do this and I’m good at it, but it means that I don’t think about what I’m eating for lunch the next day and by the time the weekend rolls around I’m so burnt out I can’t bring myself to spend Sunday meal prepping, which then starts the cycle of spending all over again…

Based solely on this, it appears that Jacob expects Olivia to be responsible for everything: to be the sole income earner for the household, to help him with his work, and to manage household chores such as cooking and meal prep.

They very well may have a more equitable division of labor ironed out, but the imbalance I perceive doesn’t sit well with me. Further, in all honesty, it doesn’t bode well for the potential addition of children and their attendant work and expense. If Olivia is giving up her free time to read Jacob’s legal documents, then in my admittedly uninformed opinion, he should do the meal prepping and pack her lunches for work.

My analysis doesn’t include any data about the emotional or romantic side of their relationship, but from the financial and household labor side of things, it seems a bit grim. I found it telling that Olivia noted the following: “I was single for a very, very long time before meeting Jacob.” I want to note that being single for a long time prior to a relationship does not mean that the relationship you’re in is the right relationship.

Additionally, Olivia included several mentions of having children on her own, which sounds like a concrete plan she’s thought through very carefully:

I’ve decided that I will have a child by myself (eventually) if Jacob and I break up. Being a somewhat single woman with aspirations of having a child (potentially while single), the idea of living in a cooperative where most routine maintenance is taken care of was extremely enticing.

I commend Olivia for identifying that motherhood is a goal for her and it seems she’s put herself in an excellent position to make that happen one day, if she so chooses.

I also want to acknowledge that this is a rough time for Jacob given his unemployment. And sticking with someone during a rough time isn’t easy. If Olivia wants to be with Jacob for the long term, they will figure out the finances. On the other hand, if she doesn’t want to be with him, but feels beholden to him because she’s supporting him financially, then she needs to prioritize her own needs and extract herself from the relationship. As she noted, they are not engaged or married and she is not responsible for him.

I’m concerned about Jacob’s financial impact on Olivia right now since she cited him as one cause of her increased spending. Further, he’s not paying rent, HOA fees, or utilities. Again, these are just my opinions and I am not in full possession of the facts. But since Olivia came to me for advice, I feel I’d be remiss if I didn’t share my concerns with her about her relationship with Jacob.

Let’s turn to her questions on PMI now.

Olivia asked: “To what extent should I prioritize getting to 20% equity in the house given my current situation?”

I’m not as concerned about Olivia’s PMI (Private Mortgage Insurance) as she is. Since her PMI is escrowed through her mortgage and since her mortgage payment is quite low ($837), I have to imagine the PMI isn’t costing her all that much every month. I don’t have a huge hatred of PMI. Sure, it’s additional debt tacked onto a mortgage, but sometimes it’s what you gotta do in order to buy the right house for the right price at the right time. Olivia is correct that it’s ideal not to have PMI, but it’s not the worst financial thing in the world. All that said, if reaching 20% equity and having PMI removed is a top goal for Olivia, she has the capacity to do it and she should go for it.

Wait, What’s PMI Again?

For anyone wondering what PMI is, let’s take a moment to discuss. Olivia did a superb job educating herself on home ownership, so this is the perfect opportunity to share her wisdom with the class.

For a definition, I turn to one of my favorite financial resources, the Consumer Financial Protection Bureau:

Private mortgage insurance, also called PMI, is a type of mortgage insurance you might be required to pay for if you have a conventional loan. Like other kinds of mortgage insurance, PMI protects the lender—not you—if you stop making payments on your loan. PMI is usually required when you have a conventional loan and make a down payment of less than 20 percent of the home’s purchase price.

Ok, does that make sense? PMI is an additional cost a mortgage lender will tack onto your mortgage if you don’t put down 20% of the home’s value at the time of purchase. Here’s some math to illustrate the point: If you want to buy a home that costs $200,000, you would need to pay $40,000 in cash as a downpayment in order to not have PMI added to your mortgage. I want to note that the rules are different for FHA loans.

Now, let’s talk about having PMI removed from your mortgage, again from the CFPB:

The federal Homeowners Protection Act (HPA) provides rights to remove Private Mortgage Insurance (PMI) under certain circumstances. You have the right to request that your servicer cancel PMI when you have reached the date when the principal balance of your mortgage is scheduled to fall to 80 percent of the original value of your home.

This is what Olivia is trying to speed up–the point at which she has 20% equity in her home. Olivia would eventually get to this point if she continued paying her monthly mortgage payment and didn’t pay any extra. However, she wants to pay extra every month in order to get to 20% faster in order to have the cost of PMI removed sooner. After PMI is removed, her monthly mortgage payment will be lower.

Let’s take a look at the numbers on Olivia’s house:

  • Appraisal Value: $179,000
  • Purchased For: $178,000
  • Original Loan Amount: $160,200
  • Current Loan Balance: $156,387
  • Current Equity: $22,613

20% of the original value of Olivia’s home ($178,000) equals $35,600 in equity. She’s currently at $22,613 in equity, which means she’s $12,987 away from her goal.

Let’s discuss how she might make this happen:

As Olivia noted,

When you add up all my retirement contributions, I’m contributing over $38,000 per year.

Between all of her retirement accounts, Olivia has $127,888 saved, which is phenomenal. I agree with her that she shouldn’t pause all of these contributions; however, I think it would be fine to redirect some of her monthly retirement savings.

  • Since the 457 is her most flexible and arguably best plan, I wouldn’t pause those contributions.
  • Since her 403b is pre-tax and the contributions are automatically coming out of her paycheck, I wouldn’t pause those contributions.
  • If she wants, she could pause her Roth IRA contributions because this account isn’t pre-tax and I assume she’s manually putting money in there every month, which would make it administratively the easiest to start and stop. The 2019 Roth IRA contribution limit for people under 50 is $6K and she said she’s maxing it out, so that = $500 per month.

If she took this $500 per month and added, let’s say, $750 in monthly savings (see my suggestions below), that’d be $1,250 per month she could funnel into her mortgage. At that rate, it would take her just over ten months to reach $35,600 in equity, which is pretty darn quick!

Furthermore, after she pays cash to have the mini-split installed next month, she could put some of her excess cash towards this goal. Between her savings and checking accounts, she has $27,349. Minus the $6,192.20 for the mini-split, Olivia could keep $17,670 in cash as a very healthy emergency fund and put the remaining $3,486.80 towards the PMI-removal goal. That’d knock her timeline down to just over eight months.

All that being said, I’m still not super hot and bothered by her PMI and wouldn’t encourage her to limit all of her retirement contributions in order to have it removed.

Start Saving For a Short-term Goal and Transition to a Long-term Goal

One appealing way to think about paying off PMI is that–after it’s done–she could start putting this monthly savings into index funds or other non-retirement investments. Once you get in the habit of saving at a certain rate, you might as well continue that savings even after your short-term goal is met. This could be a clever way for Olivia to set herself up for a very secure financial future. She would begin saving more with the short-term, easily achievable goal of having PMI removed and then continue that savings rate to fund investments that’ll facilitate her long-term goal of financial independence.

Olivia asked asked: “Since I have to pay for the house to be appraised in order to have PMI removed, I am assuming that I should not count on the mini-split or other changes to impact my LTV [loan-to-value ratio] at all. I should only ask for PMI to be removed once I have hit a solid 20% based on the original loan and appraisal, right?”

This is a tough one. While Olivia is correct that the mini-split will likely add value to her home, it’s impossible to say for certain if this would be reflected in the appraisal. The surest bet is to wait until she hits 20%.

A Review of Olivia’s Expenses

In every Case Study, I like to point out that what you choose to save or not save is a very personal decision. Cutting every last expense is NOT the right answer for everyone and I am NOT an advocate for making yourself miserable in the process of achieving financial stability. I am an advocate for values-based, goal-oriented spending. I think it’s important to assess whether all of your expenses bring you fulfillment and a good return on your investment.

In order to effectively review your expenses, you need to know what you’re spending. Luckily, there are software programs designed to do this for you. I use and recommend Personal Capital, which offers free expense tracking (affiliate link). You can write your expenses down in a notebook, you can create your own spending spreadsheets, you can use an online program–whatever you do, keep track of what you spend every month. If you’d like to know more about how Personal Capital works, check out my full review.

Savings Accounts Side Note

One of the easiest ways to optimize your money is to keep it in a high-interest savings account. With these accounts, interest works in YOUR favor (as opposed to the interest rates on debt, which work against you). Having money in a no (or low) interest savings account is a waste of resources because your money is sitting there doing nothing. Don’t let your money be lazy! Make it work for you! And now, enjoy some explanatory math:

  • Let’s say you have $5,000 in a savings account that earns 0% interest. In a year’s time, your $5,000 will still be… $5,000.
  • Let’s say you instead put that $5,000 into an American Express Personal Savings account that–as of this writing–earns 1.70% in interest. In one year, your $5,000 will have increased to $5,085.67. That means you earned $85.67 just by having your money in a high-interest account.

And you didn’t have to do anything! I’m a big fan of earning money while doing nothing. I mean, is anybody not a fan of that? Apparently so, because anyone who uses a low (or no) interest savings account is NOT making money while doing nothing. Don’t be that person. Be the person who earns money while sleeping. Rack up the interest and prosper. More about high-interest savings accounts, as well as the ones I recommend, here: The Best High Interest Rate Online Savings Accounts.

What impressed me most about Olivia’s expenses is that she provided us with yearly averages of her spending in each category. This is a phenomenal way to track expenses because it gives you the most realistic picture of what you spend each month. It’s not realistic to assume that what you spent in, say, November 2019 is what you’ll spend every single month of the year. While some expenses are fixed from month to month (such as rent/mortgage payments), most of us experience fluctuations in tons of other categories, such as: travel, dining out, groceries, healthcare, gifts, entertainment, pets, utilities…. you get the picture.

Where Olivia Could Save More

I don’t have much advice that Olivia hasn’t already identified in her “notes” section for each expense. She knows that reducing dining out and alcohol & bars would save her more each month, but she’s also hitting her savings targets at her current spending rate. If Olivia wants to seriously buckle down and wipe out her PMI ASAP, here are the discretionary areas where she could save:

Item Amount Mrs. FW’s Notes
Home & Yard $400 Olivia noted this category has reduced significantly in recent months, so this’ll be a big chunk of change she can put towards removing PMI.
Utilities: Electric $137 I bet this’ll be lower once the mini-split is installed. Yay!
Eating out $137 It’s totally up to Olivia whether or not she reduces spending in this area. She’s not in a crisis financial situation, so if she wants to continue eating out, she should!
Car insurance $87 This seems high to me, given the age of her car. I recommend shopping this around to see if she can get a lower rate.
Alcohol & Bars $51 It’s totally up to Olivia whether or not she reduces spending in this area. She’s not in a crisis financial situation, so if she wants to continue this expense, she should!
Cell Phone $37 I encourage Olivia to ask her employer to reimburse her cell phone bill. It sounds like she’s using her phone a lot for work, so I think there’s a case to be made here.
Monthly subtotal: $848
Annual total: $10,176

I’m not saying that Olivia needs–or even should–eliminate all of this spending (and obviously the car insurance and electricity aren’t going to go to zero). But, it is an illustration of where some of the PMI money could come from. One thought is for Olivia to do this bare bones budget for a month–or two–to rack up some extra cash to throw at her home equity.

Asset Allocation and Money Management 101

Below are the basic money management steps I advise just about everyone to follow. I’ve made notes of where Olivia is on each step and where she can focus more attention.

  1. Track your expenses religiously. Know exactly what you’re spending every month. If you’re not tracking your spending, you can sign-up for the free service Personal Capital, which is what I use and recommend for expense tracking (affiliate link).
    • Olivia is rocking this with her averaging of a year’s worth of spending in every category.
  2. Pay off high interest debt. List all of your debts in a spreadsheet and sort by interest rate. Prioritize paying them off in order of highest interest rate first.
    • Olivia is done with this!
  3. Build an emergency fund. An emergency fund should be kept in an easily-accessible bank account, such as a checking or savings account, NOT in investments, retirement funds, or cars/houses/expensive china. An emergency fund is money you can access immediately in an emergency. I recommend saving three to six months’ worth of expenses (meaning three to six months worth of what you spend every month, which is why it’s important to do #1: track your expenses).
    • Olivia currently spends $2,945/month, which means she should target an emergency fund in the range of $8,835 (three months of spending) to $17,670 (six months worth).
    • Between her savings and checking accounts, Olivia has $27,349, which she correctly noted is overkill. I like her plan to invest the remainder after she pays cash for her mini-split installation in mid-January. As noted above, she could also funnel some of this excess into reaching 20% in equity.
  4. Contribute to retirement accounts. Especially if your employer matches your contributions, putting money into a 401k or 403b is a no-brainer. Here’s more on why: 401ks Are Your Friend: Demystifying Personal Finance Part 3.
    • Olivia gets a gold star for contributing to not one, not two, but THREE retirement accounts. Her rationale for doing this is sound: she’s maximizing on pre-tax investments and limiting her take-home pay, which in turn reduces her tax burden. Smart.
  5. Start investing! Investing in the stock market is how you grow your wealth. Without this crucial step, you won’t reap the advantages of compounding interest and you’re unlikely to build your net worth in a meaningful way. I personally invest in low-fee total market index funds through the brokerage of Fidelity. Vanguard offers a similar product. You can do this yourself (it’s just like any other form of online banking) and there are more details here: For the Love of Frugal Hound, Manage Your Money Yourself! (by following The Simple Path to Wealth).
    • Since Olivia has such robust retirement savings, and since she’s interested in financial independence, I think it would make sense for her to consider opening a brokerage account and invest in something diversified and aggressive, such as low-fee index funds.
    • She should do her own research on what her risk tolerance is for investments, but I’d say it makes sense to have non-retirement investments. Even though her 457 doesn’t penalize early withdrawals, which is awesome, she won’t be able to access the money in her 403bs or Roth IRA until age 59.5 .
  6. Explore other options for investing in order to achieve diversification. After completing steps 1-5, you should continue investing (and rebalancing) on a regular basis (I recommend automating this process) and you can also start to look around for diversification options. This might include, for example, real estate. Mr. FW and I rent out our home in Cambridge, MA for a profit. Renting a property can be a fabulous financial decision and it can also be an absolutely abysmal one. It depends on many factors, including the rate of return you’d receive. For more on renting out properties, I recommend the site BiggerPockets, which discusses real estate investing.
  7. Analyze your income. Concurrent with all of this should be an analysis of your net income (that means the dollar amount you bring home every month, minus taxes and any other withholdings). In some cases, the best route to financial stability will be to increase your income while also lowering your expenses. Income is the crucial second piece to this equation and, the more you make, the more you can save. That’s a solid math fact.
  8. Create a credit card strategy. If you’re able to pay your credit card bills in full every month, using credit cards can be an excellent way to boost your credit score and earn rewards, such as cash back or hotel and airline points.

Closing Thoughts

It appears to me that Olivia has created a life she enjoys. She bought her own home in her ideal location, she lives close to her family, she likes her job (well enough, anyway), and she has robust personal and professional goals outlined, including pursuing her PhD, completing yoga teacher training, having children, and reaching financial independence. In all of her descriptions of her future plans, she mentions Jacob tangentially or as a barrier to achieving her goals.

While I’m all for sharing one’s life with a partner, I firmly believe you’ll be happiest if it’s the right partner. The right partner should build you up, encourage your dreams, provide moral support, be a team player in all aspects of your life together (household chores/childcare/finances/etc), and be someone you can’t imagine living without. I am not telling Olivia to break up with Jacob, but I am encouraging her to examine their relationship through the lens of what she really wants in her life.

I’ll recommend two books to Olivia that I haven’t read, but that have been recommended to me: Attached: The New Science of Adult Attachment and How It Can Help You Find – and Keep – Love and Marry Him: The Case for Settling for Mr. Good Enough. Both are research-based examinations of why people marry who they do, and how to find the right fit in your relationships.

Lastly, I want to address Olivia’s question about Jacob’s debt:

How do you cope with the uncertainly around moving in the direction of sharing your life with someone, but not being there yet? I see his huge scary debt cloud coming towards me, but we’re not at the point where I can do anything about it, and all the while, the debt just keeps growing.

In brief, you don’t. Olivia can’t–and shouldn’t–assume responsibility for Jacob’s debt right now. When and if they get engaged/married, they need to have a frank conversation about whether or not the debt becomes both of theirs. But right now? It’s not Olivia’s problem. While she can–and should–support Jacob emotionally through this job crisis, it’s not her crisis. Olivia did not choose to take out those loans and so Olivia is not responsible for paying them back. At least, not now and not until she and Jacob decide what’ll be best for their longterm financial future and ultimately, their happiness. I’m not a lawyer and so I can’t offer concrete advice here, but if Olivia does plan to marry Jacob, I encourage her to speak with a lawyer regarding her legal rights and responsibilities regarding his debt.


  1. Determine the importance of removing PMI. If it is goal #1, consider pausing some (but not all) retirement contributions, decreasing monthly spending, and potentially utilizing the excess cash in the savings account (after the mini-split is paid for).
  2. Consider opening a non-retirement brokerage account to invest in the stock market and diversify holdings to facilitate the goal of eventually reaching financial independence.
  3. Have a frank–and difficult–reckoning about whether or not you see yourself with Jacob for the longterm. Are you willing to give up on some of your personal and financial goals in order to be with him? Or, would you be happier pursuing the goals you’ve outlined potentially on your own?

Ok Frugalwoods nation, what advice would you give to Olivia? She and I will both reply to comments, so please feel free to ask any clarifying questions!

Would you like your own case study to appear here on Frugalwoods? Email me ( your brief story and we’ll talk.

User Generated Content Disclosure: reader comments and responses are not provided or commissioned by Frugalwoods or its advertisers. Responses have not been reviewed, approved or otherwise endorsed by advertisers. It is not the advertiser’s responsibility to ensure all posts and/or questions are answered.

Update From Olivia on 9/8/20:

Whew! Rereading that was hard. I don’t think I was in the best headspace for a Case Study when I submitted, to be honest.

I love Jacob, really and truly. No one has ever made me laugh so consistently, been so thoughtful and caring, and just in general a joy to be around. Just recently we were snuggling on the porch and he made me look up from my work to watch two hummingbirds in our neighbor’s yard – I would miss out on so much appreciation of the small things in life without him. We did sit down and read the Case Study together when it came out and had some hard conversations. He did do more around the house to help out, while also pointing out that what I was calling “not frugal” were things like buying Costco LaCroix (the idea of paying for a non-alcoholic or non-caffeinated beverage is just absurd to me), fresh salmon, and ice cream, but reminded me that he wears his clothes into the ground and refuses to spend money on new shoes, underwear, or socks (unlike me, who throws away socks and underwear once it has holes) or pretty much any other material good. We just each prioritize very different areas to be frugal in than the other person and we had a good, pointed conversation about that after the Case Study.

So, I don’t think my write up was a particularly fair picture of him or our relationship. I haven’t been in that grumpy, annoyed, stressed headspace really since COVID started. Honestly, I think I am just a HUGE introvert and the transition from living alone to living with an unemployed extrovert with ADHD while working in a highly social environment was incredibly draining. Working from home AND having Jacob go back to work has dramatically changed my mental wellness. Dramatically.

So, yes. Jacob and I are still together. After dealing with everything in his residency program* he got two offers to transfer to a new program (he had also started working at an Urgent Care clinic in the meantime). With COVID-19, I’ve been able to help him move, get him set up in the new program/city (which is GREAT and a dramatically better fit than his last program), make some freezer meals for him, while working remotely and having better work/life balance for myself too. I’ve recently returned home and will go back and forth as COVID and my work allow. We’ve been talking more and more about our future, getting on the same page about goals. The ADHD is still incredibly frustrating at times, but we’re working on it from a variety of angles — and working from home, as I mentioned, I have a lot more patience to deal with it.

A few updates on other things I mentioned in the write up:

  • The mini-split has been installed and it is GLORIOUS
  • My hyper focus on the PMI piece is probably a personality flaw – wanting to hyper-optimize everything but sometimes you need to just sit back and focus on living life
  • I stopped paying extra on the mortgage with COVID to save up more cash in case I am furloughed or worse, but still no word from my employer on what will happen

*With all due respect to everyone with strong opinions about his contract non-renewal, we talked with at least 3-5 Program Directors both in his specialty and others, some who knew him from med school and some who didn’t, and every single one of them believe that he should not have had to go through this. His letters of support/ recommendation were stellar, including comments such as, “the best resident I’ve worked with in my career.”

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377 Responses

  1. Wow, first off I agree with Mrs. FW that Olivia is kicking butt at her age. Being so young and motivated there’s no doubt she’ll achieve FI in her timeline, it’s just a matter of how she’ll get there.

    As a single person who is very comfortably financially independent and semi-retired, I can identify with Olivia’s struggle. It’s hard enough to find a compatible person in life but even harder when you desire the person to be at least moderately financially sound and responsible, since most American’s are not. I face the additional problem of wondering/fearing that the other person might find my wealth a part of the attraction, which is not something I want. I want someone who wants me for me, not for my net worth.

    So back to Olivia’s struggle with Jacob, I agree with most of what Mrs. FW wrote about the relationship, especially that Olivia should not assume any responsibility for Jacob’s debt and that she needs to do some deep self-reflection to figure out if he’s the right fit for he going forward. I don’t necessarily agree with the statement that “However, if you want to marry someone–and they are the person for you and you can’t imagine living your life without them at your side–you don’t care about their financial situation.” I want to agree with this statement, but for a frugal person aiming for FI I’m not sure it’s realistic. It’s kind of a cart/horse dynamic. In other worlds, I’m not sure how a frugal person aiming for FI like Olivia can even get to the point where they’re convinced “he’s the one” when they already know about the ‘less than frugal tendencies’ and the debt. Simply learning those things about another person will probably plant seeds of doubt, like it seems to have done with Olivia. Would Olivia be more ga-ga over Jacob if they never talked money and she didn’t know about his less than frugal tendencies? Perhaps.

    I agree with Mrs. FW’s statement that “Having a shared financial philosophy and shared life goals are–in my opinion–crucial to the long term health of a relationship,”. Absolutely. But I’m not so sure about “their financial situation–be it good or bad–shouldn’t be a reason to marry, or not marry, someone.” For “regular people maybe this is true, but for frugal and responsible people like Olivia we can see it’s planted enough stress and doubt that it’s a factor.

    Best of luck Olivia!

    • Mrs. Frugalwoods says:

      This is a great point, Dave. I wondered about that sentence myself when I wrote it and so I really appreciate your insights. I’m so far removed from dating (and Mr.FW and I were so young and broke when we got married… twelve years ago) that it’s hard for me to know what I would choose were I in your shoes (or Olivia’s). The breadth of reader experiences and the thoughtful, nuanced comments are one of the things I adore most about these Case Studies.

      • All I can say is the single life can be tough, and for folks like me and Olivia who are money-conscious and smart about finances it’s even tougher. Money problems are (I believe) the leading cause of divorce, so it’s a big deal.

        Great job on the case study!

        • Tonya says:

          I agree with this statement 100 percent! My frugality and my ex’s spending became a major issue that led to our amicable parting of ways. It’s a major life value and shouldn’t be ignored, especially considering a long-term relationship.

      • Rachel says:

        I totally agree that the important thing is having matching attitudes and habits. I was $100,000 in debt when I met my now-husband at age 21, and he had something like $150,000 at 25. But my debt was because my parents didn’t pay for any part of my college, and I was super thrifty and worked multiple jobs to avoid debt for more than tuition. His savings were because his parents paid for his college (inc. living expenses) and he lived in a cheap area post-college and invested all of his extra money because he didn’t know what else to do with it (which is awesome and we’re so glad he did, but it was basically out of apathy 😂).

        I paid off the debt in under two years by myself (I insisted) after I finished my PhD. Now we own a house together in DC and have a 60% savings rate. I earn significantly more than him but it didn’t matter to us then and it doesn’t now. The experience of being a self-funded student and paying off student loans as urgently as possible made me the much thriftier one, sometimes to my husband’s chagrin. So someone from the outside could have seen our starting net worths and made assumptions about us, but we very quickly equalized because we shared habits, goals, and priorities.

        • Caroline Bowman says:

          that’s just it; you shared priorities and neither of you had been fired at the age of 36 from a residency program. Your starting points financially were different and yes, clearly you are the more frugal, financially-savvy one, but it’s roughly even. You both worked together to get to where you both want to be, and it actually is quite inspiring that going from being so in debt you are now saving 60% of your income.

          I don’t see that here.

          • Rachel says:

            I totally agree, Caroline! Sorry if I didn’t summarize well. I think what I was trying to illustrate is that there are uneven situations because of life circumstances (uneven starting places, illnesses, maybe pursuing education or caring for family members) and then there are uneven partnerships because of lack of equal commitment or investment. I think Olivia deserves someone who will be her partner and work together with her toward their shared goals.

    • Georgia says:

      I think I agree with the ‘shouldn’t be a reason to marry or not marry someone’ because you don’t HAVE to take on someone else’s financial burdens when you marry…just like you don’t HAVE to take on someone else’s wealth when you marry! I have friends who signed a prenup, and they’re happy and have a kid and have even bought a house separately. Not my style, but there’s style out there for everyone! I know I would have married my husband in a second no matter what his debt situation was like, and for us everything is joint. Then again, I’m that kind of person—it all seems a bit like Monopoly to me sometimes. But it seems like it’s a huge source of stress for Olivia, and only she can really know how she wants to approach the situation….

    • Dorothy says:

      I agree with a Dave completely. In my experience, financial compatibility with a partner is as important, if not more important, than sexual or temperamental compatibility. We like to think we ”shouldn’t care about money”. But financial incompatibility can torpedo an otherwise-good relationship; it’s effect on a so-so relationship can be even more swift. One scenario I foresee — given Olivia’s description of their relationship — is that Olivia is pouring money that would otherwise support her own long-term goals — into a relationship that’s temporary. I feel a bit of wet-blanketing here, while it sounds mean, is realistic.

      I, too, share Mrs. F’s concern about the way Olivia talks about her partner and the description of the inequity in their arrangement. What, for instance, prevents Jacob from planning and prepping the meals as part of his contribution to the household? I get that his job stress is burdensome, but life goes on.

      Olivia description of Jacob’s family’s vacation home suggests they are people of means. Can they pitch in and help him so that the entire burden of financially subsidizing his living expenses doesn’t fall entirely upon Olivia?

    • Amanda says:

      I think that, when you’re younger, money management is something you can hopefully develop together. But those habits are pretty ingrained by the time you hit 30, plus you’ve had another decade or so for the effects to show. Does Jacob have any retirement savings? If not, that’s going to impact her FI plans.

      Money is such an important part of your life, that I absolutely do think you should factor it into your decision to marry someone. It’s not the only or the most important thing. But it does matter quite a bit.

      That said, “is not inherently frugal” doesn’t need to be a deal breaker. If someone is not inherently frugal, but is willing to talk openly about money, respects your decision to be frugal, and can control their spending to meet their own goals – that’s something a frugal person might be able to live with! The bigger red flag, to me, is when someone is unsupportive of your goal to be frugal, because that points to a larger incompatibility.

  2. Olivia says:

    Woowwwwee! Olivia here. Certainly some hard to hear things here about my relationship, but good things to consider. As I mentioned, Jacob and I have excellent communication so I see some hard conversations in our future. Although I will admit, I told a co-worker once that we had great communication and her response was “but does anything *change*?” – and that’s something that certainly needs to happen (that, again, we’ve talked about). I will say there are lots of excellent things about our relationship romantically that don’t come through, for sure. I think I’ve been trying to play to his strengths too, but his strengths are not the things I need (yard work) right now, and perhaps I need to be more firm on that.

    I think a lot of my submission of this Case Study was emotional – after being single for so long and being sad about it, I created a back up plan that I could be excited about. What I’ve been reflecting is the possibility of feelings of grief over possibly having found my person (life option #1!) which means this back up plan I created is no longer maybe my future. I am ok with that, but I’m still processing the emotions that were tied to that plan. I think Mrs. Frugalwoods point on how this division of labor would work out with kids is a good thing to reflect on. It’s was also interesting for Mrs. Frugalwoods to point out that I don’t include him in my 10 year plans and I need to do some more thinking on that. My gut reaction is that a partner is easily included in all of those goals and that those goals allow for flexibility to include Jacob’s goals, and that it’s hard to plan for that future with so much uncertainty and lack of location control over the next 2-5 years… but then I wonder if I am just being defensive and making excuses.

    Similar with PMI – I have just heard “avoid! avoid!” my whole life, and so I have been stressed about feeling like I did something wrong and need to fix it ASAP. It’s nice to hear that while I’m on the right track to addressing it, I don’t need to be as stressed as I seem to be (although I could make more progress).

    There’s so much more I want to write! But I’ll stop there for now. Looking forward to hearing your alls thoughts! Especially from those of you who might have insight on the emotionally supporting an unemployed partner topic. Clearly maybe I’m doing too much of that in some of the wrong ways and need to redirect.

    • Mrs. Frugalwoods says:

      Thank you so much, Olivia, for your open and receptive response! I can’t imagine how tough it is to read a stranger’s advice about the most intimate parts of your life and I applaud you for your insights and your willingness to examine these aspects of yourself. I am rooting for you!

    • My husband didn’t know how to boil water when we started living together. Cooking was not a strength. Now it is. The only way something becomes a strength is through practice.

      • Steve says:

        The big difference here is that we are talking about cooking vs. debt. If one can’t cook, then they can still eat. .If one is in serious debt, they could be a major burden.

    • Melissa says:

      Hi Olivia-
      I’ve been in your situation a few times, and I’ll tell you that you can’t change a man. While this is incredibly hard to hear, especially from a stranger on the internet, you did open yourself up for these concerns. And I have a feeling that you have been concerned about these things as well. If he was fired from his residency, that’s a huge red flag. Unless he does some serious internal work, including medication and therapy, these things will keep happening. He will continue to have a hard time with follow through, which is essential in a medical career. And if he washes out of medicine, he cannot have those student loans forgiven in bankruptcy.

      I think you need to give serious thought to not only is he a good fit emotionally, but can I continue to support him if he continues to have issues holding and keeping a job.

      Again, I know I don’t know you, and I don’t know him. I’m just giving my two cents as someone who has been there and left the situation penniless and having to start from scratch. Its a terrifying place to be, and one I don’t recommend. I hope you’ll consider getting some therapy for yourself to help you look at why you are with him, why you want to say, and how to manage this relationship without being his mother. Best of luck.

      • Olivia says:

        I agree completely about this being fired as a huge red flag. I’m a doctor (in the UK, so it might be a bit different), and for someone to be fired from a training programme is very rare and a major concern as to how he would cope in a training programme anywhere else (the work won’t be much different). If there are no specific circumstances that lead to this and the problems were entirely to do with his underlying difficulties, he needs to use the time he has now putting some serious spadework into therapy, medication – whatever will help. Alternatively, he needs to seriously consider if medicine is the career for him. I appreciate you didn’t ask for our opinion in his career situation, and I think you’re incredibly brave to be bringing this discussion here, but I do feel the need to point out that this is an uncommon thing to happen, and the way he analyses and deals with it is important. Best of luck to both of you!

      • I am a doctor in the US, on faculty at a medical school with a residency program in my specialty, and I absolutely cosign that dismissal from a training program is a HUGE red flag for any future program considering taking Jacob on. I’ve been on the faculty/chief resident side of quite a few struggling residents and only one was dismissed, and only after months of attempted remediation. It’s extremely rare. That sort of thing follows you through every licensure/privilege application, which may make it difficult for Jacob to get a job as a practicing physician, at least in a competitive area like DC.

        • Jen says:

          As another US physician, I completely agree. Being fired from a residency program is hard to do, is a big red flag, and completely different than being fired from another type of job. This will follow him everywhere, and makes his future in the medical field very uncertain, even if he is otherwise a great guy. And all of this is made much worse by his debt. Plus, right now, primary care would essentially be his only option with his medical training history given how competitive the other fields are. And unfortunately, primary care doesn’t pay a high enough salary to get all of that debt paid off. But the national health service corps is a huge asset for him in this situation!

          • Jen says:

            My sentence should have read “get all of that debt paid off quickly.” It is, of course, eventually possible! 🙂

    • Amanda says:

      Olivia – I could’ve written a lot of the same things about my relationship with my now-husband, who also got fired from him job while we were still dating because of issues with his ADHD. I know this isn’t a case study about your relationship, but if I could offer some unsolicited relationship advice, here’s what I’d say:
      – Is he implementing a concrete plan for learning to manage his ADHD? Has he reflected on what he did wrong that led to his firing, taken full responsibility for it, and made a clear plan to ensure that it doesn’t happen again? Is he actively working with a psychologist and/or psychiatrist to manage this issue? If yes, it may be that in several years he will be much better. If not, I would be very, very wary of your future together.
      (My husband has learned to manage his ADHD, but he’s also been occasionally resistant to working with professionals. We’ve reached a point where that is a necessity if our relationship if going to survive, so he has a psychiatrist and occasionally works with a therapist. Getting to that point took a LOT of stress, tears, fights, etc. I do not wish that on you)
      – Given that he’s unemployed and you’re working, is he basically doing all the housework? Because he should be, especially if you’re using your off hours to help him salvage his career. If he hasn’t voluntarily started to do all the cleaning, cooking, laundry, etc. needed to make a household run, but he’s letting you do those things on top of working 10 hours and dealing with his firing, I would be very concerned for your ability to have children together.
      – When you openly discuss problems, does he seek to find and implement solutions? Or does he want you to come up with solutions? The former shows that he’s trying, and you can definitely work with that. The latter suggests that you’re carrying the mental load in addition to the physical and financial load of this relationship, and that’s not okay.
      – If you break up, are you going to be okay with the fact that he was able to take advantage of free housing for the time in which he lived with you? Right now, he has a VERY good deal. I would not have let my unemployed boyfriend live with me for free – when my husband was unemployed, he still paid his part of the rent. Maybe you feel differently because you’d be paying for this house regardless, but you’re giving up space for him, and groceries isn’t the same as rent. So that’s just something I’d push you to rethink.

      Some of this probably sounds like tough love and I definitely don’t have all the details, but these are things I wish I had spent more time considering years ago. As it is, my husband and I are currently in marriage counseling to figure out if we can rework our marriage, and we’re working through a lot of the things I mentioned above, which we never fully addressed in the past.

      As for your 10 year plans, given that you’re unsure about this future of the relationship, I think it 100% makes sense that you’re not yet including him in your long-term plans. That said, if you move forward with the relationship, all of those plans are going to be up for discussion (as are all of his), until you land on some hybrid version of plans that you’re both happy with. That’s a really hard process, though, and I wouldn’t personally invest in it until you know that he is a stable, equal partner who you can rely on.

      If you do decide to go forward in this relationship, I can’t recommend couples counseling enough. Do it BEFORE you get legally married and talk about all the sticky issues – money, division of labor, gender roles, future plans, all of it. Best of luck, I hope that no matter what happens you land on something good.

      • Rachel says:

        Yes to all this! I have many family members with ADHD and it’s a struggle for everyone even in the best scenario, with full commitment to treatment.

        Also wanted to mention (from my previous area of research) that sharing of household labor tends to get more uneven 1) when a couple marries and 2) when a couple has kids. My husband and I are both deeply committed to being egalitarian but it’s still an ongoing challenge. If Olivia feels like her partner isn’t doing his fair share now, it might get even harder with marriage and children.

      • Laura says:

        Everything Amanda said here – all of this.

      • Sheila says:

        Hi Olivia, I agree with everything Amanda and Dave said. Also you are kicking so much ass, I commend you.

        You remind me a lot of myself, single throughout my 20s, bought my condo at age 30, met my boyfriend (now partner) later that year. My boyfriend was in a pinch because he got kicked out of his house due to the owner wanting to sell. He had a choice to live somewhere else on his own, but we made a choice for him to move in with me, and I charged him the same rent as if we were renting the apartment together. From the beginning it was always a choice for him to move in with me, and an advantage to the both of us to flourish our relationship together into a domestic partnership. He is about to take a 3 month unpaid sabbatical for his own mental health, but our financial contributions will remain the same. It might be helpful for you both of you to understand what it would be like for him had he not met you. What would he have done for himself while single? I sympathize with you being a supportive partner, but I think you need a tangible partnership in return (something other than the relationship perks). A philosophy that my partner and I share are that we are individuals for now (until we share a family and a house we purchase together) who support one another emotionally. We are solely responsible for getting ourselves into a career that pays our bills.

        I would also be wary of equating groceries for a household that is not in active-meal prepping mode as a fair share of household contributions for the two of you.

      • Annie says:

        This is spot-on.

        I’m sure you have a wonderful romantic connection and deep feelings for one another, but as you get older and especially once you have kids, the nitty-gritty matters so much more. He needs to be proactively working on these issues or else they will plague you forever. You deserve the very best.

      • Olivia says:

        This is so helpful! I greatly appreciate your insights into being in a partnership with someone with ADHD – this has been a huge learning curve for me and I imagine that some of my challenges probably come from not quite knowing where the line is on understanding the disability, working around the disability, and strongly requesting/forcing him to work through some of these issues for our greater benefit. You pinpointed exactly how I feel about the housing – I’d be paying for it regardless, but it does mean that my spare “yoga” room has now largely become storage. Checking in with him about what he’s learned from this experience with regards to his ADHD is also on the list – we’ve had some conversations about it but I haven’t dove in too deeply given how recent it still is. You raise excellent points about checking in with his ability to make sure he learns from this.

        All that being said – I’m also so sorry that you are in marriage counseling and I hope that you both are able to work through your challenges! It’s not easy, that’s for sure.

        • Amanda says:

          I’m glad that it was helpful and didn’t come across as overly harsh. The reality is that ADHD is something you can totally manage and live with – someone with ADHD may never process things in the way that someone without ADHD might, but they can learn habits and skills that allow them to flourish.

          But the thing is that HE has to work through it – you can’t do that for him. I’ll repeat that because it took me a long time to learn it: you can’t manage his ADHD for him. He needs to develop the skills and habits that allow him to flourish. And if it’s at the point where he’s getting fired because of it, he probably needs to work with a professional to do it, because he’s probably got some really negative ingrained habits and mindsets that he’s going to need to work through (with someone who isn’t you).

          I will say that, despite the frustrations, I love my husband. He supported me while I finished my PhD and always has my back. But as we’ve started taking on more “life responsibilities” (joint home ownership, talking about kids), the bouts of forgetfulness or inability to contribute fully to the household have become much bigger problems than they were before. That’s why we’re in counseling, and it’s been productive and really not a bad experience, but I really wish we’d worked through all of it sooner. So that’s my .02 for what it’s worth. I’m wishing you the best of luck!

        • Winifred Tigerlily says:

          Just to add … I married very young and impulsively in my early 20 (and was a divorced in my mid 20s) then spent about 23 years single. I met the love of my life 9 years ago (fixed up by his son, who was dating one of my employees) and we’ve been married 4 years now. I never had children or wanted to, so that’s different from your situation, but just wanted to add that I was in several unhappy relationships in my 20s, 30s and 40s that I “settled” for because I was afraid to be single.

          • Louise says:

            On the ADHD thing, my partner and I BOTH have it – and we also both have experience with other mental health conditions and with ex-partners with the same. The key thing we’ve both found with all of these things is the difference between acknowledging it and finding solutions and workarounds, and using it as an excuse. If there’s something that you’ve identified as an issue, have you found a solution that works and a way to make sure it happens? Or is it just a case of ‘oh, that’s my adhd and therefore not my fault’ (because that’s not ok!)? We all have certain disadvantages in life and it’s what we do with them that matters – actions, not words. An example – I’m really good with money and my partner (whose ADHD is worse than mine!) is TERRIBLE with it, plus it was a huge issue for me in a previous relationship. He works longer hours than me and earns more, but has higher bills and less saveable income than me (child maintenance etc from the first relationship). So, we found a solution that works for both of us. I carefully manage the budget for the household and he transfers me half of the bills etc and a large percentage of his money each month to save FOR him in a separate budget category (we realised that if there’s money in his account, he tends to think it’s spendable, so it lives in mine). This way he’s saving and not wasting money, I feel in control and trust him, and we can see really clearly where we are. We also keep a record of payments so neither of us feels taken advantage of. It took a few attempted systems to get to this, but the key thing is that we kept trying until it worked, because it was important for my wellbeing and so he kept trying.

            There also isn’t anything we don’t talk about. Anything that’s uncomfortable we sit down together and thrash through being totally honest. My ex wouldn’t do this and it was hugely stressful. Honesty is really important.

            The two youtube channels How to ADHD and Totally ADD are also really useful for learning about what’s adhd and what isn’t! 🙂

    • Rosalie says:

      As someone who was also single for almost all of my 20s (and also as a woman who knew early on that I wanted a kid and would have one/some on my own if I didn’t have a partner), I totally relate to having a 10+ year plan that doesn’t take for granted that you’d have a partner. I got together with my wife when I was 30, and a year in we hit an obstacle that I didn’t think we could get through, and even though the idea of losing her was kind of devastating I was somewhat comforted by knowing I had (sort of) a plan to do it all on my own. So, I don’t think it’s necessarily a red flag that you are making some mental plans that may not include him, since you can also say, if he was still in the picture some of this stuff would be easier to achieve, like kids. Making science babies is expensive (I can’t bring myself to tally up how much my wife and I spent on sperm and insemination but it’s over $10k), and daycare costs $1600+/month in my metro area which is similar or maybe a little cheaper than DC. Also, becoming parents has magnified my conflicts with my spouse, not diminished them. We don’t fight about money but we do have the same couple of fights over and over like I think everyone does, and having a kid (who at almost 3 still doesn’t sleep well) made us somewhat less patient with each other.

      Anyhoo, you are doing a truly great job and while I mostly kinda agree with Mrs. FW in her assessment of how you talk about your relationship here, you’re the one who knows yourself and your partner and what is workable. If you think change can happen, or if you can cope with the distribution of labor because soon J will be working insane hours and not available to help anyway, well, lots of people make that choice!

    • Caroline Bowman says:

      You deserve the very best Olivia, and if you genuinely love Jacob and you can see some real change (your colleague is spot-on, talk is great, but cheap!) emanating from him, and him taking initiative to improve your lives / his life situation would go a long way to ease the various doubts.

      No one is perfect, me least of all, but I’m in my 40’s, been married 15 years and of all my friends who are married / have been married / long-term partnered, the ones where one partner is essentially a child, nannied, lectured, run-around-after leads to sour resentment in time, even when the resentful partner has essentially created the ”monster” in various ways. Financial alignment is important. It’s boring, but important. You are clearly concerned already, and you should 100% listen to your gut very closely because so far, you have made some very, very prudent, wise decisions re your life goals.

      Also, you are 31, not 61. You may indeed have a child as a single person one day and you are very well-organised if you choose to do that, but equally, you could meet someone else. You are young and have so much exciting stuff ahead, with or without this particular relationship.

    • Shannon says:

      After being in a long term relationship with someone that did not share the workload, I have to say it was awful. If he’s home now, he should be doing all the cooking/cleaning/everything. I don’t believe that his job hunt is taking 50 hours a week.

      • Beatriz Cervantes says:

        My ex-husband was not financially responsible at all but I went along. When I remarried, I discovered how important it is to be in the same page and have the same (frugal) philosophy regarding how to use and save money. My husband and I are SO compatible and it makes our life and planning for our future a real joy.

    • Olivia says:

      I’m going to reply to my own comment so it sits a little higher up – I do want to clarify that while Jacob is less frugal than me, he’s more frugal than anyone else I know. I’m kicking myself to wording it the way I did. I’ve seen him buy clothes only once since we’ve been together and they were at a thrift store. There’s MANY clothes I think he should get rid of that he swears have more life in them. He wants to use old receipts as scrap paper and as I mentioned he did probably $2k of yard work without my asking, by himself, asking for lessons from a friend when he wasn’t sure what to do. He certainly enjoys La Croix and this is something I wouldn’t spend money on that he does. He rides an hour and 15 minutes on his bike to work currently (shadowing, not paid) each way and won’t get a new one despite it only working in one gear (after trying to have the bike shop repair it). He has two backpacks he uses for commuting, both of which have holes in them. I wanted to buy him a new backpack for his birthday, but he placed a higher value on roller coasters – thats what he wanted. I will admit that the division of labor needs to be addressed, but I think we are more well matched in our financial habits than any friend or boyfriend I’ve ever had in the past.

      • Janis says:

        I’m not trying to condemn or pass moral judgement here, but having a child without a father present is one of the ills of our society. Fatherless young men are one of the reasons that crime is rampant in many places. Fathers aren’t just “sperm donors” and are important to a child’s well being. However, if you don’t give birth as a single person to a child, why not adopt a child? It is a selfless and loving thing to do and helps society.

        • Amanda says:

          Janis – Kindly, I’ll say that your opinion does come across as judgmental, and it’s also not a very well-informed one. While there can be economic challenges to parenting as a single person, plenty of children from single-parent homes have wonderful childhoods and go on to be just as well-adjusted as children from two-parent homes. Blaming crime on single parents is just plain ignorant and wrong. Someone as thoughtful as Olivia is going to raise a wonderful child, regardless of whether she has a male partner or not.

        • Annie says:

          Janis, would you tell a married couple who are able to conceive to adopt rather than procreate because it is the selfless thing to do? Probably not. Being single or struggling with fertility doesn’t mean you carry the obligation to adopt a child.

        • Blair says:

          Just here to second what Amanda said. There are women, lots of them, who stay in miserable relationships because of the exact ideology you are perpetuating: that it’s better for women to be unhappy and for their children to grow up in a stressful home than for a woman to raise a child alone. We don’t need to be putting that guilt and shame on women, and we don’t need to be sending the message that any father and any relationship is better than not having one at all.

        • Caroline Bowman says:

          Janis, I think perhaps there’s been misunderstanding; Olivia wants to have a child, not help society as such. Adoption is certainly a way to become a parent with many, many examples of ways that’s worked very well.

          One question though, if it’s not okay for her to use a man as sperm donor to become a parent because society’s problems and high crime rates are a direct, immediate result of absent fathers rather than, say, systemic inequalities, high unemployment, terrible social care, then how is it okay to adopt a child with no father in the picture? Surely the same problem would apply. I’m confused. Where would be the father for this adopted child? Do they not also need one, possibly more, having presumably lost one already.

        • Luisa says:

          Janis, adoption is not something to take on lightly. If someone doesn’t want to adopt, they shouldn’t do so, no matter the benefits to the child and society. Period. Even if you desperately want to adopt, it’s not easy. It can be very, very expensive, and it can take years to come to fruition. My husband and I wanted to adopt–that was plan A for us–but we were deemed ineligible due to a health condition my husband has. My friend, who is infertile due to having breast cancer in her 20s, adopted a little girl with her husband. Given my friend’s health history, the only place they could adopt from was Vietnam, which is now closed to international adoption. My cousin and her husband were adopting from the foster care system, and they fostered a baby for 10 months. One month before their court date to make the adoption final, the birth mother changed her mind. Adoption is a beautiful way to create a family, but no one should “just adopt.”

      • Annie says:

        Olivia, that clarifies a lot regarding his frugality. You seem fairly aligned in that regard.

      • Caroline Bowman says:

        Well, clearly he is not lazy, which is a great thing, and kudos to him for doing so much for the garden. The thing with ADD is that there can be areas of hyper-focus that are sometimes very productive and other times… less so. Using an essentially broken bike for 2.5 hours of every day, when there simply must, must be low cost alternatives he could look to feels martyred and tunnel-vision in approach.

        However. As you have said, he isn’t a big spender and is clearly frugal by nature. He sounds like a lovely guy with many great qualities, and evidently he loves and cares for you, which is always a win. I just think he needs professional, longer term input into his issues than you could reasonably provide.

    • Allison says:

      Hello Olivia,

      I’ve have now read every comment and your responses to some of those comments…so I have a little advice.

      I am almost 43 years old, and like most women who have commented, have dealt with a partner who leaves a little to be desired…luckily, I figured it out but not before I lost 2 1/5 years….the signs were there all along but I chose to ignore them. The final sign for me was when I found out my (ex) boyfriend had $227k in student loan debt because he kept trying to “better” himself by getting advanced degrees when in reality, I think he kept going to school in order to not have to pay those loans back. It hit me that if I married this person, my life would be impacted by the paying back of these student loans and of course, all his other issues that would then become mine. It was the one revelation that opened my eyes. Have you ever heard the saying, “Not my monkeys, not my circus?”

      My advice to you is to speak with someone (a professional or someone who doesn’t have a stake in this situation) and maybe show them your post and the comments. Yes, you are somewhat doing that here but it’s different when you can be completely honest with someone who won’t be critical and can help you figure it out. Those who have commented here, from what they’re written, I see people who genuinely want what’s best for you. Some can be emotional because most of us, have been in your situation at one time or another. And we’re just thinking. ..”if only I had listened…, if only I took those signs seriously..”

      There are very telling signs that I see just from what you have written, how you respond to some comments and not others and what’s being left unsaid.

      You have done very well for yourself at such a young age. I think it would benefit you to really examine the situation ( not just the relationship but all of it). You have your whole life ahead of you. Take the time to figure it out. Because
      as you get older, the hours in a day, week or month seem to get shorter. There ia never enough time to get everything done. Invest in yourself and put YOU first. Like someone else said, you can’t take care of anything or anyone else, if you’re not in the best possible position that you can be in.

      You have a lot going on right now and you should think about what’s really going on. Ask yourself in 10, 15, or 20 years from now..where do you want to be?

      I wish you the best of luck!

    • Kristine says:

      I feel like I was reading about myself six years ago. I dated a man who was applying for med school but wasn’t getting accepted. He moved in (actually using an ultimatum, and I wasn’t ready to break up, so there it was) and our arrangement was half of utilities, since I owned the house and was paying stuff anyway. Money isn’t a thing for me so I didn’t care. He wanted to move, but I had a great life in my spot and already owned my house. I would have moved down to Florida, but not to another city in Michigan. I had my life plan. I had stuff figured out. His stuff just didn’t align. But it turned out that our lives were much better separately. We broke up, I moved to Florida, and I married a software engineer who has no debt and is a much more understanding and thoughtful partner.

      It hit too close to home for me to provide unbiased advice. So rather, I’d like to chime in with the following:

      You’ve got this. Whether with a partner or not, you’ve got this. You’re clearly smart, clearly have goals and plans, and you can conquer whatever you set your mind to. I’d say good luck, but you don’t need it. 🙂

    • Laurie Villotta says:

      Olivia: My oldest daughter has your name. 20 years ago I married a man that was an addictive gambler. He had nothing to his name and I stupidly supported him financially, emotionally and psychologically. I saw the red glaring lights, but went through with our wedding. We took our honeymoon on a cruise ship and the 2nd night of the cruise I found him gambling at casino. I told him that night we were done and went home and filed for divorce. He left me with a lot of debt and I was fortunate to work OT and got my finances back into shape quickly. I too bought the perfect home and was rocking my financial life. I knew I wanted children and wanted to adopt. My oldest daughter Olivia now 15 was played in my arms 12/26/2004 at 10 months and my 2nd daughter Claire now 12 was placed in my arms 11/22/2008 at 12mos both adopted from China. I can tell you that being a single mom has been the best ride of my life. Like you I have my family very close. I was 33&37 when my last daughter came home. I am now 48, will pay off my mortgage in 4 years and be completely debt free 2024. I hope my story will give you some thoughts about continuing your relationship or not. I see you as an amazing single mom that is financially set for life with a couple of kids that will change break your heart into a million pieces of love. You got this girl.

  3. Merav says:

    I too was alarmed by the way Olivia described their sharing of the work load (or rather lack of). I started my relationship in a similar way and although we stayed together and have had a child, the uneven sharing of various loads in our relationship has been a continuous and often critical problem between us. You seem to have a wonderful life on your own so please think carefully about what you truly want.
    All the best!

  4. Dorf says:

    Whosh, Olivia. I don’t think you would have written to the Frugalwoods and included the parts about your relationship unless you wanted to hear from internet strangers what your gut is telling you – “Never get involved with someone with more problems and less money than yourself.”
    Congratulations on all you’ve accomplished and good luck going forward.

    • Eva says:

      My thoughts exactly.
      Otherwise, I’m stunned by all the hard work you’ve already done, Olivia! Congratulations!

    • Alice says:

      Agreed. From what she wrote it seems like Olivia knows what the answer is but is looking for validation of her gut feelings. I felt like, in a way, this really wasn’t even a financial case study

      • Sandra, Italy says:

        I definitely agree 100% with what Alice says. Olivia, you deserve a relationship that works – not one that “COULD work if we had a lot of tough conversations and if he changed in several ways”. It’s not your job to “save” him, he’s a grown man! You have shown amazing strength of character in your other choices. Take care of yourself, go for your goals and eventually someone will come along that ticks all the right boxes 😊

        • Mary says:

          Totally agree here.

        • Doc says:

          Olivia, agreed. When I read about how you “put in 10 or 11 hours at the office and then come home and spend the evening reading emails from Jacob’s lawyer and looking over documents…I’m so burnt out” it breaks my heart and makes me SO angry. I’m biased because I’ve been through this situation (boyfriend leaving school, lots of debt, giving him free rent, emotional support, food, etc.) and I married said boyfriend anyway because he was sweet and madly in love with me and had “plans” to change. Marriage lasted 3.5 unhappy years, and ex-husband is still stuck where he was in ’08 when we first met. Please be ruthless in taking care of yourself; it is Jacob’s responsibility to take care of himself.

    • Michele says:

      I agree.

  5. Susan O’Donnell says:

    This is a very important case study for so many young people. As a mother of three “thirty-somethings”, I firmly believe Olivia’s struggles are quite common. What is uncommon is the depth at which she looked at her personal, financial and future life goals. Wow! That’s maturity right there-you go woman!
    Yes, I saw the same red flags on the personal/relationship side as Mrs FW noticed, and would really take those seriously. Olivia is a “caretaker”, in my opinion, and probably will be buoying her boyfriend the rest of her life if she decides to make him her life partner. That unequal relationship won’t hold together when that huge debt of his legally becomes both of their debt and THEY will need to find a way to pay for it. Money stress is the biggest reason for divorce/break-ups. His carefree and fun- loving attitude that makes you happy now will not satisfy that $290k loan.
    About that loan that will be paid after 10 years…
    My daughter is a Public Defender and has been for 10 years and was supposed to have the rest of her loan forgiven because of her public service. Guess what? It’s not happening. Much of what happens with these programs depends upon who is in charge at the government level. Student loans are NOT bankrupt-able(not really a word I know) so the boyfriend will have these loans forever. And they will be yours to if you marry.
    Has Olivia sat down with said boyfriend and asked what his future plans are regarding finances, family, location of home in the future? She is obviously adulting very well, but the real question is can he? On a side note, I also have a 33 yo daughter who is already divorced because she did not have these conversations with her fiancé’ and I feel partly responsible for not pointing out the red flags. Their issues were eerily similar to Olivia’s and her boyfriend’s, which is maybe why I’m compelled to comment.
    I wish her much success in her future and hope she can address these issues soon so she can have peace of mind that the correct decision is made, whichever way she goes with this.

    • Janis says:

      Jacob will probably not have these debts forever. When he finishes his medical residency and becomes a working physician, he will pretty quickly pay off his med school debt. Also, I don’t believe that legally student loans become a spouse’s responsibility since they were presumably incurred before the marriage.

      • Allie says:

        Yes but right now it’s “if” he becomes a working physician, not “when.” I’m in the medical field and getting fired from a residency is not common, and there is a non-zero chance that he won’t be able to find a residency spot/complete a residency. I hope for his sake that he can, but he needs to have a Plan A, B, C, D, E, F and G right now, and at least one of those plans needs to be a job that uses his current education and skills without being a licensed physician (Those jobs exist- in pharma, biotech, research, consulting to name a few).

  6. Amanda says:

    Dear Olivia,

    I really enjoyed reading your case study and wow you are in a good place (much better than me!) financially. I just want to give a snippet of my story in terms of being married to a man with ADHD (recently diagnosed ) with a different financial outlook then me. We have been together for 17 years now and have two beautiful children, and I love my husband very much. However, there is no denying that my life is very different then what it would have been if I had not married him. Financially, we are in a lot of debt and I have been in some seriously weird situations regarding money. Not all of this is his fault of course- I am also to blame but certainly his difficulties have contributed. I agree with your co-worker on the “does anything change”? We have had excellent communication for 17 years. But we have also had very little change (and some dishonesty on his part out of fear), and I understand this to part of the symtoms. I feel like I am sounding bitter here- I am not- I am very grateful for the life we have together. But please go into this with your eyes open. If you haven’t already- read up on ADHD so that you know how best you can support him. If you know all this already please ignore this and just chalk it up to me thinking what I would have liked someone to tell me 17 years ago. I would have still married him, just with a bit more knowledge and caution.

    • Olivia says:

      Thank you Amanda! This is so helpful. I’m glad to hear that despite your challenges you still enjoy life together.

      • Amanda says:

        We absolutely do and I can’t imagine my life without him! Best of luck with your journey ahead. Also, a resource that really helped me is the website additude where they have a lot of information about being in a relationship with someone with ADHD. Sending you lots of love and positive vibes all the way from Sweden!

  7. Jen says:

    First, go to yoga today and keep up your practice. It will help to destress you and give you mental clarity on the decisions you need to make. And why not start pursuing that yoga teacher training? Self-care is the most important thing we do. 🙂

    Jacob needs to take responsibility for his situation. He needs to get a part time job flipping burgers until something better comes along. He should pay rent (or move out) and deal with his legal problems without your assistance – he can contact your local social services to find free/low cost legal assistance. All financial decisions and future plans should be solely based on your individual needs for the foreseeable future. And I don’t think a long distance relationship will have a big negative impact on your finances as the two of you will equally split the cost of travel, cellphone bills, etc.

    You said you spent a lot of time alone before meeting Jacob. And you said you want children. But you can definitely be lonely while in a committed relationship and you can have children at any age until you reach menopause. I don’t think you should let those two factors influence your current situation.

    • Melissa says:

      I wish I had a “this” GIF to give you. Because I agree 100% as someone who has been there and had to rebuild her life after that failed relationship. Take care of yourself first! Loving someone does not mean drowning with them.

      • Jo says:

        This is me too. He was a good man with many good attributes, but AHDH, albeit undiagnosed, but it’s a long, long path downhill which will suck your soul as you try to help him. You are not helping him by trying to compensate for his deficiencies. He needs to do that, not you. I am divorced now and life is better, but I so wish I had been as wise as you and that I had sought advice then.

    • Alyson says:

      I agree 100% with this person, with the other commenters who feel caution for you regarding this relationship, and with Mrs Frugalwoods. Lots of red flags around this likely kind fun man. I married late, was single for a very long time and had my children late. I love my family and hard relationship choices prior to this relationship that got me here. I have been a frugal, academic person in a medical field for 20 years…I understand your post well. You love your home, your job and your work/home balance. All of these have been, as it is inferred by most readers, not only negatively impacted, but also not automatically well considered by your new partner. The key word here is “automatically.” When you place responsibility back onto your partner for his own legal battle, finances and personal choices of his that lead him to his situation, you will see how that goes and if he has the capacity to see how his choices deeply affect you and the situation. This will then answer your questions about your financial situation more easily. It would be an important piece of seeing how much he is able to demonstrate his caring for your well being as much as his own. I am only guessing here he has no idea the heavy burden of responsibility he has transferred to you (financial, legal, emotional support and planning.) Your confidence in your abilities in work and caregiving need to match your confidence in the fact that your gifts with be a strength and will be respected by the right partner. You sound lovely and I am betting your are a smart kind caring friend to all you meet.

    • Kim says:

      I 1000% agree with everything Jen said above! Reading through this case study, I was becoming more and more alarmed for Olivia. Red flags everywhere about their relationship. It seems like Olivia is giving, giving, giving, and Jacob is taking, taking, taking. There seems to be no partnership whatsoever. As someone currently in a very lonely marriage and thinking about my options, I would much prefer to be alone and accountable to only myself. Olivia, you have accomplished SO MUCH on your own and at a young age and I am beyond impressed with you! It honestly sounds to me like you would be better off without Jacob and all his issues. I’m sorry if that’s putting it too bluntly.

    • Stacey says:

      So much this.

    • Kristine says:

      This. A woman I consider a mentor has two children, one from a marriage and alone. She wishes she had both alone, because sharing holidays and dealing with his desires for the older child is a serious PITA. And the older child isn’t enthusiastic about it, either. She overhears comments between sisters that “having a dad sucks.” That may be big sister trying to soothe little sister, but it’s definitely harder on everyone.

    • L. says:

      I really don’t think anyone would give Jacob pro bono legal services to appeal his termination from residency. And I also think flipping burgers would make only the most pitifully miniature dent in his loans that it would be pointless. Why not explore a career he can do with an MD like medical equipment sales? In his shoes I think I would devote half my time and effort into finding a new residency, and half to figuring out a new career path with near-term job opportunities.

      As for Olivia, when Jacob gets a new residency and has to move hundreds or thousands of miles away, does that make you sad and desperate to rearrange your life to be with him, or kind of relieved because you can cut ties and aren’t leaving him when he’s down? I think that’s your answer on whether he’s a keeper.

      • Chelsea says:

        That’s a great way to look at it. At the end of the day, none of us can really know what path is the right choice for you, Olivia. But questions like the one posed by L can help you assess which way points to your own “North Star.” (If you haven’t read “Finding Your Own North Star” by Martha Beck, I highly recommend it.) It sounds like you’re already on sound financial ground and like you have a good idea of what you want your life to look like, from a lifestyle perspective. The real question is, are you willing to change that, or how much are you willing to change that, to stay with your boyfriend? And does that take you further down your path to happiness or further away from it? There’s another book I’d suggest, “Too Good to Leave, Too Bad to Stay.” It dives into some areas in which compatibility is extremely important to the overall success of the relationship. Lastly, I’m not sure if this would be helpful with someone with ADHD, but “Fair Play” by Eve Rodsky can help you assess who is holding which household tasks – right now it sounds like some tasks, like making meals, aren’t really being held by either of you right now, but you wish it were more of a priority in your lives so you could save more money!

        I know you’re strapped for time right now, so book suggestions may not seem like the most helpful thing. I find that reading often gives me new ideas, though, or helps me clarify my thoughts.

        Good luck on your journey! You’re doing great!

  8. Lynn says:

    How long would you be okay with things in your relationship being *exactly* how they are? 1 week? 1 year? 10 years? The rest of your life?
    Fair warning, I’ve had a Jacob, so that colors my perspective. I think lots of women have. We’ve been culturally conditioned to accept behavior like this as the price of admission in relationships since the dawn of time. We’ve also been told that being partnered up is the be-all and end-all. It’s not.
    It sounds to me like Jacob has a great deal going – a supportive partner, minimal expenses (even though he’s not particularly frugal), someone to review his legal situation and doesn’t question his part in it. By the way, what’s he doing to address the underlying factors so he doesn’t become a twice-fired medical resident? But… what about this benefits the you-half of this partnership?
    This is huge: “Although I will admit, I told a co-worker once that we had great communication and her response was “but does anything *change*?” – and that’s something that certainly needs to happen (that, again, we’ve talked about).”
    You are a part-owner in a red flag FACTORY and your financial acuity throughout it all is commendable. I’m especially glad that you have a solid emergency fund. Don’t be afraid to use it if you get to the point where you need to dislodge Jacob from your house/life.

    • Georgia says:

      Love this comment! And if you Google “women marrying themselves,” you’ll find that you’re in very good singleton company these days!

      • Melissa says:

        Agreed to both Ladies! Also recommend reading: “Spinster” and “All the Single Ladies”. Both were my go to when I was single. I was completely content when I was single, and I’m still a very independent child-free wife and step-mom.

  9. Carrie says:

    Hi Olivia
    I am so impressed by you. I think you will be fine.

    I was recently divorced after 29 years of marriage. So, I may be biased.

    Do NOT get married. Legally, it creates a mess. It is very expensive to get out of and really does not have much of an upside legally or financially.

    You can and should stay in a relationship that brings you joy. No relationship is perfect. In today’s world you can stay together without the legal bindings of a marriage license.

    Also, Jacob should be at least be working part time and paying for more, perhaps utilities.

    You are doing an amazing job keeping your expenses low. I am particularly impressed by your eating out budget.

    Good luck to you.

  10. Mai says:

    Generally 403b is safer for pre tax savings than a 457. I would considering maxing that one out first.

    Medicine in general is a very safe high earning field of Jacob ever settles in and completes his training. Even if he doesn’t, the fact he has some years (assuming he finished intern year) he can still get a license and work in some places (urgent care, VA facilities) and that would be higher income.
    Regardless, marry for compatibility (the debt doesn’t scare me but his non-frugal Tendencies are a red flag)
    Coming from a high debt (but frugal living) two doc family.

    • Olivia says:

      Hi Mai, This is helpful – thank you. Yes, he finished intern year and doing this is on the table. He hasn’t moved on this yet because in the initial firing they gave him 11.5 months of training, but in the final determination they granted him 13.5 I believe, which is a huge win. Now that we have that, he can apply to a medical license and try to get a position at an urgent care facility while he tries to transfer as well.

      I don’t understand your “safer” comment regarding a 403b – I’d be interested to hear more about your understanding of this?

      • Thomas A Waffle says:

        A 457 account through a non-government job can be considered risky because the money in the account is not held in trust – it is not legally all your money yet (you maybe work for a state university which would be governmental). Since the account is not held in trust, if the employer goes under or has other financial trouble the 457 can be used to pay back creditors. Do a quick google search on 457b risks just so you know what types of accounts you hold and the benefits and risks.

        My spouse has a 457 through the state because he works for a municipal city agency and we are deferring the max this year. We plan to use this money combined with non-retirement investments to bridge the time between when we stop working and when we’re eligible to withdraw from retirement accounts. I think having a 457 is a great benefit for savings diversification.

  11. Gina says:

    Woosh- Mrs FW is right on point here! Olivia – your plans for the future sound wonderful and you really come across as a very conscientious, hardworking, responsible person and you are doing brilliantly. Any person ought to want to snap you up in a heartbeat! I’m not hearing equality though: Jacob pays no rent, just groceries and yet Jacob wants to go out to eat out a lot, doesn’t prep dinner, and wants a fancy restaurant for his birthday? No girl, no. I get the sense of possibly charismatic and brilliant, fun and charming but you seem to be contributing a heck of a lot to this. It sounds like the future isn’t in any way your decision: If Jacob’s future studies are across country, he’ll move and really your only choices are if you follow whatever future geographical/vacation/restaurant plans he decided, or if you say no, then that’s it over. Perhaps this isn’t the case but this is how it seems to me to be presented. And the bonus in this future planning is that if he decides he wants to marry, you get the 290k (or by that point 500k?) debts.
    Right now, continue to be true to yourself. Look after yourself nutritionally, get to the yoga studio and don’t lavish money on eating out if you actually really want to pay down on the mortgage. A person who loves you and appreciates you will respect your need for health and well-being and will not want you to sacrifice this. There are always compromises in relationships it’s true but both branches must bend in the wind. Good luck and once again I’m really impressed by your achievements

    • Kristine says:

      I thought that was odd too. My boyfriends and now husband (granted a joint account lol!) always foot the bill when we go out. I was raised to expect it, by my loving and wonderful family. I “return” with nice homemade meals. I would think, if you pay *everything else* and then some, that he’d be all over those eating out bills. Your eating out line should be zero. That’s like groceries. It all goes together.

  12. Georgia says:

    Hi, Olivia!
    I feel like you’re going to get more relationship advice than financial on this one…! 🙂
    Honestly, I don’t know much about any of your savement/investment systems, so I can’t weigh in on that one all that much, except to say WOW YOU ARE DOING AWESOME and should be totally proud of yourself! Jealous over here!
    Okay…about the relationship. I am so very, very happy that Mrs FW weighed in with such clarity because she says basically what I felt as I was reading.
    Part of why I agree with her is because I’m a writer and I love thinking about writing and one of the funniest things that happens is when you re-read something you wrote with fresh eyes and it suddenly hits you—THIS is what I really think?? It’s almost like getting insight into someone else’s mind. So I’d suggest, if I may, really analysing what you wrote here, taking it apart, and seeing what it (you) is saying back to you.
    On another note, I know that you can’t change someone, but being married myself I can tell you from my own very subjective experience that different aspects of people’s personlities can expand or contract, especially under certain circumstances. Marriage is one of those circumstances. Job loss/stress is another. Having children, as Mrs FW said, is HUGE. Throughout your life with Jacob, you’ll go through one after another of these “job-loss-type” stretching and contracting scenarios. Because this definitely isn’t the last one. How does that make you feel?
    I’m going to attach a hilarious link to a thing I love (love!) about ‘the mental load.’ Not sure if you’ve heard of it, but it’s great.
    I truly wish you all the best—your situation is complex and I hope you can take some time to breathe and rest and look at it all from a bigger perspective. Get back to that yoga, girl! I know my case study with Mrs FW helped a lot, and I wish the same for you!

  13. Lauren says:

    Long time reader, first time commenter. Olivia, I feel like we have a lot in common! I too am striving to rid myself of PMI after purchasing my house at a very similar price point last year. I also have a mini-split system in half of my house, and it is fantastic. You will be very happy with that choice! Additionally, have you looked in to combining your auto insurance with your homeowner’s insurance? This might not be possible due to the housing cooperative, but my car insurance (also for an older model Corolla!) was cut in half by bundling.

    While reading this, some things about your relationship definitely stuck out to me. I can sympathize with not being on the same financial page as your partner as well as your point that eating out seems to be compounded when you start dating someone! I agree with Mrs. Frugalwoods on a lot of her observations, particularly that there seems to be a considerable amount of uncertainty when you think about a potential future for you and Jacob. I am the primary earner between my boyfriend and I; he works part-time in the service industry and is currently taking college classes for the first time (which I will be helping to pay for in the upcoming years). Because I am generally busier with work, he takes on a considerable amount of the household chores. This is helpful to us both because I don’t feel as swamped, and it helps him to feel like he’s contributing to our home in a way that is not tied to his income. I would suggest having that discussion with Jacob.

    My main takeaway and advice, however, is that if you are not absolutely sure about Jacob as your partner, it sounds like you would be better off cutting ties. Despite the financial complications my boyfriend has added to my life, I have never once considered that to be a stumbling block when it comes to our overall relationship. I know that being with him has required me to adjust my long term financial plan, but I cannot possibly imagine a future without him, and am willing to make whatever compromises are required for that to happen. My philosophy prior to meeting him was “you’ll never be 100% sure about anyone you’re with, the good just has to outweigh the bad.” That has absolutely changed and I know now that it IS possible to be 100% sure. I don’t want you to sell yourself short on a relationship– you sound like a badass, independent woman that would be fine on your own OR open to the possibility of a partner you’re sure about down the road.

    Best of luck to you, Olivia!

    • Caroline Bowman says:

      this is such a great perspective. Of course being with someone who doesn’t earn very much or is a bit behind you in terms of life goals is NOT a deal-breaker. If the relationship works and you are genuinely really happy and committed together, then that’s better than many people can ever have.

      But that’s the thing, in your case, the person who is working less and has more time, contributes in other ways around household admin, cooking and so on. That’s a reasonable trade. You have shared goals and a bit of a time line re where it’s all headed, also ideal. Who earns more is not what’s critical, it’s the shared attitude towards life and equity between the two of you that’s so important and in Olivia and Jacob’s case, I don’t see it.

  14. All For Now says:

    I agree completely with Mrs. F, including the PMI and Mr. Good Enough (I just read it – eye-opening!). I’ve been through the stressed and anxious yet fun and laughing relationship. It blew up in the end in a spectacular and financially draining fashion. While I know the allure of having someone and also you’re probably thinking about kids, NOW is the best time to be looking (read the book to see what I’m talking about!). Look to his past to see his future. If he’s getting close to 40 and no savings, lots of debt, spends money and not looking for a job (yes, what happened to him is awful – it seems though that he’s not addressing how he got to that situation, which means it won’t be corrected for the next job). My advice is let him find another residency and do not move with him. If you find you can’t live without him, let him do his residency and see if he makes the changes necessary. Also, DO NOT let him pay rent or anything for the house. He’s used to dealing with lawyers so potentially could come after your place especially if you live together for some time. I do recommend having kids no matter what, but I’d wait 6-7 years. Your employer may provide fertility support, including freezing your eggs. I’d check into that. Also, as a single mom and as much as I love my kids, having just 1 is MUCH easier than having 2 unless you have a lot of support from your family or someone else. Finally, is Jacob taking medication? Both my kids have neuro differences. If he’s not taking ADHD medication (life altering for my child! Also expensive!) or doing other things to help with ADHD as well as the processing, you can expect the same thing to happen THROUGHOUT HIS LIFE. One last thing – watch for the surprise engagement or something else that would saddle you with his challenges. I’m all for helping people, but if my daughter was dating him, I’d counsel her to wait for him to start helping himself before agreeing to a long-term future with him. Relationships like this are not easy. Check in with your family and friends, who while they may not be immediately forthcoming, may provide their insights if you share some of your concerns. Best to you.

    • Bev says:

      My husband has ADHD and this is true, it will impact you both your whole life and it is amplified when financial or child decisions come into play. Also, something like being (likely unfairly) fired for issues caused by ADHD is something that can happen again because it’s very difficult to modify behavior with this disorder, if not impossible. With ADHD therapy often doesn’t help and medication had some serious side effects. It’s a hard life with these smart, wonderful ADHD people. Take it on only if you are sure because it will not get better. You gotta love them as they are!

      • All For Now says:

        I’m sorry, but that’s not entirely true. Medication does work (yes, there can be side effects but that’s why you need a good doctor), so do behavioral modification techniques and so does matching work with the positive skills the person often has. For example, I am a consultant so moving from project to project fits exactly with my strengths. There are many other things that can help though I agree do not overcome. There’s also a genetic component, so good probability of kids inheriting it.

        • All For Now says:

          Actually, sorry to @ Bev. Her overall advice is spot on. I read it too fast :(.

        • Bev says:

          Hi @All For Now – thanks for saying you read too fast but overall agree. ADHD is a sensitive topic and maybe I wrote it too fast! My [ADHD] husband is amazing but he’s not motivated to modify behavior or take medication because he is a creative-type in a creative industry. His behavior makes him successful at work and I recognize that his brain is just wired differently through no fault of his own. I wish he would, but I love him for who he is. We split chores equally and he is financially responsible so a great partner overall.

    • Blair says:

      “Also, DO NOT let him pay rent or anything for the house. He’s used to dealing with lawyers so potentially could come after your place especially if you live together for some time.”

      I don’t understand this comment. How could he possibly have a legal claim on her house?

      • Jen says:

        “palimony”- google it

      • Victoria says:

        If a person can prove they pay something toward the house or has otherwise contributed then they can sometimes make a claim to some equity in the property, and may have some sort of squatting rights. The US won’t be the same as mine in the U.K., but it’s a valid worry.

  15. ann says:

    Hi Olivia – SO impressed by your life -wow! Congrats on so many things – being responsible, debt-free, proactively planning for your career, education, having a family, etc, and finding an affordable home to buy in such an expensive real estate market.

    I have one suggestion that I sincerely hope is helpful. You may want to read about adult co-dependence. I myself have a co-dependent personality and spent years trying to fix my family member’s problems. A few years ago I learned about co-dependence and it allowed me to fully realize and accept that I am not responsible for other people’s problems. When I let go of their problems, their lives actually improved as they had to take full responsibility for themselves; I thought I was helping but it turns out I was holding them back. I definitely DO NOT know enough about your situation to assume it’s the same but just wanted to share my own experience in case it is helpful.

    Best wishes.

    • cupcake says:

      Ann, agreed! Reading Codependent No More has changed my life and relationships. Highly reccomend. Much of the book discusses people with alcoholic partners, but if you can think about it in terms of other scenarios, it is abundantly freeing.

  16. DCC says:

    Olivia- my personal vote is to consider whether you want to stay with Jacob and have children with him first, regardless of all financial decisions. The whole point of FI is being free – and I can’t imagine any more important way than to be with someone you love (IF that’s what you do want!). There is huge benefit in having a partner in life and a partner for raising your kids – with my second on the way right now I cannot at all imagine doing this all alone. If you do decide to do it alone you will need to build an exceptional community around you. I am also – with my second kid on the way- a new physician with close to 400K in student debt! But honestly, I don’t worry about it at all. It is all federal debt which is highly protected, in an income based repayment program (meaning when you make little you don’t pay and once you’re in the program long enough the remainder is forgiven). Not all debt is the same at all and not all of it need scare you. Even having an MD and without finishing residency I bet Jacob is pretty employable. If he seems to be not only smart but a bit financially savvy he will get back in his feet. You can also opt to stay together, have kids together, and not get married and not take on his debt, if that is palatable to you both, it has been the right financial decision for me and my parter. I wish you luck in figuring out what is truly important to you.

    • Olivia says:

      DCC – thank you for this comment! I was put off at the time from diving too much into what people were posting as it seemed like most were telling me to leave my partner (and not always with the best tone) and reading hundreds of posts about that wasn’t really doing it for my mental health at the time. Sigh. But I really appreciate you taking the time to leave this comment. We honestly haven’t talked at all about the potential of having kids and not getting married, but you make good points. I do have a good friend from college who does family law so I was planning on reaching out to have him draw up a prenup when the time is right. Jacobs loans are also in IBR, so we will file separately when we get married.

      There’s also a locational aspect to this that I’m not sure many people got – I think he would be a GREAT doctor… not in a major, metro, east coast city. Somewhere in the south or rural New England where the pace is slower and he can take more time with his patients would be a much better fit given his challenges and strengths. I love this area and would hate to move, but wanting him to be successful and the difference he can make as a doctor would absolutely be worth it (after the point of needing lots of grandparent help with babies)! Jacob is a huge child (haha) and will be a GREAT parent, and that’s one of my favorite things about him. We compliment each other very well. 🙂

  17. Jaz says:

    Hi Olivia, I think you should definitely take all of Mrs. FW’s advice to heart, but it seems you’re really craving more input on how to deal with an unemployed partner and I can speak to that! My husband was recently unemployed for a full year. Similar to Jacob, he chose to not take “any” job in order to fully focus on his career path. My situation was different because we are married and have joint finances, but as far as the emotional aspects of supporting an unemployed partner here is my advice:
    -Put your oxygen mask on first! You need to support yourself in order to give meaningful support to others. You seem to be prioritizing others (Jacob, work) before yourself. If Jacob wants you to go over documents for him, tell him you will after you do yoga or after you cook up a big pot of chili/soup/stirfry for the week. Assess wether your inability to take a timely lunch break at work is actually because of non-negotiable work needs or because of pressure you put on yourself.
    -That said, if someone is living rent-free in your home and is not working and is able-bodied you should have a lot more support from them! I know that he’s going through it right now, but I think that feeling useful can be super helpful to the emotional well-being of an unemployed person. My husband and I joke that when he was unemployed I didn’t lift a finger for an entire year. Now that he is working, the household chores definitely skew more to me since I work from home, but he literally learned to cook when he was unemployed. Even if Jacob isn’t culinary minded, he can learn simple recipes (the budgetbytes site is great for this and has clear step-by-step instructions)
    -It sounds like you are a very practical person and you are eager to help in tangible ways. The truth is supporting someone emotionally through unemployment doesn’t mean you have to help them in their job search, read over their applications, etc. Friends, family members and even paid consultants can do those things. As a partner you are in a position to help them maintain their sense of self through a time that can be depressing or demoralizing. Plan cheap dates (free museum nights, cook at home and go out just for dessert) during which you DON’T talk about his job and residency applications at all. Careers are so intrinsic to our identities, but challenge him to talk about goals that are not work-related. (this has the added bonus of helping you learn about him more deeply because it sounds like you’re still figuring out if the kinds of lives you want to lead are compatible.)
    -Be realistic about your own feelings, communicate them, and don’t let others opinions sway you too much from your own truth. I had friends who were really side-eying my husband’s unemployment once it went on for a few months, but I knew that I was fine with it lasting up to a year. People tend to see unemployment as a crisis and it was really helpful to him that I was extremely calm about it.

    Your home and neighborhood and family sound so lovely. Don’t forget to enjoy them while you’re figuring out the future 🙂

    • Rachel S says:

      That’s great advice. Olivia mentioned not having time to prep meals- that could be a good task for Jacob while he is unemployed. That would help with Olivia’s desire for frugality and most likely would help the relationship.

  18. Mina says:

    Is Jacob really pulling his weight here? He is unemployed and you’re coming back from a long day’s work and having to help with his life admin plus still seem to be taking accountability for traditional ‘wife work’ like what you eat the next day. And as he’s off work is there no side gig he can do, to be able to kick you $300 or so to plug the deficit (some of which is being caused by the increased living costs of a partner!)? If you were fired, would you expect him to do the same for you or would you be insisting on contributing financially/by taking on some extra burden at home? It sounds like you’re bearing much of the cost – financially, emotionally, and otherwise – of his unemployment and he’s not doing much to offset there.

    I was also a little alarmed to hear you say you’d *have* to sell your house, and eventually buy into the holiday home LLC. A good partnership either involves good alignment or some compromise – Jacob might want to think about where he is willing to compromise to meet your needs and goals.

    My husband was off work with stress for a month (thankfully paid!) and the only silver lining was that I had a month of not having to do any cooking or housework because he was home all the time. It sounds like there is an imbalance of effort, considering how much you’re helping him out right now. I know what it’s like to be alone, and to be sad about it, but please don’t let that be a driving factor in your decisions about *who* you stay in a relationship with.

  19. Monica says:

    I am also a 330-something in DC who moved in with a partner during his unemployment several years ago, so I’ll speak to this area. I really understand the feelings of stress and crisis that happen and last for months, and how those things can really affect you as the financial provider. My partner and I were already on the path to moving in together when he was fired from his job for reasons where he was entirely at fault. He was a crappy employee in that job! This lasted about 4 months until he found a new role in a related field, but totally different working environment (changed from corporate lobbying to nonprofit advocacy). And in the years since, he’s absolutely flourished in his new role- consistent raises, promotions, increased responsibility. He really found his passion and is 100% a different employee.

    During this time, I was also doubting a lot about his ability to be a good partner in all the boring, practical ways like financial stability, which was especially important for me as I was (and am) in no where near as good of a financial spot as you! But seeing his transformation helped a lot. I think it’s really important to keep in mind the ability of someone to change for the better.

    That being said, it is valid to consider how a person responds in crisis and think about their character. My partner was utterly embarrassed to be relying on me for financial support. Even as he was reeling from the emotional consequences of his actions, he really stepped it up for us in our house- learning to cook, doing a lot of cleaning, and be really open about what steps he was taking to rectify the situation (applications, networking, etc). Of course I was involved in his job search, like you are looking over his legal papers. I think that’s good and that’s something partners should do. I also didn’t charge him rent, but he did contribute to groceries and bills from his savings. We drastically cut out restaurants and other unnecessary expenses. This worked for us, so I don’t think you’re doing anything wrong by not charging him rent while you’re not hurting for the cash.

    Based on your letter, Olivia, I wonder about your boyfriend’s relationship to money pre-crisis. Is he from a wealthy family where there are always people who could provide for him during times like this? Is he not? Is he happy coasting and racking up debt now with the assumption that once a doctor, his salary will cover all this debt? Neither me or my partner came from family who could help us out a lot, but were always very generous with what they could give. So for him, having to rely on others was really difficult and embarrassing. It doesn’t sound like your partner minds relying on you, and isn’t doing much to lessen the burden. Asking for expensive theme park tickets for his birthday, still wanting to go to restaurants. (maybe because it lessens his grocery bill)… I don’t know. I think there is a lot to think about in terms of how he is handling himself and caring for you and your collective future in this time.

    • Olivia says:

      Hi Monica, thanks for this comment and apologies for not having the time to respond when I initially had the case study posted. I really appreciate you sharing this story, and now that we are on the other side of the unemployment, I identify with it even more! Unlike your partner switching industries for similar work, Jacob moved to a different part of the country and has been experiencing a similar change in how leadership perceives him. In the DC area, we prioritize the administrative, financial aspects of almost every field. Where Jacob moved, and Jacob as a person, very much prioritizes the personal relationships more. Not that they don’t care about the financial and administrative… but Jacob has also become a lot more timely with these things because he has certainly learned how important they are both to his future (based on his experience) and how important they are to his current employer (who does a much better job of on boarding and explaining the system/culture/goals of the organization and how these things support their overall goals, even though they aren’t as “fun” as helping patients).

      Jacob’s family is certainly wealthier than mine, although I don’t have a good grasp of what this actually means. In practice, they buy nicer wines than we do – we stick to TJs $7 max and they are more like $50-$70 – and they also buy very fancy cheese. 🙂 But they have a small, two bedroom house, I haven’t known them to take an international vacation yet, and seem to mostly read and listen to NPR for their hobbies. I do think he knows that he could rely on them for backup – his sister thought that he should move home to help support them with some mobility and health issues since he wasn’t working anyway. I think because his loans are federal, he’s in IBR, and is pursuing PSLF, the high debt load doesn’t weigh on him as much as it does me given my upbringing (I am doing more reading and my worry is decreasing here). He doesn’t have any other debt and really doesn’t have the spending habits to get there, despite what I shared here. I don’t think he was embarrassed to be relying on me financially, but he was pretty embarrassed about his ability to understand and process the other things I was helping him with (how quickly I can read over the legal documents, how quickly I can write professional emails, etc). For him, given the stakes, he really wanted to take a lot of this on and be in control and know what was happening… but given his ADHD and processing challenges and the general failure of medschool to teach you how to write, this produced a lot of anxiety and took probably 5x as long as it took me, at least. Now, whenever he needs to send a professional email though (licensing, whathaveyou) he always BCCs me and calls me and is like “did you see my email? I did so good, right? Aren’t you impressed by all my progress!?” Yes baby, I did and I am. 🙂

  20. JM says:

    “I also want to acknowledge that this is a rough time for Jacob given his unemployment. And sticking with someone during a rough time isn’t easy…if she doesn’t want to be with him, but feels beholden to him because she’s supporting him financially, then she needs to prioritize her own needs and extract herself from the relationship. ***As she noted, they are not engaged or married and she is not responsible for him.”***
    Quoting those most excellent words from Mrs. FW above b/c they echo my own thoughts exactly upon reading this…
    Apart from the actual finances (Most impressive,Olivia!) I truly believe that a good marriage/partnership can only be based on equals working together. Based on Olivia’s description (again,noting it’s partial) It seems to me that Olivia has worked HARD to get herself in a good place in life,and is feeling the stress of allowing someone (whom she cares about) to possibly upend all of it. (based on his current choices in life)
    I particularly agree with the thought that while there may be many positives about him, She is not responsible for his life,his choices,or his debts. That means being supportive,and kind and loving without taking on the responsibility of his life issues,be they medical or financial. As an equal adult, those things are his responsibility,esp. since they aren’t married.
    And as much as you may like or love a person, you still have a choice about what you choose to add to your own future- People always show you who they are (vs. telling you) so true communication is really about paying attention to the real signals being sent.
    It sounds like Jacob and Olivia have some fun together,and enjoy each others company.
    Whether Olivia chooses to allow Jacob fully into her life as a married partner is up to her, but it’s wise to protect what you’ve built so far in all ways.
    Again quoting Mrs. FW -Are you willing to give up on some of your personal and financial goals in order to be with him? Or, would you be happier pursuing the goals you’ve outlined potentially on your own?” Best wishes for you in your journey!

  21. Amanda says:

    Hello Olivia,

    I agree with Mrs. FW and Dave. Olivia, you have definitely accomplished financial stats to be proud of and should celebrate those achievements! As pointed out by others, you are better off than most people 10 or even 20 years older.

    Your relationship and future with Jacob is a very personal decision, but I will make one comment/observation. You seem very independent and able to live a happy and content life without a partner, which is a good thing. Until my late 30s, I was in the same position as you. By that point, I realized that if I was going to have a partner, he really needed to be on the same page as me with his goals, preferences and outlook on life. Fortunately, we found each other, however it took a few attempts (read: short-term, one sided relationships) before I met my match. Between those “attempts” of finding my partner is the timeframe when all of my financial, career and personal goals solidified. If you are happy with the status quo, there is nothing wrong with continuing on with what you are doing both personally and financially. As you stated, there is a good possibility Jacob will need to move out of state and that will most likely be a make or break point for your relationship. Sometimes, we put too much pressure on ourselves to know the right answer or decision NOW and it’s not always necessary! You’ve made good decisions so far and are not in any sort of financial or personal crisis from what I can tell.

    One last thought that struck me when reading your post: wanting to become a mother soon. You have so many commendable goals and hopes. To paraphrase, you are wanting to pursue a PhD to delve deeper into subjects and not just “get through it.” You mention possibly getting into AmeriCorps, doing yoga 5 days a week and spending significant time cooking and reading. Those all sound divine to me! However, if you end up becoming a single parent, some of these goals you mention will most likely need to take a backseat or become lower priority for a time while you are raising your child. I just wanted to add that if only to help you put your timelines into perspective.

  22. C says:

    I think you and Jacob should live separately as soon as possible. This is NOT a judgement of him or your relationship. It would allow you to decompress and grow your relationship without such a focus on the future. Right now you’re supporting him in ways that take away from your wellbeing: emotionally, legally (reviewing the documents at night and being exhausted), and financially to some extent. You live each other so he should understand and why would it break you up?

    • Ca says:

      Also, it may be a confidence boost for him, taking care of himself and having a partner with whom he can have focus on the fun, rather than serious stuff. Of course you have fun now, but realistically this situation and the financial / location questions are looming large over you both right now.

  23. Lizzie says:

    Olivia — congratulations on accomplishing so much at 31. I’m 52 and never married. I own a home in DC that I bought when I was 27. I understand the societal pressures of being single, and how exciting it can be to meet someone and call him your boyfriend. But you are sacrificing too much to be with this guy. You may not see it now, but you will in 10 years. He needs to figure out all of his stuff – not you. Charge him $100 in rent every month. You’re giving him a place to live and that’s enough support. Put your energy towards your goals. Don’t put Jacob ahead of everything else. Good luck!

  24. Marilyn says:

    Dear Olivia, you haven’t mentioned the REASON why Jacob was fired from his medical training program. And, if he is seeking admittance to yet another program, is this his only option? What if he can’t gain admission or isn’t able to deal with the stress of a grueling residency? At 36, does he have a work history in anything else or is this it for him? Why are you working harder at fixing Jacob than he is?

    Bringing children into this unstable mix would immediately devolve into chaos, poverty and resentment. Should he remain unemployed, with $300,000 in student loan debt (which is not dischargable), what will you do if you marry? Will he take on child care responsibly while you are working long hours at work? BTW, infant and toddler caretaking is probably the most stressful job in the world.

    Jacob might look like a tall drink in the desert after a long boyfriend dry spell, but there is no room for more self-sufficient partners in your life until you set Jacob free.

    Sorry if my comments might sound judgmental to you and others, but you are on the precipice of a cliff, compounded by emotions blunting reasoning ability, and I hope you can envision the aftermath of what you decide to do in the present.

    • Kim says:

      Well said, Marilyn. Totally agree with you.

    • Sandra, Italy says:

      Blunt but so to the point, I agree with Marilyn.

    • Roberta says:

      Completely agree with Marilyn. As a registered nurse of over 30 years, I have seen MANY medical students/Interns/residents come through several different hospitals. I have also never seen one who was “fired” (it’s extremely rare anyway) without a serious reason. The person was either dishonest, disrespectful of patients, physicians,or co-workers, or otherwise ill-suited for medicine. I also still remember being young and in love, it’s exciting and you want that feeling to last and to be reciprocated. I don’t see this happening in your personal relationship. It seems to me that Jacob has a good measure of narcissism in addition to ADHD. You seem to have so much going right for you, you’re smart and wise in so many ways. My advice, yours to take or not, is run from this relationship like your life and future depends on it.

  25. Kristen says:

    It seems my opinion of the situation is quite different from other commenters. I agree Olivia should, of course, only choose to make a life-long commitment like marrying Jacob if she feels he is the one for her, but I disagree about his debt being such a huge factor. First off, many many medical professionals and physicians come out of school with similar levels of debt. And secondly, since it sounds like Jacob will eventually get a new residency, he will end up with an extremely stable job with a very high income (enough low paid doctors often make 180,000-200,000). If Jacob is willing to live frugally for a few years and put 100% of his discretionary income towards his debt he could pay it off fairly quickly with that high of income. While I realize this doesn’t solve the long-distance concern, it does address the concern regarding his debt. And, once he is debt-free that high income can be used to save, invest, or otherwise go towards early retirement for Olivia (if she did decide he was the one for her).

    • Caroline Bowman says:

      My concern would be that at 36, he’s been fired from a program. Why?

      How long is all this going to take, given that he was fired in May and it’s now December? Presumably he will shortly be 37. Him working towards getting rid of debts couldn’t feasibly happen till… quite some time. It feels like he’s on quite a good wicket at the moment. She seems to be doing a huge, huge proportion of everything life-related and he just gives her grocery money.

    • Melissa says:

      I think that my concern isn’t the debt for medical school itself. But I think being “fired” from residency is a huge red flag. In addition, his income is contingent on him getting another residency. And completing residency. To me this is less about the money and more about the follow through and ability to be a contributing member of the household.

      • Olivia says:

        Just as a note, technically it was a contract non-renewal, not a firing. I have since learned the critical importance of this difference and apologize if I was flippant with my word choice in my case study.

    • Caryatis says:

      The real problem isn’t his debt, but his inability to keep a job. Professional jobs are stressful, kids are stressful, and whatever mental health problems he has now are likely to only get worse. I foresee long-term unemployment for this guy.

  26. Laurie says:

    Great for you on the house and job, Olivia, you should be super proud!
    I am 66, married 36 years. My husband is a few years younger and came into the marriage with no concept of frugality or any net worth. I had already bought my first home and set up an ira at 25. I waitressed after college because I made more money than in my 9-5 job. I’ve always been a talented thrifter because it’s enjoyable to me-even though I don’t need to worry about what I purchase, I don’t enjoy buying retail. But to your question, I have to say that my husband would have had a very different life experience if he had married a person comfortable with debt and spending. He would have assumed that is how things went. Instead we focused on paying off the mortgage, putting money away for our kids education and living below our means-without any hardship or lack of experiences. When he lost a job a decade ago, he was able to find another without settling or excess worry. I cannot imagine living with someone who didn’t appreciate the talent and hard work it takes to be self sufficient at your age. Our kids totally get (now they are loan free college grads) how living as we did continues to make happier lives without much sacrifice. I’ve read that financial dissonance is a major issue in many divorces. I could not imagine something I worked so hard to achieve being either compromised or destroyed by someone who didn’t have the same security needs. Btw, I was single a long time when we met and lonely also. I suggest you might access a couples counselor that your benefits may provide before you take the next emotional commitment. It can help immeasurably!

  27. Nick says:

    Great case study perhaps my favorite one yet. Olivia you should be proud of what you have accomplished. However as a 36 yr old male with kids, I work with doctors and almost always I see the other spouse handling more of the child care, etc.. those first few years. It just makes me pause knowing where your boyfriend is at in his education. Your at a great spot financially and really the sky is the limit for what your aspirations are. Keep dreaming big, I’m just not sure he’s the man for you. Best wishes

  28. Rachel S says:

    Wow! You are kicking butt with your savings and retirement and how wonderful to have a home you love in DC. I go there often for work and love it’s vibe and culture! It’s also wonderful that you enjoy your commute to work. It sounds like you are in a good place with your home, community and environment right now. And your retirement is great as well! There are a few things of course to cut out to increase your savings rate- eating out and alcohol for two- although neither are that high , maybe split the difference to increase your savings a bit?

    Regarding the relationship- I read the same exact sentences that Mrs. Frugalwoods pointed out, with the same disdain. Your goals and his goals are not aligned. I do not see this working out well, and I’m afraid you would look back on a life with regret, having giving up so many things for him. You are a frugal sister and are doing amazing, he doesn’t seem like a good fit for your lifestyle and goals. Traveling is hard for a physician ( you could go alone though!- which is nice sometimes), and with his specific set of disabilities you mentioned for his firing, is a new program going to be able to support that? Is he going to be able to function as an MD? I of course don’t know him, and perhaps him being fired was a fluke and a new residency will be a better fit?

    Regarding charging him rent- I would. I actually can’t handle a grown well bodied man not working- but that’s an unpopular opinion. Even if he was delivering pizza or working part time somewhere, he would be contributing to the household. Does it really take 8 months of full-time work to search for a new residency program? Especially since you said you were doing the reading/legal type work for him in the evenings once you worked a full day?

    Regarding the PhD- do it! I’m defending my dissertation in March and I’m so overjoyed. It’s hard. It’s very hard. There is so much to it- but now that I’m (almost) at the end, I’m so proud of myself and look forward to the opportunities. I would imagine a PhD in statistics in a place like DC would be sought after. But it’s stressful, and having a partner that you admitted stresses you out- would not make a good combo.

    Bottom line- you are rocking. You are a woman on a mission and I wish you well.

    • Mary in Maryland says:

      Residents are not fired for trivial matters. In my residency I was often amazed by how hard admin worked to keep people in the program. This firing may be a message that Jacob is not meant to be a doctor. I have counseled residents who left residencies for reasons of mental health, and the expectation that an medical employer will make modifications so that a physician can do the work has limits. Pretty definite limits.
      My relationship experience–a husband who spent like crazy and I wound up with debtors dunning me at the hospital. A partner from a well-to-do family who made $180K per year (1984) but had to borrow from his folks for a down payment for a house. His income sky-rocketed. He called to tell me when I was infatuated with my frugal, self-supporting now husband that Mr well-to-do made 15 times what my husband did. I’ve never looked back. We’re a match.

  29. Courtney says:

    Olivia, I’m writing to you as a wife whose husband had undiagnosed ADHD that was only discovered & treated after I found out he spent um… let’s just say, quite a chunk of change in secret from me. So I know what’ it’s like to have a partner with ADHD! But I will say this — the discovery of the secret spending was a huge WAKE UP CALL to him. He is actively in therapy. He is on medication. We have done a 180 lifestyle change so all the debt is now paid off. He got a higher paying job. He is now actively involved in our finances.

    All this to say, ADHD is real, I get it. But was the firing a WAKEUP call to him? Has he reflected on what behaviors got him fired, and what CHANGES is Jacob making since getting fired?

    I also want to point out my concern that he is 36 years old, and still in an unstable career path. In your honest heart, do you think that he will be able to graduate medical school and become a successful doctor? Or is he just pushing through because of “sunk cost”? I worry he is a “professional student” because he doesn’t want to actually work. Since getting fired, has he looked for alternative employment, if for nothing else but to keep to a schedule and reduce going into further debt? Coffee shop, uber driver, etc?

    If this man is the love of your life than he’s the love of your life, there’s no helping that. But I think myself and others, and most notably, YOU, are starting to see a lot of red flags. You are a 31 year old stable, successful woman. You want a CHILD, not a man-child! You are worthy of love and stability.

    The vision you have for yourself of early retirement, traveling, children, etc are just not compatable with this man in this current state, IMHO.

    Lastly I’ll just say it sounds like you are worried about his financial state more than he is, which is troubling.

    Best of luck to you, Olivia, and thanks for being so transparent and honest. Partners are rarely on the same financial page. But I do believe that if you truly truly loved him enough to spend the REST of your life with him, you would not even be giving this stuff a second thought.

  30. Zoe says:

    Olivia, I commend you for all the great work you’ve done! I would say, it seemed like Jacob haas swayed you toward more of his lifestyle and he can be swayed towards yours. My husband and I have a Thursday meeting over beers and discuss chores we need to complete on the weekend including meal prep for the meals we will be eating at home,
    Laundry, errands and other. We have a non emotional chat. Then we split up the list and each agree to tackle chores by Sunday night.
    Maybe this is something you don’t want to do, but we discussed how if one of us works late, the other will make dinner and have it waiting and do Any required. Hires. The late worker has to give advance notice and may have to do a chore on the weekend to compensate
    It honestly really sounds like you need to put your own life jacket on first before helping others here, and you r been helping Jacob a lot.

    • Olivia says:

      This is a really great strategy. We have started down this path – we created a list of all the chores that need to be done, but we haven’t been able to set aside the time to really agree on who is doing what. When I mention the Frugalwoods set up for chores, we both agree that that’s something we want to emulate, but for someone with ADHD, finding the time and doing the habit formation to make this happen has been hard. I like the idea of discussing over beers each week – maybe just taking it week by week would be a good strategy for us to try instead of trying to create this huge schedule.

      • Michele says:

        Obviously Jacob is highly intelligent, to get as far in college as he has. However, even geniuss can be difficult to live with. He has a master’s degree, and should be able to work somewhere. My ex-boyfriend was never diagnosed with ADHD, although looking back he probably had it, and I made a lot of excuses for him too. No more.

    • Sandra, Italy says:

      Hey Zoe, love th idea of these Thursday meetings! 👍🏽

  31. Wow I’ve been reading these case studies but never commented on them until now.

    Reading this as a complete stranger, it seems to me you really need to think about whether Jacob is really the life partner for you. I noticed you mentioned more negative things about the relationship/him than positive. That’s not good. Other comments already went into more detail about this issue and I don’t really have anything else to say as I’m like a decade younger than you and probably not someone who should give relationship advice haha.

    You’re doing so well financially and in other aspects of your life, I want to be like you when I get to be 31! I definitely think that if you are going to be with someone, you do need to think about their financial situation and whether they’re good with money. I’m not going to ignore that because of my feelings for them. I mean, so many relationships end because of money issues (debt, overspending, etc) so I disagree with Mrs. Frugalwoods on that.

    You seem so confident in your life and where you want it to go, so I think you’ll figure what to do and how you’re going to approach this now. I don’t know if this comment even helped but I just wanted to put in my two cents.

  32. Beth says:

    Olivia- 2 thoughts. 1. Regarding your comment “Jacob and I have excellent communication so I see some hard conversations in our future.” Have the hard conversations now – why wait? 2. Get back to yoga. It’s clearly a passion and outlet that you enjoy. Allowing yourself some “you time” may allow some mental and emotional space to find some more clarity regarding your relationship status and future goals. Thanks for sharing your “case”.

    • Mary in Maryland says:

      Yeah, I was shocked about the idea of having the hard conversations later. Also, you may want to check youtube for the country western song that includes the line “If it don’t come easy, better let it go.”

  33. Crew Dog says:

    I also saw huge red flags in the relationship narrative. Since Jacob is not working, he has time to do household tasks such as grocery shopping and preparing meals. There is no reason he cannot meal prep and help reduce costs rather than increasing them. I see no evidence of teamwork – it sounds like Olivia is doing all the work, and the dynamic is more like a parent/child relationship than a partnership of mature adults. Jacob appears to be a liability, not an asset. Since Olivia already has a good life and well-thought-out future plans, recommend that she make a pro/con list of what Jacob adds/subtracts, and be honest with herself about whether Jacob helps her reach her goals or whether she would be truly happy giving up those goals simply for the sake of a relationship. It does not sound like they want the same things out of life.

    Turning to the PhD discussion, of all potential areas of doctoral study mentioned, Evaluation/Statistics is most likely to have the largest ROI (read Quit Like A Millionaire for a discussion of how to pick a lucrative major/degree) and offer the greatest range of potential jobs. Most of the other options would limit career choices to academia and, as mentioned, staff-type roles rather than faculty positions that would pay more. Why not pick the program with the most future flexibility and highest salary?

    Olivia, you deserve a partner who doubles your joys and halves your burdens. Don’t settle for less.

    • Sarah says:

      Hey, these are all great insights. Just wanted to point out that in DC, there are lots of jobs (in federal agencies, nonprofits, etc.) that use the PhDs Olivia listed, start around $100,000/year, and have staff-type structures (40-hour weeks) rather than academic structures. Signed, someone with such a job who knows lots of people with such PhDs and jobs 🙂

      • Crew Dog says:

        Hey, Sarah, that’s good to know – thanks! I haven’t seen salaries anywhere near that for those degrees in not-DC.

      • Amanda says:

        I’ll second this, and I’m in not-DC. If you’re flexible on location and have good skills, you can get a good staff-type role with a PhD in almost any education field.

  34. Victoria says:

    It was really brave of Olivia to send this in, and brave of Liz to approach it!

    I agree with the points already raised. In talking about a future with Jacob, your language seems to be only about how YOU would have to compromise your goals and values, with nothing from his side.

    I have a disability so I recognise there are things a person may struggle with, but as the others said, Jacob does not appear to be making any of the sacrifices or effort. He has no money and wants to spend money on a trip (six flags) so you pay for it?

    I really commend you for all of your hard work and that really shines through. You have designed a life, location, property, job, hobbies, access to family that you want. And in your case study what you are saying is that ALL of them will have to be reduced in order to stay with Jacob.

    There’s a book called Too Good to Leave, Too Bad to Stay that you may find helpful. Loving someone and feeling happy on one hand, does not outweigh the stress and fear you carry on the other.

    In strictly financial terms, I agree with Liz. Don’t go near Jacob’s debts and prioritise your 20% equity. Really, well done.

  35. Brittany says:

    You’re really impressive! The amount you have saved and the fact that you own your own home at your age and income is awesome. I’m cheering for you. I just have one thing to add- the FWs are clearly on the same page financially, but there are people in the FI movement with a spouse who doesn’t share the same goals that keep finances completely separate. It is hard for me to picture how that works, since like the FWs I married my husband when we were young and broke and we have always been on the same page, but there are people who make it work and seem to have happy relationships. As you consider options, there might be some examples that can help visualize how it might look if you decided to stay together but keep your financial lives separate. Here is an interview with the Mad Fientist’s wife – (Also, like Mrs. FW said, definitely worth talking with a lawyer if you go that route)

    • Olivia says:

      Ohhh yes! I think I remember that one – I should definitely re-listen! Thanks for the reminder!

    • Rebecca says:

      Hi Olivia! First things first, I think you need to take a moment to acknowledge your incredible achievements – creation of emergency savings, retirement savings & a house!!!! Give yourself a victory lap for setting goals and following through BY YOURSELF! I can’t say this enough – you did it! You did it! You did it!! Mrs. FW and many others have given lots of great advise and options to consider. My suggestion is to go somewhere quiet where you can think and reread your request for help/advise. In there is your answer to all the relationship stuff. You went from single to dating to rescue mode. My guess is that you may have already set a foundation of being a permanent rescuer/fixer. Before the relationship goes on further – It is imperative that you consider yourself & your needs, wants and goals first – dive deep. This is not an act of selfishness. Once you come to a decision, the hardest part is the follow through – the sweetest part is the stress relief that comes with the decision and the weight that is lifted off of you as you design your future.

  36. Tigermom says:

    Hi Olivia, could Jacob be in charge of not only paying for groceries, but also meal planning and making lunches? Cooking perhaps? I say this in love-I was single for a long time as well, but met someone who was a great fit in my late thirties and we now have our child. Please guard your heart and finances, when the relationship was right after kissing many frogs, those things became easy. Also guard your energy for your life goals-PhD programs require focus and energy 😉Sending you love and light.

  37. Monica says:

    Right away I think Olivia should think about moving that 23K from a 0.85% interest money market fund to a basic higher interest savings account like Ally where the current interest rate is 1.7%.!!! Will earn her a bit more each month that might add up to a hundred $ a year or so, and it just makes sense! Also, seems like if Olivia gets rid of her PMI (perhaps by using some of he 23K emergency fund?) she would be a candidate for a Home Equity Line of Credit (or maybe even with PMI – I am not sure as I have never had PMI) , which can be a back up for an Emergency Fund fi you are financially responsible. The contributions to her Roth could also be considered for use in a true emergency.

    As far as the relationship with Jacob? I am in the medical field and am concerned that being fired from a residency program (something I have never heard of) is a red flag that Olivia should take very seriously. Only she knows the details and only she can judge how this reflects on Jacob and his future prospects. I am wondering why Jacob is not doing meal prep and lunch if he is not working – which might relieve some household stress? I think a long distance relationship would be useful to see if this relationship will really last, however it might also mask Olivia’s ability to judge what a life with Jacob would truly be like.

    Finally, I am a Single Mom by Choice – my two kids are now teens – so I can support Olivia’s back up plan on having kids on her own. I think she is very well prepared financially at this point- maxing out retirement and owing her own home at her age is great. I think having children a bit later in life was helpful for me because I was well prepared financially and I had had significant success in my career, and Olivia appears to be on this path. One “exercise” I suggest for preparing for children who will likely need daycare is to make sure you are prepared to decrease other costs, most likely contributing to retirement or other savings, once you have children in daycare. I live in Boston, where like DC, daycare costs are outlandish. I just did a quick check and see that my employers daycare (a major Boston hospital) now costs $2400 a month for 5 day a week infant daycare! A toddler is $2000 a month and preschooler is $1700. Also, being close to family when you have children on your own is crucial! There are SMC groups that Olivia can look into if she decides to pursue this path. It is a difficult path, but I would do it again.

    • Olivia says:

      Thanks so much for these comments Monica – it’s good to hear from a single mom by choice. Most people just look at me like I’m crazy, but personally, I think if my own mom can process a divorce with two toddlers, SMC has to be easier than that!

      FWIW – there’s a whole website out there for residency positions that open up, so while it’s not common, I think it happens more than folks think.

  38. Caroline Bowman says:

    Something struck me, and it may simply be wording but why is it EITHER resolving his situation re work and residency program OR getting part time work?

    Some people, Olivia for instance, do a full time job, they complete MA’s and many of those same people have kids (or are carers for parents or other family members).

    I have a son with quite bad ADD (he’s only a kid yet, but still), so I do appreciate that he has barriers to doing things that others may do easily, but if he’s dealing with his medical school situation, then why is she spending her evenings sorting out lawyer emails and so on?

    What precisely is he doing all day? Like, an actual break down. I don’t want to sound nasty or harsh, but if he’s not doing the cooking, not working, what does his day look like? Your day involves 5am starts and what sounds like an awful lot else, whilst trying to progress your own financial goals. He lives in your home and pays for the food / groceries, which is cool… but what else?

    Your financial goals were making slow-but-very-steady progress and then Jacob moved in because of his problems, basically, and now things are very problematic with no end in sight.

    It’s very unbalanced. Very. Like, extremely. You want to add a child or children to the mix in the future, and many of us do, that’s totally great and you sound like you’d be great at being a parent, but where would Jacob fit into this? Would you still be doing all the cooking?

  39. Sam says:

    Olivia, like others will probably say here, I was a financially stable, early-30s, good-job-having person who got involved with a less-financially-stable person, and had children with him, on the promise he offered (gosh it sounds so silly now) that he would seek higher paying employment more commensurate with his skills and credentials. Like your boyfriend, my partner has ADHD, and add anxiety to the list — fast forward TEN years, and though I love our children dearly, and am glad I was able to have them (at the last possible minute — at age 35 and 38!), my partner never found better work, and I am the 90% breadwinner who constantly has to take on side hustles to make the financial ship stable. Everything you’re saying — about him not helping much with household tasks, about you having to help with his legal documents and residency search — sounds very, very familiar. The whole time I read your post about your AMAZING financial planning and self-advocacy (girl, you’re awesome!), I was thinking: RUN. Go have that baby on your own; don’t take on a grown adult with 300K in debt whom you’ll have to care for also. I’m sorry; I can’t believe I’m saying this to someone I don’t know, but you deserve more. Love isn’t stress; it’s relief.

    • Victoria says:

      I already commented but had to come back to agree with Sam! I want to say run too. With love, but, pick you and your future children over mess and stress and heartache.

    • Sandra, Italy says:

      “Love isn’t stress, it’s relief” oh LOVE this and you’re so right!

  40. Megan says:

    Olivia- you are one impressive young woman! My initial thought: there is no doubt searching for Jacob’s next medical residency program is exhausting and time consuming, but there is no reason he can’t have some sort of part time job right now. There are so many flexible jobs out there and little drips and drabs of income do add up! It would help
    him with time management as well! Best wishes to you!

  41. Georgia Burdell says:

    Olivia – Way to go!
    I 100% agree with Mrs. Frugalwoods’ comments on your relationship status. It sounds like you, as an individual, have your sh*t together. But adding Jacob to the mix is basically up-ending all of your plans. Your partner should be a net positive in your life.
    If you do decide to go down the marriage route, I would recommend keeping your finances separate and getting a pre-nup. You have a strong foundation, which you should always be able to return to, in case things don’t work out. That is money that you worked hard for, and it should be yours and yours alone.
    As far as residency, Jacob definitely has to consider moving to different parts of the country. Long distance relationships can work out. I dated my now-husband for 4 years long distance (he was in CA, I was in CO). If you want it to work, it can work. It happens a lot in academia. You just have to commit to flying frequently. Notably, though, living apart will not help you achieve balance in household responsibilities.
    Regarding the PhD (which doesn’t seem to be a huge stressor for you), I would strongly recommend NOT doing it part-time. PhD’s are hard, and usually painful at times, and doing it part-time just prolongs the suffering. As a faculty member, I don’t even accept students that want to do PhD’s part time, because I’ve been on too many thesis committees of part-time students that take 8+ years to defend. For those students, it’s clearly been a cloud hanging over their life for almost a decade.
    Good luck! You sound like a strong, driven person. Don’t settle. You’ve got this.

  42. Tigermom says:

    Ps-are you sure you are not being underpaid? Looking at government codes for similar skill set jobs? I get the sense you undervalue yourself? Love Tigermom

  43. Sam says:

    Hi Olivia! I’m so impressed with all of your hard work – I’m also 31 and am quite envious of how much you have accomplished. I just want to echo similar themes others have raised about the underlying patterns here. I also want to put the disclaimer that I am a psychologist, treat people with ADHD every week, and still struggle with the following issues. My partner has (also long undiagnosed) ADHD and I often find myself wanting to “help” with things (like the unemployment documents you mentioned) because I want what’s best for both of us and, as you put it, I’m good at it. Being better at something than your partner can make it very hard to not do that for them, particularly in a stressful/high-stakes situation. It is extremely challenging to let people whom we care about deeply and want to succeed (for both of our sakes) struggle to make it through a very hard experience when we can just fix it for them. This is especially true when your motivation for him to succeed seems to be stronger than his own from this write-up (though we of course are not in your life and don’t know what his perspective is!). That said, putting him before yourself now will only set that up as a more permanent pattern if you stay together longterm. Having ADHD of course can make things like planning, initiation, and organization harder, but you can still share goals, values, and big-picture plans even if you approach them differently. If your goals are not aligned and you are taking care of many of these logistical aspects with the plan of shepherding him along with you as you just manage it all, it can create significant stress (which it sounds like it already has), resentment, and burnout, even when he brings joy to your life in other ways. This is something that takes two people to change – 1) you need to trust him that he can handle these tasks by himself or ask for help (which does not have to come from you!) if he wants to do them but doesn’t know how to do so independently, and 2) he needs to have the desire to be more independent, trust himself to make these things happen, and actually follow through on them. Again, I know ADHD can make it harder, but ultimately he needs to take responsibility for managing the ADHD (with meds and behavioral therapy and/or coaching, both of which have significant evidence bases for symptom improvement) to get it to a point where it’s not impairing his career and life with you. Many people with ADHD grow up with parents managing these logistics to a later age than is typical precisely because they are difficult for them, but then the individual never gets a chance to try being an independent adult on their own. It is really common to see marriages where there is a significant imbalance in the logistical and emotional burden because these kids grow up into adults who never learned these skills. They can be learned and Jacob may have just never thought about it! Since you have such a strong ability to communicate, I’d certainly recommend having these discussions sooner rather than later. If you are struggling to keep your own priorities in mind when you talk, having these conversations with a family/marriage counselor over a few sessions can take the burden off of you to manage it all and also advocate for your own needs.

    Also, I can’t say that I know a whole lot about medical residencies as opposed to psychology residencies, but I do wonder about the specific reasons for being terminated – as a training program, I’d imagine residents are expected to make (appropriate) mistakes but to learn from them. As a graduate education program, there are also definitely progressive steps in place for smaller infractions that escalate if the concerns are not addressed. If he was terminated for something pretty significant, I wonder whether that suggests that he didn’t appropriately respond to the progressive attempts to help/remedy the situation, and if so whether the ADHD is at the point of impairing his ability to practice medicine in a learning environment, and if that’s not addressed it could make it extremely hard to do so if/when he is working independently. Again, this is for him to manage, not for you, but I think it’s important to look at his overall patterns of behavior and think about what you might be able to expect from your partner in the future so that you can plan your life accordingly.

    Sorry for the novel! I just see these kinds of relationships from both sides pretty often and have a lot of thoughts about them. 🙂 This is a very hard thing you are doing (opening your situation up to the internet!) so I again commend you and wish you lots of happiness and enjoyment in your future, whatever that looks like.

    • Olivia says:

      This is an amazing response – I so appreciate your insights and knowledge about ADHD (and almost like – can you be our counselor? HA!). I agree with a LOT of what you are saying in terms of what has happened in the past. I will say that there’s a lot of unstated things with the firing that make it complicated, but I really do truly believe that a more supportive program wouldn’t have fired him. It really was about being behind on administrative tasks primarily. He asked multiple times for dictation software that never had responses (but he didn’t ask in the “right” way for ADA), they have him failing rotations that the attendings supervising him communicated (in writing) wasn’t their intention and they aren’t sure why he wasn’t given credit for that rotation, etc. It’s a whole mess. ANYWAY. That is done now.

      I really struggle with the being more competent at certain things and just faster. Jacob is a huge time optimist (my phrase). And while he has taken on more responsibility since the finalization of the firing re: making dinner, we tend to eat after I’d prefer to be asleep. And it’s taking a lot out of me to not just be the one to make dinner so I can eat at a reasonable time. But this is what is best and it gives me some time to relax and watch Gilmore Girls at night instead of worrying about dinner. We’re working on it, but it’s slow going. I find it fascinating that no one has assumed that I have control issues and it’s all him, but hey.

      • Jen says:

        I thought I had come up with the phrase ‘time optimist’ to describe my partner! I have to say I am wondering whether he has ADHD now. He is seeing a psych for his anxiety and that has been really helpful but it is important to find the right fit – the first one he saw wasn’t right and didn’t help at all.

      • Sam says:

        I’m so glad this was helpful! Yes, I think it is extremely important to recognize that all relationship issues (including the normal ones that all relationships have) take two to tango. Your own point that you have a desire to control things is huge because it means you’re aware of it and can try to monitor how it affects the ways that you’re interacting with Jacob (and others). For better or for worse, many people who naturally like to be in control end up with people who either don’t or can’t, because it’s much more compatible than being with someone who also wants to be in control, which can potentially lead to constant battles over who’s in charge. I think what’s really tricky is being able to tease apart when you WANT to be in charge versus when you HAVE to be in charge or else it won’t get done (again, I’ll echo my disclaimer here because I also do still struggle with this too!). With dinner, for instance, if you say you’d like to be done eating by 8:00, what is his response? Many people who are time optimists (I love that phrase!) might say “okay, 8:00? Great, I can make dinner in 10 minutes!” – and they really believe that! If that’s a consistent pattern and you want to change it, saying something like, “I want to eat at 8:00 [I’m guessing this is because you wake up at 5!] so that I can get enough sleep, but instead we eat at 9 or 10. It seems like dinner needs to be started earlier so that we can eat on time. Is this something you can do for us? If not, we need to come up with another solution.” People with ADHD have a harder time estimating how long things take and one aspect of behavioral treatment is literally timing how long typical things take over and over and writing it down, so that they start to understand that, despite wishful thinking, roasting a chicken is not a 5 minute game. Many people with ADHD make schedules and use timers/reminders to manage this very difficult task of keeping pace. Making these kinds of experiences concrete and external is a huge part of helping people change their behavior. If you are interested in speaking with a couples therapist, I’d recommend finding one who has experience with ADHD – as I said, these are extremely common issues and you are so not alone (as the other commenters can also attest to!). If Jacob is in therapy or has a psychiatrist, that provider may also be able to help him figure out what to advocate for in terms of ADA accommodations with his job (and then it’s not your job to learn this yourself and teach him!). It sounds like the program was in part responsible for making things more complicated than they need to be but it will be important to think about what accommodations he requires if/when he becomes a licensed physician and how to advocate for those needs.

        I also think another component here is figuring out what you’re willing to compromise on in order to get your larger goals. Can you have quick dinners that might not be as fancy or are boring but that can truly be made in 10-15 minutes (like pasta)? Can the FW strategy of cooking once and then reheating all week work for you guys? Working on relaxing some of your lower priority goals to decrease your overall stress can be hard but very rewarding. Just like you did in your original post with the long term goals, figure out what your goals are day to day, like going to bed at a certain time, and what it will take to achieve them. Then, think about what you can ask for help with – you are entitled to as much support from Jacob as he is from you, even though you are more than capable of doing everything on your own. Just because you can doesn’t mean you have to. Support can be logistical, emotional, physical, etc. You can also say no to some/all of Jacob’s requests (or to the work requests!) if it is leading to you depleting your own resources or sacrificing your own happiness. Like others said, if you’re expected to start working at 5 am, is there a way to have a discussion with your team to reshape that expectation? Is this your own expectation that you set? Your line about being the only person at work who can handle many of the requests suggests that you’re in this position often – the question is whether it’s coming from others or from yourself. If it is coming from you, I’d recommend pushing the time you start working in the AM back by 5 minutes and seeing how you feel. If you can, make these 5 minutes into time for yourself (5 minutes more sleep, or quick yoga?). Once that feels okay, push it another 5, and then rinse and repeat. Over time, you might find 20-30 minutes of extra time for you, and realize that the world will almost certainly keep spinning. Otherwise, it seems like you sleep, work, and then have time to help Jacob with his needs – but maybe don’t have much time set aside for your own self care, especially if you barely have time to eat dinner before bed. The American work culture today can be extremely toxic and makes us all feel like everything is an emergency all the time. Very, very few things are truly emergent, but conscientious, hardworking people like you often end up working themselves into exhaustion to keep up. It’s definitely a battle and can be hard work to unravel these patterns that we find ourselves in, but for your long term happiness and sanity it can be extremely valuable to work on it, whether on your own or with an individual therapist. Just as Jacob needs to manage his own needs, so do you! 🙂

        • EJ says:

          Love this comment!! I think this is helpful for so many of us.

        • Olivia says:

          I definitely missed this response back in December! Thank you SOOO much for taking the time to write all of this! Yes, Jacob does regularly set a timer and this works better for some tasks than for others. (example – remembering to start/stop on dinner isn’t always successful, but just setting a timer to go off every 10-20 minutes while working emails so he knows he needs to move on is pretty effective).

          “I think what’s really tricky is being able to tease apart when you WANT to be in charge versus when you HAVE to be in charge or else it won’t get done” — 1000% THIS!! I struggle immensely with this! Some of it is caring too much about future Olivia (“I don’t want to deal with this later, so it better be done NOW”). This means that I can spend a whole weekend cleaning the house or doing chores or cooking (when I was single) and never seeing my friends or relaxing or going to hike a mountain on the weekend. Jacob is better at living in the moment and reminding me to look up and see the hummingbirds. 🙂

          Some it too is also – how do we define what actually NEEDS to get done? He spent an incredible amount of time transforming my backyard into an amazing oasis that folks walking through the neighborhood regularly comment on. As he was working on it, I was always frustrated that he was doing things outside when there was still so much to be done inside – boxes to unpack, laundry, cooking, etc. But now that the yard is done, I absolutely love taking my morning or afternoon tea there and watching the bees pollinate our (free) flowers and harvesting bell peppers (grown from seed) from the garden. Boxes can be unpacked on rainy and cold days, but yard work has a season. I couldn’t have done everything that he did – felled a tree and dug up the entire root system because it was invasive, poured concrete and built steps… It was an incredible contribution to the investment I’ve already made and I am so thankful he did it willingly and loved every minute of it, as frustrated as it might have made me at the time.

          I have also started seeing my own personal therapist and we haven’t talked about Jacob as much as I would have thought yet. Mostly it’s been about challenges at work and goal setting. (Recently have been backing away from the PhD idea.) Partly because we are only living together part time, but also partly due to the updates I shared, that the COVID work from home life has been great on my mental health and ability to recharge as an introvert.

          Thank you, thank you again for all your time and thought of sharing your comments. I can assure you that they were helpful then and they are also helpful now!

    • Laura says:

      What a thoughtful and informative comment. Thanks Sam for sharing this.

  44. Carla says:

    I don’t think anyone has mentioned this yet…but living on $33k in DC is INCREDIBLY difficult. Metro costs a lot, food costs a lot, everything costs a lot. Living on $33k, diligently managing the budget, and managing to save over $150k and buy a house is an amazing feat. I won’t comment on the relationship aspect but wow. I live in the Maryland suburbs of DC and it would be tough to make it on $33k even out where I live.

    Olivia mentions that she knows she could earn more working elsewhere. Could Olivia perhaps negotiate a raise with her employer?

    • Rachel says:

      $33k is her net take home pay annually. Frugalwoods calculates it based it after taxes, retirement deductions, etc. still impressed by it but it’s not the poverty level wage it would be if that was the total.

  45. DL says:

    As a physician I am seeing big red flags with Jacob. He was able to get a master’s degree, finish medical school and match into a residency with his underlying learning issues but then gets fired from the residency? This doesn’t make sense to me as once you are in a residency program they will do everything they can to help you succeed. It takes a lot for them to kick you out of a program. Even if there isn’t more to the story than what you are hearing from his side, this tells me there is a good chance he won’t be accepted into another program if he couldn’t succeed in this one. He should do everything he can to get accepted to another program, however, this is not a reason for him not to take a job and contribute to your household!! Applying to a new program is NOT a full time job. And if he is not working, he should be doing absolutely everything that needs to be done around the house for you. He isn’t even a doctor yet and he is expecting you to do more than your share of duties. I shudder to think what he would expect of you if he does become a physician, as most non-physician spouses find themselves having to compromise their life and schedules around their spouse. You seem like you have a wonderful life for yourself, goals for yourself, and frankly I think you will have to compromise a lot of yourself if you stay with Jacob. I’m assuming he was in his first year of residency? That is a lot of debt that he has taken on. If he does become a doctor and earns a doctor’s salary he can knock that out in the first 5 years out of residency. (See the White Coat Investor website if he does work as an MD). But if he does not graduate from a residency program that debt will be monstrous and will likely be just as much your problem as his. Sorry to say but I would NOT rush into marriage with this guy and would see how he handles this current huge hurdle. Many people go to medical school and don’t end up working as doctors. Be very aware of any problems such as substance abuse. How he handles this situation for himself and how he treats you will be very telling as to what your potential future life with him will be like.

    • Jackie says:

      Agree 100% – I’m a nurse practitioner and have worked in some of the few settings where GPs can get credentialed (corrections), as well as with residents. Lots of residents start out god awful (it’s part of the learning process; I was an idiot when I started too) but it takes A LOT to actually get kicked out. Most of the GPs who didn’t complete residency I’ve worked with did nice things like not showing up at all for shifts, bringing vodka to work (in a fucking jail!) in their water bottles, swearing at patients, and seeing 3 patients in their 12 hour shift and doing “paperwork” for the rest.

      There’s not a job around in medicine that tolerates more than a residency program tolerates, regardless.

      • Carrie says:

        I am also a physician and agree with the above commenters. I think residency program directors — who would determine if he is accepted into a new program — would be very concerned if he did not have something concrete to show for the year away from residency. If he was unable to handle the work at his prior residency program, he needs to be able to show that something has changed and demonstrate success at something while he is out of residency. He also needs to show that he has a plan to manage his ADHD, and, to the extent possible, his processing deficiency. If I am understanding correctly and he has 290K in debt AND potential payback to NCHS, his potential debt is even more massive with poor prospects for paying it off. This may be completely off, but the fact that he is continuing to work with a lawyer makes me wonder if he is counting on getting reinstated at his prior residency program, which I believe is extremely unlikely.

        • J says:

          How is the lawyer being paid, did we hear? AND, how are the groceries being paid for? Sorry if these were already mentioned…

      • Sophia says:

        DL and Jackie,
        I’m not medical but think you’re spot on. No business wants to go through the hassle and legal ball of twine to fire someone and then search for, vet, hire, and train someone else. My sense is the issue was egregious and doesn’t bode well for finding a new residency option.

        Dearest Olivia,
        You rock! You’re an ultra-stable full fledged adult and, in my best, loving mom voice: don’t be blind; he’s using you.

        Ask him to find alternate housing. A 36 year-old man needs to be able to support himself, whether as a doctor, a janitor, or whatever. If one of my girls had this guy as a live-in partner, I’d direct them to counseling because I wouldn’t be able to talk without screaming, ‘HAVE YOU LOST YOUR MIND?’ after saying ‘hello’.

        I’m 60, and at twice your age, I implore you to please heed the advice provided by this community. You’re killing it financially and don’t need our money advice but listen to the relationship advice: he’s not going to change and you can’t fix him. He’s already become a financial, emotional, and physical drain on your life. You’re too precious for this.

        It’s been about 8 months, right? I won’t be surprised that, if he gets a whiff of you letting him go, that he will propose to you. Please use your smarts to fully create a life where you are social, physically active, and continue to be financially smart.

        Full disclosure: I was married at 31 and had children at 34 and one week before I turned 38. Olivia, it ain’t over ‘til it’s over.

        Also, most health plans include EAP (Employee Assistance Program) counseling sessions that are free and confidential with well credentialed counselors. My company provided 8 sessions/year through EAP. Please consider using this benefit if you have it. I used it twice in my career for very different reasons and found it was life-changing and VERY beneficial.

        Much love and light to you as you mull over this community’s advice.

    • J MD says:

      I’m also a physician and I came here to say the same thing! Being fired from a residency is NOT like being fired from a normal job. Residents have massive protections requiring months of meetings and improvement plans before firing can even be on the table.

      People don’t get fired from residencies for things like mild disorganization or forgetfulness or not being that smart. They get fired for things like not showing up to work (multiple times), disobeying supervisors in ways that directly hurt patients, having extremely poor performance and being completely unwilling to take feedback, violating privacy laws, etc–bad stuff! This is a MUCH bigger red flag than getting fired from a normal job.

      He undoubtedly needs therapy for whatever issues have led him here, but it sounds like if he is still pursuing legal action, that he is likely in denial about the serious nature of the issues that led to his firing.

      Shadowing is not going to help him get a new job. He should consider getting a license and practicing in an urgent care for a year to show that he is capable of practicing medicine without imploding the way he did in residency. If he has any mentors left or any bridges he hasn’t burned, he should be begging them for help and advice. He will never get another residency position without at least someone to vouch for him and help him hear about outside-the-match positions.

      Olivia, my advice for you is to RUN. I believe you that he is a nice person in some ways, but he will shackle your life down with stress, debt, and whatever personal issues led him to be fired.

      • ED MD says:

        Yet another physician here who agrees 100% with the above comment.

        • A doc says:

          Another physician here who agrees with all the above. It is incredibly hard to fire a resident and requires multiple action plans, probation, etc.

      • Absolutely agree! I’m on faculty at a medical school and know first-hand that dismissing a resident is an ordeal for a program, and doesn’t happen without repeated unprofessionalism (e.g. not showing up to rounds, yelling at coworkers or staff) or egregious patient harm. I also review residency applications for my non-competitive specialty in a non-competitive region. This past cycle, we got 600 applications for 7 slots, and interviewed 80. Anyone who has been dismissed from a prior program gets heavily scrutinized and won’t even get an interview offer without clear evidence that they are turning around whatever the issue was in the first place.

        At all the institutions I’ve been at, the dean of graduate medical education has to get involved to dismiss a resident. I’ve worked with several struggling residents and have only seen one fired, for incompetence coupled with unwillingness to learn from their mistakes.

        Administrative reasons, like not completing notes on time, is a documentation hassle and might even be considered a nightmare, but is not grounds for dismissal. There is something he is not telling you, and that in itself is reason enough to run for the hills.

        • Olivia says:

          I’ve included a comment above as well as another in my update. I have since learned the importance of being clear – he was a contract non renewal, not an actual firing. There were still improvement plans (which he met every single aspect of – early, I might add). His program director never met with him once throughout his remediation period. Not one single conversation. He did not ever have a semi-annual performance review during his last year in the program. He met weekly with his Associate Program Director who approved of all aspects of how he was addressing his remediation plan. The APD left the program less than a year after Jacob was not renewed. We were never told the grounds for non-renewal in the face of a fully executed remediation plan.

          I have seen the emails, I was highly, highly involved. There’s nothing he did not tell me. We in fact had to involve the ACGME multiple times because the program was violating standards.

          The program cut the number of resident they admit in half after he left. Their PGY3s were very, VERY concerned about hitting their numbers because the census was so low. In an internal survey, about 20% of current residents said they would recommend the program to a friend. As much as you want to imply that my partner lied to me and must be a much worse human than he is and how I should “RUN”, I would like to imply that that information makes his non-renewal sound very fishy to me… (might, if you have one less resident, be able to pass more patients around to the others and not have the accreditation issues that could be on the horizon?).

          Just because YOU ALL might currently be part of the medical establishment and consider yourselves to be good people does NOT mean that every. single. one. of your peers is an amazing human.

  46. Allie says:

    Hi Olivia!

    Thanks for sharing your story. It is a brave thing to be this transparent and your numbers are quite inspiring for someone who likely graduated into the depths of the recession. The long term effects for our generation will be felt for a long time. I love the thought of you reaching financial independence and then pursuing a PhD with gusto!

    One item that may deserve a bit more planning and its on dedicated savings account – pursuing having children. There are currently some unknowns, but I would hate for money to impact this decision. For this reason having $20-40K set aside in cash could give you some real options.

    For example…

    – Becoming a single mom by choice with a sperm donor can be expensive. IUI plus sperm can easily cost $5k+ if you have no infertility issues. If IUI doesn’t work, then you may need to consider IVF which is closer to $12k/cycle. This is all before the regular costs associated with the pregnancy that will vary based on your insurance.

    – Want to buy yourself some time and freeze eggs? This can run upwards of $15k plus ongoing storage fees.

    – Want to use a known donor? Could be less expensive, but if still using IUI you will incur all his medical expenses to test and freeze the sperm. Plus you may have some legal fees to dissolve his parental rights.

    – Want to adopt? Traditional adoption adoptions can exceed $40k.

    – End up staying with your current partner and trying to get pregnant while he is finishing up education? You likely won’t be able to leave workforce for extended period. That chunk of change would be very helpful for childcare and could reduce the desire to have more “stability” before having children.

    Having kids is such a personal journey, but I think that there is a lack of transparency about what having children (even in the traditional sense) can really cost. This was something that really seemed like a heartfelt desire in your case study and I think that taking power by saving towards whatever form parenthood takes for you would be really great.

    Wishing you well!

    • Rachel S says:

      Another option to add to your list- Adopt from foster care. My husband and I are foster parents and it is so rewarding. It can be hard, but you can go into it with the “adopt” only mindset and only be placed with a child who is up for adoption. I can name at least 10 people from our county alone last year that adopted a child under a year of age, 3 of which were placed with the families at 10 days old. In our state adopting from foster care is free, they get monthly stipends and go to college for free. Again- not for everyone, but another option for those desiring children.

      • EJ says:

        Thank you both for talking about these options. My husband and I are in the beginning stages of going to a fertility specialist and it is so helpful to know what everything costs. We have also considered adoption from foster care and I’m so glad to hear of people who have had positive experiences with that.

  47. Annie says:

    It is brave if you to share your story, Olivia. Two things I thought of immediately when I read it were, what makes a different residency more likely to succeed? Are the underlying problems Jacob has being addressed? I have a child with both things Jacob has and am familiar with their challenges. The second was: I would not live with someone I was this uncertain about. It’s a personal choice; I just wouldn’t forge those ties before I was committed to marriage. It complicates a lot, or it can.
    I too was single a long time — 10 years! — before I met my husband. When it’s right, it is so right. After a year of dating and friendship, I knew and would’ve married him the next day, no qualifications.
    I too saw red flags throughout. Communication is great. But someone once told me, “to know the truth of a situation, ignore everything he says and watch only what he does.” Maybe that applies.
    Hope you don’t mind the honesty. It all may be very different than it seemed from just reading.

  48. Molly says:

    Olivia, wow, you are crushing it! Congrats and keep it up. I agree with a lot of others’ advice above and just wanted to add a perspective of someone a little closer to your situation. I can really relate to how hard it is to envision a long-term future with someone after being single a while – as a proactive and responsible person, like you said, one starts planning for plan B, and it’s hard and scary to make a switch to thinking about a long-term future with someone. I don’t think that means you don’t want it, it can just be a result of having to think about a solo life for so long.

    That said, I do agree with Mrs. FW and others about the fact that it’s worth taking a good look at the relationship dynamic. And quite frankly, your work dynamic, too. It sounds like you’re really responsible and used to putting yourself last to help others. I’m probably projecting here as that was the main struggle of my late 20s/early 30s. This is an awesome time to re-evaluate and make sure you prioritize yourself at least as much as others , and get the relationship on the right foot. Good luck!

  49. Jackie says:

    I would take a good hard look at why Jacob was fired from residency. Is it *really* ADHD, or is it his work? I’m a health care provider myself and I have to say, I’ve only once encountered a GP without a residency who’s been a good colleague, and I’ve worked with lots including several who got kicked out of residency. Medical schools and residencies rarely fire or kick anyone out who isn’t remarkably bad at their job; most of the ones I’ve known who got kicked out did so because they didn’t show up on time to shifts, didn’t complete their work, or whose work was absolutely awful and didn’t improve over time. There’s not a hospital, clinic, or even a jail system around that will tolerate any of those outcomes from their doctors (correctional facilities are one of the few places GPs without boards can work, FYI, though they’re fine places to work if he can hold down a job).

    I highly recommend taking a good hard look at why he got kicked out of residency, again not a particularly easy feat for someone who’s done well enough to get there in the first place, and see if that connects to your relationship with him at all. Is his motivation poor? Does he not take initiative to do things that aren’t necessarily pleasant, like say cooking and cleaning? Do you do a disproportionate amount of house and relationship maintenance compared to him? It sure sounds like you do, based on your story as it’s posted.

    Additionally, if you consider marriage, consider his ability to pay back his own student debt if he’s unable to get back into residency or if he gets fired again. GPs don’t have it particularly easy with regards to job hunting as most hospitals and clinics require boards to practice even as a family doctor, and if he’s getting fired from residency it’s fairly unlikely a facility would tolerate whatever he’s doing to get fired either.

    Just my two cents. As someone who’s had a Jacob in my own life, it’s fun but not viable to be the adult for someone who’s not got their act together long-term. Getting fired from a medical residency should be a huge red flag.

  50. Melissa says:

    I feel the need to say what many have tried to say kindly.
    I believe you have made up your mind about your future and it does not include Jacob. I sense that you are looking for validation of your decision, which I completely understand. You have your life together and a clear vision of what you want from your future. It does not have him in it. Please try not to feel any guilt over what is best for you.

  51. Stephanie says:

    Olivia – I wanted to comment on a few points your case study brought up as food for thought. I am a physician, and I have to say that hearing that Jacob was fired from his residency program leap off the page at me with warning bells, whether he had any debt or not. This is NOT a common occurrence. From the residency program perspective, it is very difficult to replace a resident, so they have to feel that operating a person down is preferable to continuing to train this person. I have experienced a situation where a resident was not performing at the level they should have due to knowledge gaps. There was tremendous effort from the program to help remedy that situation so the resident would succeed. The other reason for firing would be misconduct, and typically that would have to rise to the level of something illegal. I can understand that ADHD would make residency more difficult, but if Jacob made it through the MCAT, med school interviews and applications, Step 1 and 2, all of medical school including clinical rotations, and residency interviews and the match, I have to believe that he is capable of performing at a high level. I obviously don’t know Jacob, and I don’t mean to be overly judgmental. I don’t doubt that he has many wonderful qualities. Since part of your case study was expressing some hesitation about your relationship, I wanted to outline the concerns I would have.

    I also wanted to comment on what you described as “The worst case scenario for my financial life is that Jacob moves to another part of the country to finish his training.” I don’t agree. This would be difficult for you emotionally, certainly. (My husband and I did long distance for 2 years, I can relate.) Based on the financial situation you have described, it doesn’t seem that your financial situation would change much, although your travel budget would likely go to visiting him instead of other vacations. You mentioned that Jacob was part of NHSC. Even in the best case scenario that he is able to secure a new residency position in the DC area, you are in the same situation as you were before he was fired. His commitment to NHSC will require that he work in an underserved (ie rural) area for several years after residency. And unless you plan to move with him, that will necessitate a period of long distance. I would consider how you feel about that. Dealing with long distance is so common in medicine. I know people who have done long distance for as many as 5 years, and it was the right decision for them. And I know others for whom that was not the right decision. It’s a personal choice.

    I wish you well as you navigate your way forward, both in your career and your relationship. I think it is wonderful that you have a job you love and a community that you love and were able to purchase a house young. All the best!

  52. Jmay says:

    Olivia, kudos to you for doing so well, professionally and financially. It sounds like your job is very secure and so is your living situation. I work for a university and truly love what I do too. Keep up the good work.
    As for Jacob, he needs to find a new job and move forward to clean up his debt and become a contributing member of the household. If he had not moved in with you, what would he have done? Who would be paying his expenses and managing his household? In this relationship, you are the “Sugar Mama” who is saving him from more financial woes.
    Jacob needs to work with a counselor who can help him manage his ADHD and processing deficiency, so that he does not have job problems in the future. Since he knows that his diagnosis presents challenges, he can work on how to overcome those challenges.
    If your relationship is strong, than it will survive a long distance work change.
    Continued success to you.

  53. Christine Keefe says:

    Why does Olivia have to be the one doing everything and compromising on everything? One thing that really stood out to me is that Olivia is more stressed and less relaxed with Jacob in her life. That says it all to me anyways. I think Olivia is already planning for her future without Jacob. It’s the emotional stuff that’s hard, but she has a clear head it seems. What does Jacob bring to Olivia’s financial and emotional life…stress it seems. Does she want to live in Vermont, buy an expensive share in a vacation house that Jacob has an emotional attachment to, etc.? Her family is in the area where she lives right now. She seems to love the area. It just seems like Olivia is the one expected to make all the location, financial and emotional compromises.

  54. Tera says:

    Oh Olivia, I had chills reading your case study. Please think long and hard about this relationship. As my mother would say, “he’s not the last helicopter out of Saigon.” If you decide to end the relationship, don’t give up on a true partnership. Perhaps look into a professional matchmaker. It sounds weird, but it’s a thing and it may be a good way to find a like-minded person who is serious about a relationship and children. There is someone out there who will gladly give to you as much as you give to them.

  55. Lorien says:

    I wasn’t going to comment, but I think I may have some useful insights. I’m a physician. As soon as I saw that Jacob had been fired from residency, I was alarmed. You have to be having some serious difficulties to be let go in the middle of residency. Also, I can tell you that being a resident (in general) is a piece of cake compared to real practice. I’m not sure what specialty he was in, which can make a difference. But no matter what your specialty, you have such pressure on you to produce a volume of work, deal with insurance companies, patients, etc. I guess what I’m trying to say is, being realistic, if he has such a hard time in residency he is going to have an even more difficult time finding and keeping a job once he finishes training. If he wants to go into private practice then he needs capital to buy in or start it. He obviously isn’t going to have that. I’m not at all worried about his age; I went to med school after another career (I have a masters in social work) and at 36, that shouldn’t be a factor in any way. I have also been married to men who sort of relied on me financially and emotionally. Some would call it being “unequally yoked”. It isn’t ever easy. I don’t want to be negative, but your patten is already one of great differences. You are a frugal, considering marrying someone who seems to have no problem adding to your financial burdens while not really shouldering his own. I love my current husband, but we are (ok, I am, since I’m the doctor) spending thousands in therapy to work out some of the same kinds of things you are dealing with. AT THE VERY LEAST you should consider keeping your finances separate even if you get married. As someone with training and experience in mental health/counseling, I see major barriers to long term success for you and Jacob, not least because you are so together yourself, and most men can’t deal with a wife being more successful than they are.

  56. Cait says:

    Olivia, I have to chime in on the pessimistic side here. Most of what I want to say has already been said, but seriously, you need to separate your life from him. Even setting aside all of the near term red flags and possibilities, he’s already inflexible enough to insist that if you were to get married and have children, you would need to uproot your life to be near his family? When you already own a home that you can afford in an idyllic-sounding community near your own family?? I would say dump him now, but the “having you read his legal documents at 11pm” of it all makes me suspicious that he would pull some nasty tenant/squatter stuff and make you go through the legal process to evict him. You are in a difficult spot right now, but the way is clear–do the minimum necessary to get him into a new residency program far away, and then break up with him once he moves out. You are still super young for a metro area like DC in terms of partnering and parenting, you have plenty of time for a personal life reset. Unless he is currently contributing to your household in herculean ways that are not apparent from your story, and all of the red flags around his current lack of job are all a big misunderstanding, DTMFA.

    • Jennifer A says:

      Yes, I too am also concerned he will refuse to move out of your home. Perhaps speak to a lawyer first just to have all the information on laws and regulations around this situation. Sounds overly dramatic, but you need support in making (likely the right) decision to have him move out immediately.

  57. Ben says:

    Olivia you have a good head on your shoulders, and a kind heart. Which is why I want to say this gently. If you were my daughter I would tell you to be VERY careful. In fact I would tell you to run. You will be fine, and you will find someone that deserves all the things you bring to the table.

  58. Carol Howitt says:

    Hello, I’m going to keep this short and I make my comment with a heavy heart. It’s clear that Olivia loves Jacob – but please don’t further the relationship on that alone. Five, ten years down the line – being responsible for everything will kill that love – and possibly you too.

  59. Katie says:

    Respectfully- girl, run. If you are not literally over the moon about Jacob, dump him.

    I dated a Jacob. We graduated from the same professional program. I had a job when we graduated, he did not. I let him move in with me and not pay rent. Instead of job hunting for anything, he held out for his “ideal situation” and would play video games all day when I was at work. I broke up with him after several months of dissatisfaction, and told him to move out. Lo and behold, he miraculously finds a job no less than a week later.

    I dated another guy with $200k in debt. He was great, but not all the pieces were there. Division of labor when we were dating wasn’t what I wanted either. The debt wasn’t the sole reason I broke up with him, but when you already have marks against you, sometimes you have to look at the total weight to see if its the right thing.

    You have a great situation, and it sounds like you set yourself up for a very comfortable existence – a good job, a good commute, a house, a small mortgage- you have it all!, and then gave it all up as soon as he entered the picture. You don’t go to yoga anymore? Your family is 20 minutes away but if you stay with Jacob he wants to move to Vermont to be closer to HIS family? None of that sounds like what you want is being considered.

    Marriage, and dating for marriage, is serious business. Who you partner with absolutely affects what your future will look like. I honestly didn’t focus on the financial questions you posed, because most of what you wrote seemed to be focused on your relationship. It’s hard to read tea leaves, but you have to focus on what the future will hold – what do YOU want your life to look like 5, 10 years from now? Do Jacob’s goals and ambitions and abilities align with that vision? From what you wrote, it just doesn’t sound like he’s the right fit for you. There are other people out there who will fit into your vision. Don’t force it or pretend its ok. Listen to your gut.

  60. Danielle says:

    I’m the friend who always tells people to break up with their boyfriends. If it’s an option on the table, it’s a lingering thought in the back of your mind and that’s not something you want to take into marriage. Now that I’m married myself and have seen the process work, you’re either really excited about someone or you’re not. You either love them unconditionally or you don’t. My husband is not as frugal as I am, has debt when I don’t, and is actually currently unemployed! So I feel you. I knew all of this about him before we got married but I was still gaga for him because he brought so much else to the table. He has always found ways to make extra cash, through Uber or contracting work, and has been a solid companion I can count on. We’re working towards being more frugal together as he looks for work and we consider buying a house. But I knew he was my husband the day we met. It doesn’t sound like Olivia is that convinced.

    But, Olivia and I make about the same amount of money and I am not maxing out my retirement contributions and I would like to know how to do this. My employer offers one IRA, which I am giving to, but how do I get the rest of these sorted out?

    • Thomas A Waffle says:

      Danielle – if you are able to contribute more to the retirement vehicles that are available to you, you should do it! First find out what types of accounts your employer offers. An IRA is an individual IRA and you can open up one yourself through many financial institutions (i actually have 4 – 2 traditional and 2 roth through different investment institutions). Your employer might offer a SIMPLE IRA (which is not the same as a traditional IRA) which has a max contribution of $13k and then you can also contribute up to $6k into your own IRA or ROTH IRA. Unfortunately if your employer doesn’t offer a 401k, 403b or 457b you can not take advantage of these – this is a major failing of the US retirement savings system and I think 40% of americans do not have access to these accounts.

      BUT, if you have more money available to save/invest after your expenses and emergency savings you can open an after tax investment brokerage account. Although you will pay tax on the money going into these accounts now, and on the earning in them as they grow, they are taxed differently (and less) than traditional income so it’s still a good way to save money fore retirement.

      I am not a financial consultant but I have been learning all of this on my own as I realized that it is up to me to make sure that I’m taken care of in the future.

    • Cindy Brick says:

      That’s a great question — What is your guy doing to bring in extra cash right now? A part-time job would help him…and help you feel more positive about this. By just having to cover groceries, he’s actually got a sweet deal rentwise. (Just saying.)

      And am I the only one who’s wondering why you’re spending so much on one cat? We have two large dogs who consume roughly a 50-pound sack of dogfood a month. ($19-30, depending on what we’re buying at the moment.) Our older dog, Charley, has hayfever issues during the summer that lessen if we get non-grain dogfood. He also has meds and an annual visit to get those meds. But it’s nowhere near what you’re spending, Olivia…

  61. Jennifer A says:

    No one has mentioned living separately immediately. As a first step you can ask him to get a place of his own immediately (ie not when he is “ready” or has a residency, right NOW). You need space to think and figure out what you want, as well as focus on your yoga and meal prep. He also has much to figure out for himself and that you cannot change for him: financially, with his ADHD, if he can actually get/keep a residency after being fired. I doubt he will step-up TBH but you must get him out of your home at the very least as a first step, if you feel like you are still not sure he is for you (sounds like he is not, but only you can know that). Bravo on all your achievements! You are a rockstar!

    • Rachel S says:

      I agree. And honestly, there is no reason for him to get a job right. He’s got it good- no job, no responsibilities, living in a nice home. He needs to move out yesterday and then see how the relationship progresses.

    • Sean says:

      I agree with this. It sounds like Jacob moved in at an accelerated time frame for the relationship solely due to the circumstances, not because they were ready to combine their lives or become partners at the level of co-habitation. As much of a hassle as it is, they need to undo this mistake to get the space to figure out from dating and then dating-as-long-distance (if Jacob does get another residency) if they want to continue the relationship.

  62. Tiffany says:

    This was a really intriguing study, and I am completely envious of the amount Olivia has already been able to save towards a possible early retirement. I think all the points Mrs. FW made are completely valid.

    I don’t have much on the financial aspect to say, but from a relationship standpoint — I think it’s incredibly important for partners to be on the same page as far as their life goals. I’m not saying that they both have to enjoy water skiing, or collecting porcelain cats, but I mean in the sense of the ‘end game’. There also has to be a mutual respect for each other within these goals and for each other’s strengths & weaknesses. My husband and I recently celebrated 10 years and we both attribute it to those main factors.

    My brother most recently is in an interesting predicament that reminded me of this case — He has always been financially smart with no debt, and purchased a house in his name while dating his at the time girlfriend. His girlfriend recently turned fiance has accumulated a mass amount of student debt over the years, but they will both share that in becoming a partnership. They are placing the debt factor aside, because they are compatible and both want the same end game. By not having a partner who is on the same page can definitely cause issue for life goals, especially if they are financially oriented.

    I think Olivia has a lot to think about. Decisions about relationships are not easy, but you have to assess what is the most important to you? Financial independence & early retirement, or being in a wild whirlwind romance with someone who makes you occasionally feel good, but has an avalanche of debt and problems?

    There’s a lot of great comments on this post! I hope you find the answer that you’re looking for!

  63. Michelle says:

    Olivia you were courageous in sharing such personal issues with us! As so many people have already written, I will add two points: 1- I was sad to read that you converted your yoga room into a storage room since your partner moved in. You love yoga, and you let objects take the place where you used to do yoga? I suggest to take all those objects out, and go back to you personal sacred space in your house.
    2- I am also in a relationship with a man with no money. He is a refugee from Africa and he lost everything when coming to Canada. The difference is we are much older than you (52 and 61). I know that my spouse has a chronic disease and I will eventually have to pay everything for him when he will no longer be able to work. So we will not get married, the financial consequences would be too severe. We did a customary marriage so in front of our friends, family and community we are married, but we signed no paper. He is also ADHD and at times I find it difficult. Regarding expenses, he gives me little money sometimes but he definitely doesn’t pay rent or anything else. Every Friday he buys a good bottle of wine and this makes me happy! I love him for his essence as a human. But I do not take his financial burden. He has 4 kids and I am not supporting them financially.
    I hope my little notes help you.

    • Chelsea says:

      Michelle, you live in Canada, so I’m not sure if this applies, but in the United States there are states where common law marriages exist. Things like living together for a certain period of time and referring to each other as “husband” and “wife” can make you legally married, even if no documents were signed.

      Again, not sure if this is the case where you live. But it may be something you want to look into to be sure. Just so you know how your relationship is viewed from a legal standpoint!

  64. marlies says:

    Hi Olivia, thanks for your case study. And Mrs Frugalwoods for the recommendations. Viewed from my perspective, there is no financial case study here, HAHA, as you’re doing so extremely well! I’m 10 years older and should come to you for advise.

    On the insight on the emotionally supporting an unemployed partner topic and relationship in general: advise doesn’t really count on that, does it? As it really has to do with what feels right. I’m not a relationship therapist of psychologist but even they don’t give advise, but help you gain insight, don’t they?That’s just what you’re asking. So the above just to prevent it sounding as advise.

    Here are some thoughts: Isn’t it extremely scary to loosen the grip you thought you had on your life?! And don’t you hate that uncomfortable feeling?! Maybe I’m completely off, but your story made me think of the time when I had been single for quite a while, and the relationship before that, in hindsight had been too much about liking that he was so nice to me, instead of liking him all that much. I then met my (now) husband. He confessed wanting to be with me and I did want that too, a lot, but was also afraid I couldn’t trust my feelings. I really tried to reason whether my feelings were genuine. And that just doesn’t work for feelings. Me rationalising it all stood in the way quite a bit. Luckily he hung around, I gained trust and we’ve been together for 18 years since.
    And at the moment my career takes a turn I didn’t expect; returning to work after having been seriously ill doesn’t seem to work out. I know I’ll end up somewhere else. Maybe it will be an even better fit. But for now the uncertainty just feels VERY uncomfortable.
    Thirdly you must be a wonderfull planner. Or is it better to say you must have been born with a delayed gratification talent? How else could you be in the place you are at the moment. Financially as well as with al the other plans you made for yourself. All those plans must mean you’re strong on the rational side. Otherwise you wouldn’t have managed all that.

    All the above (some about me, but all in reaction to what you wrote) makes me think: your current situation has all the uncertainty of the unemployment of your boyfriend, there must be discomfort of your former plans not being so solid any more (in case he’s part of your future) together with your presumed liking for influence on your own situation: STRESS!
    At least some….

    You WILL know what’s best. And I think all the comments will help. The ones that resonate most must fit you best. Give yourself some time. And regardless of whether you choose together or alone: I’m sure you’ll end up with very smart financial decisions catered to you’re situation.
    See, no advise! I’wouldn’t know what to advise!
    I am planning to read the two books recommended by mrs Frugalwoods as they sound so interesting. I read “Maybe you should talk to someone” by Lori Gottlieb before and liked that a lot.
    Wishing you the best.

  65. Caryatis says:

    Olivia: if he got fired once, what makes you think the next time will be different? What will your life be like if he never becomes a doctor? Or never gets any kind of stable job?

    Notice the false dichotomy in how you describe your options: Jacob or single parenthood. No. There are other men out there.

  66. Donna says:

    It seems like Olivia mostly has her financial life in order and her real questions are about her relationship and life path. These are the things that went through my mind as I read, which might spark some insight.

    Why isn’t Jacob packing Olivia a lunch to take to work? It just seems really strange that his financial contribution is groceries and that he’s not also taking some of the 40+ hours a week where Olivia is at work to do the meal prep for that while she’s supporting him financially.

    If Olivia decides to get her doctorate, would they try a long distance relationship or break up when Jacob needs to move for work? How long would she be committing to stay at her job for the tuition reimbursement? Would a doctorate actually benefit her career long term?

    If Olivia does move, does her co-op allow her to rent, or does she have to sell?
    Since her usage is on the higher side, it would probably be worth checking into other discount phone carriers that do unlimited talk and text with metered data (republic, mint, Google Fi) if her employer isn’t going to cover it. While it would only save $10-$20 a month, that really adds up.

  67. KN says:

    Oh Olivia. I have dated many a Jacob. Jacob’s not a “bad” guy! But are you really sure he’s doing what he needs to do to succeed? The firing from a residency is beyond red flag.

    ” I had a whole room dedicated to yoga before Jacob moved in, but that room is mostly storage now.” Tell Jacob to get it cleaned out and organized so you can use it again. You say you have cheap yoga classes near you, and also you could consider using free or inexpensive online yoga subscriptions.

    “by the time the weekend rolls around I’m so burnt out I can’t bring myself to spend Sunday meal prepping, which then starts the cycle of spending all over again…” Jacob can learn to prepare basic meal prepping recipes. I get my meals prepped for the week in approx 1 hour. They aren’t fancy but they get the job done. If you are helping him with his legal case he can do this. “but I don’t know how to cook” is a sad excuse for a 30 something. Sorry! And if his excuse is that he can’t do something as basic as meal prep because of his ADHD/processing, then to be frank he needs to recognize that he is not in a place to be a romantic long term partner to another adult.

    People can be good people with character traits that make them bad partners. I highly suspect this is Jacob.

    Like I said, I have dated many a Jacob. At age 35 I ended a 5 year relationship with a Jacob! He didn’t want it to end, because it benefited him to stay in the relationship at my expense. Nice person though, very friendly! Anyways, About 4, 5 months later I met another guy on a dating app of all things. Now we are married and expecting our first and only baby any day now. He will be a stay at home dad who I have absolute, 100% confidence in caring for our child while maintaining a tidy home and preparing meals for us. I am now almost 38. The two of us worked together since day 1 to eliminate debt, we have 0 now, and set our family up for financial success. I certainly didn’t expect at age 35 that I would be getting married for the first time at age 37 and pregnant with a baby right now. The world is large and unpredictable.

    I do want to address your desire to potentially have children as a single person. What are the costs of AI? In your shoes I would focus my future on having children as a single person and figuring out how to do so in an affordable way for you. You are still quite young and could certainly meet a different partner and have children with that person, but it doesn’t hurt to prepare for this future of single parenthood. I know on my salary, which is significantly higher than yours, it would be hard to have a child without a partner to help. Daycare around here is about $1400/month minimum.

  68. Sarah says:

    Oof. This post really hit home for me. I’m in a relationship of about the same length with an underemployed partner dealing with some mental health issues. I also recently bought a house (in July) and am working toward FI.

    To the employment piece. My boyfriend is working for very little pay, but does have several gigs cobbled together. He doesn’t make enough to live on his own, but he does work very very hard. Since I’m the main contributor financially, he does basically all of the cooking and the vast majority of the rest of the yard work, laundry, and house work. I clean up for about an hour every weekend, and that’s it. The financial piece is still hard for me sometimes, just because I do sometimes wish he could treat me or something, but he contributes enough in other ways that it’s not as much of a problem. I do think I can live with this part long term because I love having him in my life and I do feel like he’s an equal partner in those ways.

    The part I struggle with — and what jumped out at me in your letter — is the mental health piece. My boyfriend suffers from some pretty serious and untreated mental health issues, and that affects his ability to work in certain settings and affects him in other ways that make a difference in our relationship. I have had to basically draw a line in the sand that if he doesn’t get help and really work on these issues, we can’t be together. It’s a really painful process (he does seem to be making baby steps at this point). That was a long way to say that I’d encourage you to reflect on whether your boyfriend is taking steps to deal with his ADHD, without you pushing him along and/or doing all the work for him? If there’s a lack of change or effort in that regard on his part, then these issues will keep coming up. I’m not as worried about his med school debt IF he can finish a residency program and hold a job. If he’s not doing the work to deal with his mental health, then this will never happen.

    I definitely don’t have the answers as someone who’s also in the thick of this, but I hope it helps to know someone else commiserates from a corner of the Internet. I wish I lived in DC to suggest a drink sometime!

    • Olivia says:

      Hi Sarah, Thanks so much for these comments! It’s helpful to hear from someone that is in a somewhat similar situation, even if only on the internet. 🙂 I also wish we could grab a beverage! I can’t imagine how hard it must have been for you to put your foot down and draw a line – I don’t think I’m there yet but I am glad it seems that your partner is taking baby steps in the right direction!

    • Lauren says:

      PLEASE have him take the MMPI (Minnesota Multiphasic Personality Inventory). It’s a $500 test at a therapist’s office that could make/ break the future. Any possible future partner I have will take this (on my dime). I will also never marry again without a prenup. Hey Olivia and Sarah – Olivia might not even get to this reply because, holy cow, this is the longest thread I’ve ever seen on a Reader Case Study.

      I’m 37 and just out of a similar scenario, living two hours south of Olivia (Richmond, VA). He was perfect for almost four years and the reason he was out of work sounded rational (and, I’d been laid off during the recession, so I’d been there). The women that have posted GTFO messages on here have clearly been in similar circumstances, and are too far along in their lives to break it delicately. My relationship cost me thousands, five fertile years, and the worst emotional upheaval of my life (saying this as someone who grew up in a cult with abusive parents, got out and put myself through an undergraduate and two masters). Turns out, he has borderline personality disorder, and possibly other clinical issues. Not all MH issues are deal breakers, but someone has to be willing to work on his/her MH on his/her own. I saw someone post on this thread who works in MH say it takes two, and, while social support is always important, anyone working in MH will tell you that someone won’t change until s/he wants to.

  69. Lea says:

    I think Olivia is doing great and wanted to weigh in as a long term single woman who became financially secure (but not FI) and had a child on her own by sperm donation. It was wonderful and the best decision I ever made. Two years ago I bought a house. Shortly after I got in a relationship with a man whose financial philosophies did not match up to my own. Between the “new house” costs and trying to keep up with his spending (weekend trips, frequent meals out, trying to find activities that 4 children of varying ages enjoy) I went into debt for the first time since I was in my 20s. I started by scaling back on meals out and trips and the costly entertainment (those trampoline gyms are fun but costly!). However, I still would watch him max out his HELOC to make home repairs, charge $400 shopping trips to buy things he and his children just didn’t need (no child needs 3 pairs of basketball shoes), and just overall spend as if he found a money well. It was so hard to envision a future with him spending and me saving. He is loving, compassionate, helpful and overall an amazing person but its been hard to fully commit knowing that he is upside down in his house and spends on a whim.

  70. Norm says:

    As to supporting an unemployed spouse, since it has happened to us several times in the past 15 years, I think the best you can do is stop them from falling into that dark hole of depression. There was a satirical cartoon video I can’t find now called “How To Be Depressed” which actually helped us a lot by pointing out the worst behavior (don’t go outside, stay in one room, don’t distract yourself, don’t exercise) I would check in on my wife to keep her on track, “Did you go outside today? Did you listen to a podcast or work on a hobby?”

    But I can tell you that being financially well-off makes the hugest difference. My wife lost her first job just after college, right after I got my job, and we had no cushion. It was extremely stressful. (A year later, I lost mine, the situation was reversed, and was extremely stressful again) It’s that desperation that sets in, the need for cash, the questions about “am I doing the right thing with my life?” My wife lost her job again a few years ago, but since my job paid well, we have rental properties, and a lot saved up, it was no big deal and didn’t affect our daily life at all. She had the space and time to search for the right job.

    The problem as I see it is that this guy is living the second situation, but should be living the first. $280,000 in student debt is no joke. He needs the fire lit and needs to be scrambling for cash. If he starts relying on you this early on, forget it. Someone with that much debt can’t afford to be “not as frugal” as you. I also have a profound disrespect for guys who have their partner take care of their boring life work (cooking meals, making appointments, reading lawyer’s emails) so I get bad vibes from all this. I think you’re doing a great job on your own and you could definitely be on the road to early retirement solo. In the hypothetical ten years, that can still happen if Jacob is taking care of his own expenses and doesn’t mind you quitting while he continues to work, but that looks like a big if.

  71. Dina says:

    What a thought-provoking piece! Olivia, I can’t chime in with any good financial advice and it seems that’s been well covered. I just want to say, regardless of where the relationship goes, take care of YOU. What sent up red flags for me, besides the relationship worries, was the fact that you’re neglecting yoga and self care and giving in to a very demanding job. You’re the only person responsible for answering people’s questions? Is there a way someone else can be trained to help out? Waking up at 5am to start working is completely unsustainable, even if you do love your job. Add to that stress the entire relationship and finance dynamic and you’re headed towards burnout. Please, take ample time to take care of yourself!

    • EJ says:

      Love this comment! I 100% agree.

      At my job, my team has been stressed and overworked. I spoke up and my boss and her boss were totally receptive and excited about the idea I presented to make our workload more manageable (we’re hiring someone part-time). It costs a lot to hire and train someone new and most places of employment would rather accommodate you than have you quit because you are unhappy, especially since it sounds like you are an employee who a lot of people rely on. Be sure to take care of yourself!

      • Olivia says:

        Thank you both! I have done some re-tooling at work (I certainly won’t ever win the argument to hire someone else to support me) to be less stressed. Mostly I have high standards for myself, and after a long break, I finally realized this and stepped back. Just allowing myself to let projects die if I was the only one carrying them was extremely helpful. I still haven’t gone back to yoga as much as I did before, but it’s been slowly happening. I’ll do a couple 4 days a week of yoga until something throws my schedule out of wack and then it will take me 3 weeks to get back to the mat. Sigh. Working on it, but it’s hard.

        • EJ says:

          Good for you!! That is still a lot of progress.

          I am a perfectionist when it comes to my house and I have realized I need to give myself more realistic timelines of getting projects done at home. The realization alone was a huge help.

          I wonder if you could ever argue for an intern? We have had some really great interns at our company. I will say I was able to argue for someone part time because we used to have an additional team member and because I am the person who volunteered to be part time! Our intern will be increasing her hours and they are hoping to hire her to fill my position in the spring when she graduates. If she takes another job, they will hire someone else full time. I am still in talks with HR, but I believe I will have the option to stay at 30 hours to keep my benefits. If something should ever happen and they want me to work less, I would switch to my husband’s benefits. I know this does not apply to you at the moment, but I thought I would share with others to encourage anyone who is unhappy at work to come up with creative solutions and to not be afraid to stand up for yourself. Frugality is what has made this possible!

          • Olivia says:

            Yes! I actually did get 3 undergraduate and 2 graduate interns in the spring. Only one was able to continue with me this fall due to budget cuts though. It’s definitely something I am going to look into bringing back post COVID if I still have my job.

  72. Ellen C. says:

    You are financially awesome. Dump the anchor – sorry to be so blunt. No one should work so hard to fix someone else. While you are focusing on Jacob, other potentially more suitable mates are being ignored.

    • Me says:

      Exactly what I wanted say, was reading through to see if someone else did.

      I am happily single by choice. But when I was Olivia’s age, I was in a relationship that should not have been pursued or invested time in. My friend tried so hard to explain to me at the time, that I could be foregoing a possible good relationship while in I am in that dysfunctional one. But I didn’t/couldn’t allow my heart to see the truth in it. Today I am happy that even though I had not envisioned my life as a single woman (and happily so), my life (trajectory) has treated me well. However the truth remains that while we shy away facing reality of a situation, we are loosing time doing so.

      I hope Olivia take all this advice to heart. You are so awesome, I wish the world had more of you. Take care. Really, take care.

  73. Jana Colgin says:


    I’ve read all the comments thus far and I can’t imagine what it must be like to be you reading all these difficult but well-meaning comments. I just wanted to pop in and say good job! I am rooting for you! I believe in you! I know you’ll make the right decisions! Sending love. <3

    • Olivia says:

      Wow Jane, thank you so much. Really, this is my favorite comment thus far. Sometimes I just want to start typing all the things I didn’t include in the case study, but I’m trying to keep an open mind about the feedback and the conversations in my future. Jacob really is the most amazing human, and we tell each other we are each others “person” – so these have been really hard to hear, but I know that no one knows all the details of our relationship as well as we do, and there’s a lot left unsaid here. Warm wishes to you – thank you so much for your comment.

      • Sandra, Italy says:

        Dear Olivia, yes it’s certainly tough to read certain things about your relationship, I get it. “Sometimes I just want to start typing all the things I didn’t include in the case study”. However, I think it should be noted that we are all reacting to what YOU chose to write about your relationship. How did you expect us to react? To me, it seems we’re all squarely in “team Olivia”, as in “Girl, you deserve so much more!!!” I have also met a few “amazing humans” in my life and I didn’t end up marrying ALL of them – just one 😍

      • Victoria says:

        Something I recognised, that helped lead me to the decision to divorce, is that I found myself describing my partner as “he’s a really lovely man, but…” I had reached a point where the but was always there. And he is a lovely man, and he loved me, and it still wasn’t the right fit. Jacob may be really lovely, and lovely to you. But that doesn’t mean that you have to be the one to ‘fix’ him.

      • JB says:

        Olivia! Okay, I’ll admit that initially I was just as worried as all the other dozens of readers who are worried about you BUT — here’s the thing — maybe they’re misguided. Because based on the responses you’re making, who knows, maybe what you are really looking for is someone to chime in and support your relationship. And maybe this response you wrote above is your intuition talking! “Jacob really is the most amazing human” is the kind of thing that the other respondents had yet to hear. In your case study, there wasn’t a lot of talk of what he brings to your life, just a lot of doubt. There weren’t any sentences that didn’t add a “if we’re still together” disclaimer and even a few mentions of stress, and places where it sounded like he could help you more.

        So *of course* everyone flew to your defense! (And I hope that feels at least a little bit good to hear all those cheers resonating through the internet) But maybe now as you read all the worry and concern, telling you to run, it pushes you reveal the “why” of your relationship. Maybe this is an opportunity to reflect on how he enriches your life alongside him. There must be some wonderful ways in which he does. The beautiful part about you doing this case study is, you can go back to this archive almost as a journal entry and read your words, along with the responses again and again over time as things evolve. It may be that you are feeling yourself defend the relationship because you really do believe in it and if so, that is as much of a wonderful discovery as hearing all the advice that feels contrary to that.

        I hope you are getting the clarity you seek!

  74. Lindsey says:

    I read many, but not all, thoughts here but wanted to chime in with a suggestion and a hooray! 1) Hooray! You are very wise, and well on your way to financial stability/freedom/etc and clearly, finances are important to you (and probably should be a big discussion with a life partner) 2)Encouraging you to have a conversation/plan with Jacob around splitting expenses/duties evenly and create a plan to make it feel 50/50- if he can’t contribute $, then he could contribute in duties. Sometimes duties are worth more than $, sometimes not- that’s a very personal decision (For instance, my husband takes on the vast majority of car “chores” while I do most of the financial “chores”- it works for us). Any partnership (in my opinion) should be evenly balanced, unless there is a major crisis (usually medical, in which health becomes the “chore”). Getting fired would qualify, in my mind, as a temporary crisis, but with a slightly different time frame for recuperation.

  75. Mary Ellen says:

    Olivia, we’re all on your side! Come join us here on “team Olivia.” Unfortunately, it seems that Jacob is on “team Jacob.” I’m glad he’s only been in your home since October, and it is time for him to pack ALL his stuff and move out. Perhaps he needs to go to Vermont and enjoy that property? You can’t rescue him. Period.
    You have so much care and attention to give, please lavish it on yourself. Keep your home, keep your money, keep your current job and awesome colleague, keep your brilliant future, and keep close to your mom and sister and future role as Auntie. You’ll likely feel like you’re rolling in broken glass for a little while, but you will get through, and be clearer and wiser than ever. I promise.

  76. Soggy Suzzi says:

    OK, leaving out the hearts and roses, I’m sorry folks, but this financial mess is seriously important to a woman who appears through her writing to have goals that are achievable. The first thing I would say is don’t even consider getting married until he pays off all those loans. If you live (either now or in the future) in a community property state, the government can, and will, come after your house, your bank accounts, your salary, etc. You will now own this debt. I consider that unacceptable I have a relative who is in a long term not married relationship due to this student loan issue. As time goes by, the interest on the interest keeps increasing.

    And yes, unless he is travelling around the country looking for a new residency situation, he should be doing something to bring in some money. It sounds like he has just skated through life with someone else to fall back on and he is unlikely to change. People don’t really change. What you see is what you are going to deal with. Of course, nobody is perfect, but from personal experience, this tendency was uncorrectable and unacceptable and lead to my leaving (with two kids). He passed away a few years ago (poor) and I am now living a comfortable retirement with two professional well educated daughters. It can be done and you are the right age to do it if you so choose.

    I think the other issue you have to consider is your family being where you now live, and his in Vermont. I think Liz has mentioned how few really good jobs are available in Vermont (they both work from home), but it may be different for a qualified MD. The issue with this scenario is that once a move is made, there is not really an option to go back to where you were. Where is your protection if you move, are not married because the student loans are still around, and you can’t get a comparable job with decent pay? I’m not saying this isn’t doable, but I read into your post that it is an important issue and one that is important to you.

    I have to say that I have very strong feelings (negative) about homeowner’s associations, their fees and their trying to run your life. The amount you are paying monthly is (to me) outrageous and the main problem is that every year the fees will go up and when you go to sell it will take quite a while as in my experience (and local area) nobody wants those fees. If you ever decide to sell, please consider staying away from anything to do with homeowner’s fees. Add up what you are paying now (over $7,000 per year) and you will recognize how far that would go for maintenance on a non homeowner’s association type house. I pay $23 per week for the guy to come and mow and trim the yards, and have a list of college kids to come and weed and plant and move furniture and anything else you need a football player type for when needed. The only thing that is going to cost a lot in a regular house is a new roof. I’ve never bought a house with a roof that needed to be replaced. But other than that, if you’ve ever read any of my posts on previous life stores, I buy low, fix up while living in the house, and eventually sell. This is not really your cup of tea, but a good handyman in your notebook will solve almost everything you need. I’m now at the point where my new old house only needs a pantry (will finish this winter) and that is the last thing on my interior list. All the walls that needed to come down are down, the floors are all changed, cupboards have been moved to expand storage in the kitchen, etc. Next spring I will do the yard (it’s a wreck),

    Whatever you decide, I wish you well. Having been through a different but essentially similar mess, I understand how hard this is for you at this time. With emotions so close to the surface, all I can recommend is do nothing until you can take a more calm approach There is no rush to make a decision.

  77. Leslie says:

    Congratulations Olivia on all your success. You are amazing. I truly mean that. Actually, I’m interested in your housing co-op, which isn’t something I’m familiar with. Can you say what town/community this is in? Sounds like a good deal for DC area.
    Since you were with Jacob when he was in the residency, I wonder whether you noticed his issues or whatever before his dismissal? Other people have pointed out all of the pitfalls and possibilities in this situation. The only thing I want to add is that in the first couple years of a romantic relationship, people often are blinded by love and can’t always reckon with issues dispassionately. You seem a lot more logical that I would have been at that age/situation. Keep up the good work!

  78. Stephanie says:

    Dear Olivia, I think it is wonderful that you have identified that you need support and are reaching out to consider some big issues, the biggest of which is your relationship. I know you care very much about Jacob and want to give your relationship with him full consideration. I didn’t see this recommendation mentioned much above, but I would really recommend working with a skilled counselor through some of these difficult issues, either alone or as a couple. Hands down one of the best investments I have ever ever made in my life was going to counseling. Many counselors accept insurance or your employer may have an EAP with counseling benefits. I think many people can be hesitant to talk to a counselor because they think they have to wait for an emergency, but it can truly benefit anyone facing big life decisions and complicated relationships. I wish you all the best.

    • EJ says:

      Such a great suggestion!! It is hard to figure out if a relationship is right for you, even with all of this advice. I think a counselor is such a great idea and would clarify whether or not you are right for each other long term. And if Jacob won’t go, a counselor just for you could help, Olivia.

  79. RP says:

    As someone who is currently coming to some tough realizations in my own marriage/10-year relationship, I’d strongly advise you to pause and really consider if this is the right relationship for you long-term (and have frank conversations about it, which it sounds like you’re doing). You are obviously a strong, capable, independent woman and right now you might not be too bothered by taking on the responsibilities or “steering the ship” in your relationship because you have for yourself for so long. But in time, being the one in charge of everything may wear you down mentally and emotionally. Nothing worse than ending up feeling like the ‘mom’ to your partner, and it can destroy the romantic aspects of your relationship.
    That’s not to say this is necessarily the wrong relationship! If your guy is willing to step up to the plate and take ownership of his adult responsibilities (not just in words but in action – ie take care of the housework, make himself a financial plan, maybe get a part time job while he’s looking for work, generally take action and make suggestions for his own future)… and is willing to make those changes stick, then maybe he could be a great partner. Personally, I would take any consideration of marriage off the plate until this is sorted.
    You sound like you are excelling financially on your own and have built a life that you enjoy. Make sure you have yourself a partner that you not only love but who also helps you build that life and achieve your goals 🙂

  80. CM says:

    Dear Olivia, what do your friends and family think about Jacob? Ask them for their honest opinion; they might be reluctant to give it but it might help you feel happier about your decision.

    A friend of mine married someone like Jacob straight out of school, she supported him for many years emotionally and finically and he massively disrupted her life in many ways. This man couldn’t stick to things, jobs, plans or I afraid to say people. She hoped they would have children together but I am afraid her Jacob was too selfish for that- as he wanted all her support and attention. After 8 years he left her for another woman.

    He didn’t understand why all her friends no longer wanted to spend time with him. We only tolerated him because we cared for her. My husband and I hugely regret not voicing our concerns 20 years ago when they married but at the time we were young and didn’t have the confidence to meddle in other peoples lives.

    After some time rebuilding her life she meet a really lovely man, who deserves her and they have 2 wonderful children. She is infinitely happier now.

    Talk with someone you trust they will want to help you but might not know how to start the conversation.

  81. Alexa says:

    Hi Olivia!
    Thanks for your willingness to share your financial and emotional situation so openly. I applaud your clear thinking and commitment to your financial goals, home ownership, savings, retirement, etc. Very impressive work!
    I am struck by a few comments you made about differences in focus between you and Jacob. You mention he would need to work in a high-need community, but his desire is to live near his family, possibly buy (into) the family property in Vermont, and live in the Northeast. Where does that leave you and your desire/enjoyment of living near YOUR family?
    Are your goals aligned? He’s not a frugal person. He doesn’t want to retire early. His medical residency could last 3-5 years, maybe more. His debt is now at $290,000. You state you don’t want to have children until BOTH his residency is over AND his debt is below $100,000. Do you want to wait that many more years to start a family? Will he be available to parent a baby and toddler when he is starting out in practice?
    Does he value your career–starting with taking an interest in what goes on day-to-day in your work life? Has he met your colleagues, does he remember what you share about them, does he ask with genuine interest about your day? I ask this because my first husband didn’t care, didn’t retain what I shared, didn’t recognize how much of my identify/sense of self was attached to my work life/environment . I stopped sharing, but that became a great sorrow for me, and isolated us from each other. Not a happy relationship.
    Why has yoga fallen off your daily routine? Is that another compromise point in your relationship? What does Jacob do to relax/stay fit/exercise? Has he also stopped his usual activities because of his unemployment? This is not a push for you to work out together, but rather a comment about using one’s time to support one’s physical and mental health.
    I just got a job after 3 years of unemployment. I was acutely conscious of cutting back in all areas until I had a job again and could pay for my expenses. For part of that time I volunteered in my field: to get more experience, to give myself a sense of contributing to society, to make contacts, to get out of the house part of each day, for my sanity. I don’t know what applying to a medical residency program entails, but if I were an interviewer, one of the questions I would ask is: how have you been occupying yourself while you were waiting to be accepted into a new program? What answer will Jacob be able to give?
    Does his previous residency time (credits?) count when he enters a new program or does he start from the beginning?
    Are his loans compounding interest while he’s waiting to resume his residency? If so, why isn’t he getting a part-time job and paying off the monthly interest at least?
    Would you choose Jacob as a friend if there were no romantic interest between you? Can you rely on him to be there for you when you hit a rough patch? If you become sick (say, flu), would he care for you? That last question is one John Steinbeck asked his adult son who was considering getting married: if there is no intimacy for some time, is this the person you still want to spend time and space with?
    Best wishes!

    • Dina says:

      This comment contains so many great questions to evaluate a relationship. I actually copied and pasted it into an email to myself, for me and all my friends going through rough dating patches. Really really good and thought provoking questions for Olivia.

  82. pauline says:

    I’m amazed you can live on D.C. on your salary and save so much money! You are doing a great job, and you need a partner who is on board with the frugal lifestyle in order to meet your goal of financial independence. It sounds like you want to get more education, and while the fees will be paid will the stipend be enough to live on? Or will you have to keep doing your job at the same time? That’s very stressful, and doesn’t leave much free time in your life. You need a partner/husband who is going in the same direction as you and helping achieve success, and not bogging you down. Maybe this is harsh, but I’ve had freeloaders in my life before, and you need to set down some rules. Just because he does some yard work and house work does not make up for financial burdens he places on you. Can he move out and live somewhere else while he figures out what to do with his life? He folks sound well off, but he IS 36, and I bet they’ve been helping him financially his whole like. Are you prepared to do the same?

  83. Anonymous Physician says:

    Hi Olivia,
    You say Jacob caught your eye because he picked his favorite beer by the price per oz, but you go on to explain how he isn’t actually that frugal. This, along with the fact that he managed to get kicked out of residency, makes me concerned he has alcohol use disorder. Of course I do not know all the details, but usually people are on a probationary program with ample time to correct their behavior prior to getting kicked out of residency. Residency programs want their residents to succeed, it’s not like suddenly there is corporate restructuring and the job is cut. This is a huge red flag to me and I would say cut your losses, you’re only 1.5 yrs in. Plus, as many people before me have said, if he is unemployed and living with you rent free he should be doing ALL the housework. Also, you’re 31 so you probably have 9 more years of fertility. Plenty of time to meet a man who has fewer problems and more similar goals to yours.

    • Michele says:

      As someone who waited until age 37 to have a biological child, I would say you only have 4 fertile years left. Yes, I know women do get pregnant into their 40s, but it is rare (without medical intervention.) I was never able to conceive, which is o.k. My advice is give it 3 years, if you haven’t had a child by then, weigh your options. You have done such a great job, with your finances, home purchase, job, and education: trust your gut. You’re doing awesome.

  84. Sandra says:

    After I read Olivia’s story, I immediately did a web search on doctor’s fired from their medical residencies. Maybe just getting a realistic view from other medical interns who have gone through this and whether they succeeded or not getting back in a program would be helpful in the decision making process. It’s disturbing that you’re providing for another human being but only get groceries in return? Consider the reality that you could be being used. Sorry if this isn’t non-judgemental as the Frugalwoods Blog would like but it’s coming across so loud and clear.

  85. Erin says:

    Olivia, thank you for being so honest! You are doing well in your life! Your house and neighbourhood sound lovely and I hope you stay there for many happy years. I have been there (was singles for ages, now I’m married-which is great, but man, sometimes I miss the single life!). I agree with everyone who said that Jacob being fired is a major red flag, and that’s he’s 36 with so much debt and unemployed. Just wondered if he has considered declaring bankruptcy – I can’t imagine getting out from that kind of debt!
    I’m in Canada so it may be different in Washington, but here you are considered to be common law married after 12 months of living together. Letting a partner live with you rent free can mean that you would have to pay him support if you split after 12 months of living together, since you have an income and he does not. This happened to my now-husband with his previous fiancee; she had a right to 50% of their marital home even though they weren’t married.
    Take care of yourself, my dear! Block off some time for yoga and make that non-negotiable. Put up those boundaries at work and home-it may take awhile for people to get used to them, but they will. It’s not your fault that your job function is not properly staffed. Can’t pour from an empty cup!

  86. Rose says:

    Olivia, if you make it this far in the comments, there are lot of red flags calling out Jacob. Poor guy but I can see the red flags.

    My husband has ADD. He has been fired from jobs due to his forgetfulness and lack of attention. It’s happened more than once and it sucks. However, he was also below 25 and got another job the next day in each time. He is abysmal if it doesn’t interest him and he often has “bad luck” aka forgets things and ends up in a bad situation. It’s happened less and less as he has been able to fine tune his interests and work in a field he loves. I’ve made more money than him for most of our careers. Last year, he started his own business and for the first time in ten years, he’s making more money. He has a lot of debt for this business but he has the drive and determination to do it. He is one of the few people I know who loves their jobs and he looks forward to coming back from vacation to go to work. He takes medication for his ADD but he really did the work to make work “work” for him. He learned all of this on his own with little support from his family (and ok a lot of support from me) but he learned how to make it work.

    That being said, I do a lot of the “life” organization, household management, etc. We have a daughter and he is very hands on with her but I need to do the “remembering” pieces for him. He does a lot of the home and automotive maintenance. He does yard work but it’s winter most of the time where we live and the yard doesn’t need that much work. We could benefit from a Mr and Mrs FW division of labor conversation but I would be truly lost without him. He is the love of my life and if I think about the next 10 years without him, my main goal would be to find someone I love just as much. My retirement, my day to day, etc, mean very little without him. I rarely wax poetic and I have to tell him what to buy me for my birthday but damn I love him. Does Jacob make you feel that way?

    • Rose says:

      Also my poor husband has no idea what meal prep is. I make my daughter and his lunch most days. 😛 I get resentful from time to time but I have no idea how to change the oil in my car or any desire to shovel my driveway. He’s still worth it.

      • Olivia says:

        Thank you so much for these comments Rose! I hear you loud and clear. Jacob for SURE does all of the yard work (alas, it’s now winter) and while he doesn’t do all the car stuff, he does do all the bike stuff (there is, admittedly, less bike stuff than car stuff to do). I so identify with your “life” v. “remembering” comments. He is much better at maintaining friendships than me, reaching out and getting to know the neighbors, and desperately misses his patients (who we hear from the nurses desperately miss him). Jacob most certainly makes my life incredibly better and I love him to bits. Thank you for commenting!

        • Diana says:

          Hi Olivia,
          I imagine it’s not pleasant reading all this seemingly negative feedback regarding Jacob and your relationship. I have no doubt from all you’ve shared that you do feel a lot of positive, loving feelings for him and there are many ways that you feel being with him has made your life better. But, your honest sharing also reveals what I believe is your deeper truth: that you already have at the very least serious misgivings about both him and the relationship going forward. At age 62, I can tell you from a lot of extremely difficult personal experience and subsequent growth and learning (the hard way!), you can absolutely trust what your gut is telling you. But it can be very hard to let go of the “happy relationship story” you may be holding on to in your conscience mind. I get it: you want it to work out! But be aware of yourself making excuses for him, justifying his behaviors (to both yourself and others. Spending too much time defending him, “helping” and caretaking him. Doing for him what-especially at age 36!!- he needs to be doing for himself. I agree completely with what so many others here have said so well: there are not just a few, but MANY red flags in this relationship; he is taking advantage of your kind and giving nature and…you are allowing it, to your own detriment. You are giving yourself up in order to be with this person and he seems to be okay with that. The yoga room abandoned to store HIS stuff. The money expenditures you’re not really comfortable with but you go along with because he somehow isn’t capable of cooking/meal prepping? You are too young and have too much going for you to allow yourself to be drug down by anyone! Take it from experience: Takers rarely if ever change into givers; it’s not impossible but highly unlikely. If he’s really as wonderful as you say, he can move out, get a job to support himself and you can reevaluate the relationship from there. You don’t have to be living together to be together!
          I truly wish you all the best going forward in your life!

  87. Laura says:

    Since so many have already responded about Olivia’s relationship, I’d like to offer a thought about the narrow topic of Olivia potentially working on a PhD and the timing of pregnancy (if that’s how she wants to become a mother), whether she does that alone or with a partner. I, too, work for a university (as an adjunct) and I love to learn. I’ve thought about working on a (reimbursable) degree at my institution for fun – and possibly to improve my work prospects in the future. I have 3 grad degrees already, including a PhD from another school, and I’d recommend that she stay at her institution for her PhD, continue working full time there, and do her local PhD part time for free. Once the first couple years of coursework is done, most people struggle “to just get through it” with their dissertations anyway, even if they’re full time students working only part time to support themselves as research or teaching assistants OR at some other job. So, I think she’d feel like she’s “just getting through” her degree way no matter where she goes or how she does it. Might as well keep making money and remove the stress of commuting to another campus farther away. A PhD program could be a nice distraction and might provide a new social circle if Olivia and Jacob part ways, too. Finally, I want to offer a thought about the timing of school and a potential pregnancy: I had my first and only child at 31, the very day I completed my comp exams before moving into the dissertation proposal phase of my PhD program. My faculty advisors encouraged and supported my new-mom status in really helpful and generous ways, though I’m sure it led to the (expensive and stressful) extending of my dissertation deadlines. All that stress led to my husband insisting that we wait until I was done with my PhD before we tried for our second child, and by then – at age 36-38 – I started to have fertility issues related to age and we ultimately haven’t been able to have more kids. All this to say that timing is important. And while at 31, you don’t have to rush into a relationship/marriage to partner up with a biological dad for your child, if that’s what you end up prioritizing, you *are* realistically on a fertility timeline. Thus, keeping your full time job and doing a part time, free PhD could make it easier to withdraw from a PhD program with no financial repercussions if pregnancy/fertility/family responsibilities start to compete with your academic work at that point.

    • Olivia says:

      Thanks for these comments Laura! I totally hear you. Within the last year, I learned about the dissertation format that one faculty member described as “stapling 5 or 6 papers together and calling it a day” – and I think if I were to go part time I would prioritize a program that allowed this format. It sounds like it would be much more manageable to rather than slogging through the minute details of a traditional dissertation while also being more easy to “double-dip” between my job and the dissertation. I do worry about the pregnancy aspects and I haven;t quite figured that out, but, I have some time! Likely looking at applying next fall when we are on the other side of this Jacob employment crisis (and also a massive leadership change in my own job).

  88. Kate says:

    Olivia, all I can say is that you are AWESOME. I think you know what to do about Jacob. A couple of sessions with a therapist will help you to sort out your thinking. In the meantime, you’ll both be in my thoughts & prayers.

  89. Samantha says:

    As I read Olivia’s story, I saw so many similarities between hers and mine. I’ve learned a few things along the way, so I will lovingly share:

    1. By the time I was Olivia’s age, I was in a similar financial situation. I had worked very hard to climb out of debt and save money for a down payment for a house, all while trying to balance funding my retirement. I wasn’t yet married and had been single for years. Like Olivia, I bought my first house with my needs/wants in mind, because I didn’t yet have a partner or spouse.

    2. When I met my future husband, I was debt-free and actively working on improving my overall financial health (i.e. saving for a down payment, saving for retirement, etc.). He was in a low-paying job at the time and had a lot of debt. However, his debt never once gave me pause because of a few characteristics: he lived within his means on a daily basis and he was actively working to pay off his debt, all while trying to get a better paying job. We talked a lot about our values, goals, and personal finance goals before we got engaged or married. We did premarital counseling prior to getting married and it solidified we were on the same page about the “biggies”: money, in-laws, children, and long-term goals. I would highly recommend anyone considering getting married to take part in premarital counseling because a good counselor will help each person to see their blind spots. My partner and I work really hard at communicating well with each other (and still do) and it’s made such a big difference in our marriage.

    3. Prior to meeting my husband, I dated someone for years who I thought I would end up marrying. In short, we did not communicate well. We were on completely different pages about money, children, career, etc. Although we never lived together, I helped support him for years (emotionally and otherwise). A few months before we split up, he was fired from his job. For months, he did very little to improve his situation. He relied on his parents and me to help him out financially. Honestly, the writing was on the wall for me and it became very clear to me one day that we just weren’t on the same page in many aspects. I broke up with him as kindly as I could – he didn’t take it well. Years later, he ended up marrying a woman with a great paying job. She is okay with him doing very little in the relationship. They don’t have any children together, but she has two older kids, who is good to. He was really looking for someone to “parent” and support him financially, and I didn’t want to play that role, but props to him for finding someone who was willing to play that role. It seems to be working for him and they are happy together.

    I wish you the very best of luck, Olivia. Don’t be afraid to take a hard look at your situation and decide if it works for you long-term.

    • Samantha says:

      As a “happy ending,” my husband and I are doing very well, financially and otherwise. He paid off the majority of his debt before we got married, and paid off the rest of it within months of us getting married. We are currently debt-free and plan to retire by the time we are 50 years old.

  90. Emily says:

    Hi Olivia!

    No sage advice, just jumping on to say that given your description, I’m virtually certain we used to live in that community (on Ridge Rd). We live in Takoma Park now but have fond memories. Good luck to you!!!

    • Olivia says:

      Whoa! I used to live in Takoma Park and currently live on Ridge! haha The neighborhoods do have their similarities! Thanks for the well wishes!

      • Paula says:

        Olivia, when I first read your story, I thought “Greenbelt.” I used to live in Cheverly and worked out/swam at the gym/pool in Greenbelt. Best!

  91. Jecca says:

    “I’m much less relaxed and much more stressed with him in my life, but I also laugh more and am more social, healthier, and happier…”
    Which side of the coin is worth more to you?

    • Olivia says:

      For sure the laughter. I can’t say I was more stressed before the crisis situation erupted… But I was incredibly bored and lonely. …I’m also more stressed with my parents in my life but I certainly don’t want them to go anywhere for quite some time…

  92. Cindy in South says:

    Do I dare say this, it is painful. I used to be a domestic relations lawyer (divorce was my primary practice) and I am now a prosecutor. Finances cause lots of stress in marriages, and I have seen it in my former divorce practice, and, unfortunately, as a prosecutor, I have seen people snap. I am also divorced, from a brilliant, yet financially irresponsible man who was also ADHD, bipolar, etc. You are young. You are smart. You are financially savvy. You have your life before you. I had my children with this charming, but very flawed man (I am very flawed also) the marriage was a complete financial disaster and I still have not recovered from it. I don’t want to be a wet rag, but it has stressed me to the max and I am sure taken years off my life. I don’t want the same to happen to you. I would recommend having your boyfriend get his own place, and once he gets another job, then y’all explore whether your relationship can continue. I totally understand being lonely because that is how I ended up in my marriage. I understand about the biological clock ticking. I, because I am also 60, totally understand the ramifications of being married to someone irresponsible. Brilliant folks can talk a good talk, but until they actually show significant walking the walk, I would have him move out, get some space and see if he significantly improves. He should be the one dealing with the lawyer, packing your lunch, coming up with a game plan for his debt, and a job, etc. If he does make significant improvement then by all means, explore the relationship. But, I am very sorry to say, it appears he is just talking a good game at the moment. I hope this doesn’t sound terrible, but I don’t want someone as awesome as you appear to be to get pulled down. Money is not everything, but that type of debt, coupled with no job, is a bad sign.

  93. Anne Feary says:

    Kudos for getting yourself into a (currently) very sound financial situation. It sounds that you attained this solid situation prior-to-Jacob and without much external assistance. Even if you don’t get married, Jacob at this point, is a financial and physical and mental health liability (no yoga, spending has increased, and stress level is higher). Do not allow yourself to become a statistic in the “supported my boyfriend and now I’m broke” category. Regardless, he should be working, at something, besides getting into his next residency program. He should be picking up more household chores. Let him get legal advice from a lawyer, not you. You are not a lawyer. You need legal advice to ensure that he does not a some point claim part ownership of your home for any of his monetary or work contributions made to the household.
    Take commenters advice and learn about codependency and enabling. You appear to be a giver and Jacob appears to be a taker. Jacob will manage. He got through a BS, MS, and med school. One of the best things you can do, for him and you, is not participate in keeping him a little boy.

  94. Deezee says:

    My intent is to write you the best of what I can give in a short summary, because reading your story makes me want to take you to coffee, listen and ask you questions that only you can answer to yourself I read your follow up comments- if you feel grief that you’re letting the FIRE dream die that should give you pause. You are getting a lot of input on your relationship, mostly because your finances are fantastic, there is not much to improve there. But, being that we are on a financial advice column here is mine- put your IRA money to paying down your house. Pay down your house as if it were a 15 year loan for as long as you can (that IRA money will cover that), early money will save you a ton, and bring down your early retirement needs. Based on needing $32k/year you need $800k to “retire.” Adding $45k to that yearly you should be ready to retire in 15 years. I would make a general plan, live for the next 3-5 years and re-asses. Everything will change once you have a baby; goals, finances, ect. Ok, for the personal, I highly advise you to read this advice column. I have it saved to my desktop and re-read it every time I feel lost. I see a lot of ships competing for your companionship. Several you mention seem to be someone elses’ ship, a ship that doesnt make you want to stare at them, touch them, wonder where they go- like the doors you shared in this post. (I too love, love doors like that. Many of my travel pictures are of doors). You are very happy with the life you’ve built, and honestly it sounds freaking fantastic. I want to be apart of it, I’m sure Jacob does too, and so do a lot of ppl! Do not confuse that with being meant to be on that ship. What ship MUST you be on, what journey is calling to your heart like a quiet siren, not an sum of equations. Your heart is calling you, screaming at you and bleeding out to finance blogs to tell you what ship it needs to be on.

    • Triton says:

      Deezee, this link is Incredible. Incredible! Everyone who hasn’t read it, go read it immediately, it’s not long. I may have to save it to the desktop myself. Thank you for a wonderful new resource I had never heard of before.

  95. B says:

    Not to beat a dead horse, but I’m also a physician, and I want to add my two cents so you don’t think the comments above from physicians are just a couple of one-offs. The fact that Jacob was fired from his residency program is a MASSIVE red flag. Residency is not like any other job; they take terminating a resident extremely seriously, and it’s always the very last resort after the resident is given chance after chance after chance and all the resources in the world to improve. Maybe Jacob really is telling you the whole story, but it’s quite possible he’s not. I’m not buying the ADHD thing since he was already able to get into/through college and med school. If you know any of his co-residents, they might be able to shed some light on what actually happened.

    If he wasn’t willing/able to change enough to save his job, for which he’s already spent years in school and hundreds of thousands in debt, not to mention the fact that most physicians see it as a passion or a calling or something along those lines… I don’t see much promise for him being willing/able to change to improve a relationship that probably already seems just fine in his eyes, given that you’re doing all the heavy lifting.

    I’m sorry to be so blunt, but I’ve had times in my life when I wish someone had been more blunt with me. I’ve enjoyed and learned something from every relationship I’ve been in, but I sure did waste a lot of time before I met my husband!

  96. Mrs. Gardener says:

    Hello Olivia,

    Don’t marry Jacob; you are in a parent/child relationship.
    It will not get better because it is fundamentally flawed.

    Mrs. Gardener

  97. Becca MD says:

    Coming from a physician’s point of view, it is pretty normal these days to have the type of debt that Jacob currently has. Residency is also one of the most emotionally tough points a doctor will have in their lives. After all, if you end up taking care of someone’s family member that passes away a couple of times a day…including children… which is not abnormal… is pretty likely you may end up not being frugal with your restaurant decision at the end of the day. To add to this, financial advisors for physicians in medical school are horrible! They tell everyone not to worry about their debt. In the end, physicians have a ton of debt at the end of their career after they crawl out of a horrible residency and are just happy to survive. Sometimes they could have been better with finances and sometimes they just need to survive. Being a physician is like no other job.

    But there is light at the end of the tunnel. Residency is horrible and unfortunately….it will affect the physician and every one of their family members. There are statistics that half of marriages fail in some programs…..that is from people that are already married prior to the program.

    In the end, things will be what they may be but I wouldn’t stress about Jacob’s finances but more his decisions. If he finds a local residency and you can pursue a relationship then great. If it is a long distance relationship…then good luck. Some people do well in this situation. To be honest, he still has a MD and that is a doctorate degree which comes with loans but also multiple options for employment in the future that are high paying. He will learn how to eventually manage his finances…..hopefully. I know it took me a while. I am almost 40 with a plan to pay off my loans in 4 months but have bought a house and had two kids in the past 5 years with a backyard wedding. I actually met my husband during residency but only started dating after my residency was over which really improved chances of a relationship working out. Hope this is not a negative post but maybe some feedback from the other side.

  98. Shely says:

    Hi Olivia
    I agree with Mrs. Frugalwoods on seeing a lot of warning signs in the relationship with Jacob.
    It sounds that you are rather ambivalent about your future together.
    I was impressed with the stress you wrote about with the PMI & the need to fix the situation ASAP.
    As I believe I am somewhat like you, frugal and tend to stress on money issues, I think on how an unimaginable debt of 290,000$ would make me feel. And how much stress it would bring to my life.
    I am very lucky that My husband and I are both frugal.
    However if the “not so frugal “ tendencies of a partner were the only issue, I would think that a great love can sometimes overcome the differences.
    But You write about A LOT of issues with your partner that seems rather problematic : the debt, the assymetry of the workload, his job situation, the ADHD , and I am not sure that there is a connection strong enough to balance all of it.
    To me it looks like that you do not get enough of this relationship.
    Well done on all the hard work you put into your life.
    Good luck

  99. Svet says:

    Nice case study! If I’m allowed to add, my comment is about how finances affect relationships. Me and my husband a happy married for 15 years, I was 30 and he was 35 when we got married. We were lucky to meet each other since beside romantic affection for each other we had similar life goals, altitudes, and financial philosophy. We had huge differences in net worth, but are financial personally are perfectly aligned so we never argue or disapprove each other money decisions. All our spending and saving decisions are effectively joint decisions. Thanks to this fact, we are well on track to achieve our financial goals. I thought it’s the way it always is for all couples. Apparently not. I see a lot of people in long term marriages whim we know very well of our age plus or minus, going through unbelievably nasty divorces. Which kids, joint assets, family/matrimonial home sales, spousal and child support, debt, joint debt, etc. and fighting over all of that in courts for year/years. If you dig down to the main root of why a seemingly perfect family falls apart, it’s mainly about money: who makes or not makes what, who spends and borrows, how much and on what it’s all spent. Advice: look for a partner who’s goals and money personality close to yours. Definitely not the opposite.

  100. Melissa says:

    Hi Olivia, Honestly reading your case study really reminded me of myself and my relationship with my last partner (we are no longer together). I had a lot of similar concerns about his debt and general approach to finances. I too even thought of reaching out to the Frugalwoods nation for input. And I think a lot of great advice has already been given by Mrs. FW and in the comments, so I don’t want to be repetitive. I just wanted to recommend you consider seeing a therapist, counselor, etc. and talk through the situation with them. Throughout my relationship and afterwards, I was going consistently to therapy (I had been seeing a therapist long before I met him for my anxiety) and it was really helpful. I was able to process the relationship and learn more about myself too. I realized that I was focusing on the financial differences as they were easy to see on the surface, but actually there was a lot more going on underneath that had nothing to do with finances. And ultimately our breakup was due to these other underlying issues. As I look back, I can see that it was easier for me to process/think through finances instead of other issues because they felt more concrete and even solvable (you can make a plan for paying down debt, building your finances, etc.). Now this isn’t to say that financial issues aren’t real issues (they are!) or that your relationship has other underlying issues (it may not), but I think it’s possible that the financial implications are just the tip of the iceberg. Further introspection of yourself and your relationship could be helpful as you think about what you want for your future. Anyways that’s just my two cents. Wishing you well and congrats on being in such amazing financial shape!

  101. Olivia, check your Ph.D. program options again if you want to follow Jacob to a high-need area to pay his loans off. That’s where I live and it isn’t a hotbed of convenience, coops or higher education. You are in a sort of quality control position from the looks of it; maybe research up what QI directors in human services or other not-for-profits needs for QI managers in terms of education. That way you have a ghost of a chance to live with your practicing physician honey (who won’t be making downtown money, by the way).
    Or prepare to live where you can work and commute to see him till he’s paid off.
    Look again at how important Jacob the man is to you, and how you live with him now.
    Congratulations on how well you manage money! I wish I’d been as smart as you are when I was your age! And best of luck in your future life.

  102. Ashley says:

    Run! Run for the hills!

    What I actually mean is that you need to kick Jacob TO THE CURB. Sorry to be harsh, but you need a wake-up call and apparently all the red flags you cite in your case study aren’t sounding the alarm. Girl, you got it going on. You are an educated, hard-working, financially-sound, city-dwelling young woman. Get out there and find a good man!!! No excuses.

    I say this with love and decades of witnessing my dad’s repugnant treatment of woman, financially. My dad started (~30 years old) in a similar spot to where Jacob finds himself right now, hundreds of thousands of dollars in debt, failed business/career, and working on not working. My dad has never owned a home (his credit is too bad), instead he moves in with women who own their own home and guess what ??? he pays for groceries sometimes, but doesn’t cook or clean. And then guess what ??? years later he ghosts and leaves behind a financial mess. I am going to echo Soggy Suzzi here, “people don’t really change” and Jacob, unfortunately, is showing you his true colors. At 36-years-old, it’s great that he’s perfected the art of communicating, but until you see action, do not buy into his fantasy.

    My warning is brutal, but if Jacob is “the one,” please, please, please, get a prenup. You’ve worked too hard. You deserve to put yourself first.

  103. Jen says:

    Solely regarding PMI – over the last few years we put a little additional money toward our mortgage principal to try to get rid of PMI sooner, but in the end the mortgage company would’ve required us to get an appraisal to be sure we actually had paid 20% of the current value, and the cost for the appraisal wasn’t worth the few more months of $35 payments so I left it on and let it expire on its own. I can’t remember what the cost of the appraisal would’ve been, but when I added up that I had around $200 of PMI left, it wasn’t worth the hassle. You should check the cost of an appraisal versus how many months of PMI you have left to see if that is worth pursuing.

    • Olivia says:

      Thanks Jen! That’s an excellent point. Mine is $37/mo, so I can imagine being in a similar boat.

      • Anne says:

        If your PMI is only $37/month, mathematically you may be better off not paying down early to get rid of it. $440/$12987=3.4% return you are getting on that money by eliminating PMI (plus you will ultimately be paying less at the end of your mortgage by paying early), vs an average 7% return in the stock market. It doesn’t make a huge difference unless it allows you to refinance to a lower interest rate. So DEFINITELY don’t beat yourself up over it! And think seriously about whether that makes sense right now or if you have other goals you want to focus on instead.

  104. Kim says:

    I want to share with Olivia that I am in a position where I financially support my husband due to a serious chronic illness. However, even with the physical pain he has to deal with every day, he makes my lunches and dinner, is the main caretaker of our pets, drives me around if needed due to the fact that we share one car, does the grocery shopping, and so on. A marriage or partnership can work different ways for different people, but I think working together toward goals as a team is kind of a necessity. Wishing you good luck in finding your way!

  105. Turia says:

    Hi Olivia,

    I’m not sure I have anything new to say after reading the comments but I wanted to at least add my congratulations for all your hard work and what you’ve achieved this far. You’re amazing. Really.

    I would take the comments on here from doctors about the red flag of being fired from a residency program very seriously. How is Jacob handling this? Has he acknowledged the fault he carries? Has he made a concrete plan to deal with the issues so the same thing does not happen again?

    Why is it that in your portrayal of your future life together it is always you who are making the compromises? That really stood out for me- that Jacob wants to live near his family (but what about yours?) and he wants to buy in to the property. You say you have great communication but then your friend asks if anything changes.

    I don’t know if anyone has asked this yet so I will just say it- is Jacob depressed? Is that why you seem to be carrying everything- the work, the cooking, his problems, etc.? That’s the only acceptable reason I can think of for why he’s not taking over all the household things he can, especially if you’re also managing the emails and emotions from his job loss. If he is depressed, is he seeking help so he can get better?

    A PhD is not remotely comparable to a MA. I don’t know your field but I know many people who tried to do one part-time while working full-time and it really became a millstone around their neck. I would advise you to talk to people in your proposed field (many people) before you take the plunge. See if it really will be worth the time investment.

    Lastly, please don’t listen to people who say you have nine years left to have a child. For a small percentage of the population that’s true. But I wouldn’t recommend waiting much past 35.

    You are clearly a strong, focused woman and I am certain you can achieve anything you want. Good luck figuring it all out!

  106. Mable says:

    Debts can be paid off; personality does not change. Second, you are living in an unequitable situation now and things tend to get cemented over time, not improve that much. All I have to work from is my personal experience: when my husband was laid off, he took over 100% of the house duties, without ever being asked. He also saw it as part of his job to cut expenses to the bone until he was employed again, so he cooked frugal but healthy meals, always had a lunch packed for me plus a mug of hot coffee to see me on the road to work. Until he was re-employed about five months later, I never filled the gas tank of the vehicle, ran an errand or went grocery shopping. When he went back to work, I was a little disappointed! We have been married 37 years and he retired five years earlier than I did, and as soon as that happened he once took over the entire running of everything. He told me he saw his job then as making my life easier. Do not hook yourself to someone who does not carry his own weight—being with the right person makes your life easier, not harder. Most of what you have described shows a life made harder by his presence. He may be a really charismatic and intelligent fellow, but over the long haul that is not enough.

    • Mable says:

      P.S. I meant to add that you seem like such a great planner and saver! I don’t know many people your age who have accomplished as much academically, work-wise and financially!

      • Olivia says:

        Thanks Mable! How your husband acted when he was laid off/retired is extremely sweet! Especially as winter comes, we’ll be having a chat about who needs to fill up the gas tank – I hate just standing there being cold!

        • Jenny says:

          I think maybe Mable’s point was that her husband did all those things “WITHOUT BEING ASKED”. He was an adult who saw what needed to be done and did it. He No chats, no cuddly budget discussions over beer…
          My friend is about 40 now. Her charming handsome BOYfriend had a hard time keeping jobs or staying in school. It was always someone else’s fault. His bosses did not understand him. They wanted to stay in business, not to just accommodate his needs. He has rich parents who bailed him out over and over. They supported them until she finished school. He never did. He had big dreams, but never followed through, so she works full-time, plus, while he “tries” to pursue a business his parents bought for him- one of several. But it now seems boring and requires him to go there and do things, so this made him anxious and they had to hire someone else to actually run the business. The other times in the past, he ended up running things into the ground. This made him feel bad, so he needed to go on solo vacations to feel better. Three kids later, he’s supposed to be a full-time dad and house-husband, but he’s decided he might be Native American and busy looking into his spiritual self, so they now have a nanny and cleaners, which the parents pay for, after a crisis where she threatened to leave. Oh, and he abuses alcohol and drugs so lost his driver’s license… “but he’s so cute and funny…I just love him…”

    • Anne says:

      What a sweet Husband you have!

      • Anne says:

        I also wanted to add that when I was in a relationship and not working (and the relationship wasn’t even very solid), I considered it my responsibility to do all the grocery shopping, cleaning, getting bedding etc for our new apartment, and meeting him at his office when we would have dinner together. I also pretty quickly started volunteering 25 hrs/wk at the place I would eventually work, all while keeping up the home work. I had the time and he didn’t. It would have seemed crazy to not be doing most of that. I’m really surprised (and disheartened) that Jacob sees things so differently.

  107. Katie says:

    Your story has been sticking in my head all day. I too have a partner with ADHD (well, undiagnosed, but we are pretty confident!) It’s been an adjustment to learn to work with each other. He’s very reliable – I always know he’ll do what he says he will, or that he’ll try his best – but he couldn’t handle a corporate office environment, for example. Instead he’s found working roles that give him more autonomy and in which he excels. Early on in our relationship, we were laying in a hammock together in a forest preserve while I told a story about my day. He interrupted me to share that “There’s a pile of sticks over there” while I was mid-sentence. I was taken aback, but now it’s a joke between us about his noticing everything.
    During our first couple years together, he was looking for a job, and perhaps I took on more responsibility than I needed to to help him. At this time, he’s again applying for jobs (while currently employed), and though he flatters me that I’m a better writer than him, I tell him I’m happy to help look over any drafts of cover letters, resumes, etc, only once they’re ready for me. We eat very different foods, so he doesn’t do any meal prepping, but he does the bulk of dog care, car maintenance, etc.
    I know you’ve received a lot of recommendations to end the relationship, and maybe the time will come when that does seem like the right thing to do. But it doesn’t seem like you’re ready to do that now. I think giving yourself (and him) some breathing room for a few months while he sorts out next steps (and while you have honest conversations) will help you figure out what you want.
    In the meantime, the best thing that I realized over time with my own imperfect, loving partner is that he does take in the things I say are important to me, and changes his behavior and attention accordingly when I say there’s a problem with something. It’s not just words to him or to me. I hope that Jacob shows you the same care and respect, or that you find a different life path that works well for you.

    • Olivia says:

      Hi Katie – thanks so much for these words. It’s nice to hear that you have a successful relationship that has some of the same challenges as mine. I really appreciate your sense that ending the relationship is not what I want right now. We have challenges, yes, but we continue to try different ways to address them. Some things stick while others need to be retooled and we’re working through that. Or some divisions of labor stay for awhile but then life happens and it’s weeks before I realize I need to say something to bring that great habit back. I do wonder if I’m maybe too accommodating overall and if I need to be more forceful with my requests. I know I’ve shared feedback and preferences, but I’m not sure I shared them in a way where he took them as change needed. To be honest, I’m not sure I meant them as change needed statements. I don’t want to be demanding, so I imagine my style in the past has been x, y, z are bothersome, with the hope that maybe one or two of them change, but then none of them do. I also am in a very different place emotionally now than I was when I submitted the case study – the appeal is over, I’m in a lull at work, and the holiday season is upon us.

      I will say noticing things is one of the nice things about dating someone with ADHD. We went on a hike recently and he just marveled at the nature around us and made me stop to actually lookup from the trail. I just would have kept walking, looking down to make sure I don’t twist my ankle on a rock. But he sees things I would miss entirely and shares them with me, and its things like that that are a real joy.

      • Gabby says:

        I struggled with a partner’s ADHD for some time. It felt impossible to leave because I really loved him, but our future plans were not compatible and he was not ready to take responsibility for his life yet.

        What someone told me then that helped is that you can love someone but that doesn’t mean you are going to spend the rest of your life with him. All of the great things you learned from the relationship will stay with you forever. It doesn’t mean he’s a bad person or that your feelings for him are not valid.

        Ten years on, he decided to turn his life around. He learned from his struggles and is doing great things now. I have zero regrets that I focused on my own goals and didn’t wait around for him to make those choices or continue to “snowplow parent” for him whenever he faced a crisis.

        While I was in grad school, I met a man who shared my priorities in ways I never would have dared to dream was possible. I owe my career and marriage to making the scary choice to prioritize my goals.

        You aren’t wrong to love someone who loves you. Please don’t blame yourself for that based on the comments. Just know that you are a woman of worth and options who deserves to achieve her goals and experience a true partnership.

  108. Gordon says:

    This sounds like a terrific arrangement…for Jacob.

  109. RG says:

    So I can speak to the last question about hitching yourself to someone with substantial financial difficulties. When I first met my partner he had been unemployed for a couple of years and underemployed before that for twice as long, and had not attended uni. He lived at home. I actually sat him down on date 3, poor guy, and was like ‘explain this to me bc I like you but this worries me’. He didn’t get a job for another 2 years. By the end I was seriously considering leaving him. Not because I didn’t love him, I loved him fiercely, but I knew I didn’t want a return to poverty if I could help it and I wanted a family and tick tock. Then he got a job, and I was relieved, and we soon got pregnant and here we are with a young child, me on part time hours, and he’s management. So how did I decide to stay?
    – I loved him. I got to where I couldn’t imagine my life without him, not really.
    – I considered the context of his financial situation. He’d been saving up to move out when suddenly he had to become a full time carer to a parent following a catastrophic health event. Not only had this decision saved his family money but it showed a care and diligence that I valued in a life partner. It showed that when disaster struck he’d be there.
    – He made clear and measurable progress towards employment, and he didn’t shy away from discussion with me about that. We sometimes disagreed about what progress was or should look like – I was more of the scrappy take- anything school and he wanted to be more strategic and position himself into a career, which paid off well for him and was the right thing in the end. But he did things like undertake training, connect with mentors, work on his CV, go on interviews and , more importantly, we could talk about it and even disagree about it while feeling mutually respected.
    – He still supported and respected my financial goals. If anything he stretched himself too much until we talked about the financial implications of our relationship on him (his gas to come see me was way more than I expected) and adjusted
    – He addressed some of the emotional and psychological issues around his unemployment. He did that without me. We could talk about it respectfully but it wasn’t my job
    – Even though our financial situations were different, we had similar mindsets about savings, frugality and consumerism. We both spent more than maybe we would have as singletons but not by much, and on experiences we valued. I certainly didn’t feel burned out by taking on his stuff, nor that my own security was being compromised, and TBH those aspects of Olivia’s account really worried me.
    – We envisaged a life together and this included loving discussion of how he’d contribute to the family even if the money stuff was never fixed. He would have loved to be a stay at home dad, and so that that was our plan B – we’d have kids, I’d stay full time, he’d be at home to cover childcare
    – He showed his ability to contribute in nonmonetary ways. Not just by his past experience as a carer but in the now – he gave me lifts in his clunker, picked up groceries, cleaned his share, picked up more responsibility when my work was busy, did DIY, and was a great provider of emotional support
    – He added to my life. Yeah I worried about him, and I had late nights with my girlfriends worrying, but he just made me so happy.
    So yes, it can be done. It was so hard but I guess the important thing is that you still feel like it’s a full partnership and like your own cup gets filled.
    TBH I saw a number of red flags wrt to Jacob. For one thing, ADHD can be a real barrier in employment, so if I were Olivia I’d want to know that he was working effectively with care providers to address underlying issues that might stop him being able to stay in a job (particularly as demanding as medicine). But the burnout, the burden, the absence of love in her account, really stood out to me.
    I read Attached and I rate it highly. Olivia, think carefully about whether you could be happy if nothing changed. You don’t need a ‘good’ reason to leave, you just need to want to.
    Oh also I was 31 when I met my partner, so not that far off on timing!

  110. Sean says:

    Taking out of the discussion issues of the residency firing or ADHD, Olivia is presenting a classic “two-body” career/relationship question. Jacob’s future almost certainly will take him away from where she lives with no likelihood of him being able to work in a residency or rural/under-served area near there for the foreseeable future.

    Olivia – do you want to move or relocate? You have a house you like, family nearby, a rich life, a location that seems great for the children you plan to have, and a job with benefits you want to be able to take advantage of. Under what conditions are you willing to sell this house and move away from your current job, family, and support system to follow a partner’s career? And at what point in a relationship are you willing to make this sacrifice for someone else, knowing that there are no guarantees?

    This is a hard question to answer, even if you had a current boyfriend or partner who had stable employment in another location and no reason to question whether they would be able to maintain it. There is nothing wrong with saying that you don’t want to move for someone else and continuing to look for a partner who aligns with your geography. No one has to be the “bad guy” here or do something wrong to acknowledge that you are on different life paths.

    Now – imagine that you decide you WOULD relocate for the right situation. What does that mean? What additional “burdens” will that place on the person whose career or preferences you choose to follow?

    No one can tell you what the right answer is. There is no right answer. Strip away a lot of the details and see whether there is ANY person who makes these choices right for you, and, if there is, at what point you can decide if THIS is the right person to take on these risks for.

  111. Soggy Suzzi says:

    Something I forgot: To put a fan in the bathroom, you need to make sure it is vented to the roof. Don’t vent it to the attic, it creates mold in the attic over time and it will take professional remediation to correct. Cost: A good bath fan can easily be had for $30 to $50 max. You can pick one up at Lowes or some other electric supply store. A good handyman can install same in less than one hour. There will be some piping for the attic, and some waterproof glue and vent for the roof that he will provide, so the total bill for fan and handyman should be no more than $200 total to do this minor job. You are being seriously overcharged for this simple fix. Ask at the store you buy the fan from–around here they have a list of recommendations for installers.

    Hey Jana, nice to see your post. How are the book sales going? Have you started another one yet? Good post for Olivia.

    • Kim Klaproth says:

      YES!!!!!! That exhaust fan – I meant to comment on that as well. That is an outrageous price. It would make me question a lot of charges if that one is so over the top.

  112. Kim Klaproth says:

    Olivia, I have a lot of red flags about this relationship. He should be doing a lot more to support you since you are the one working. At the very least he buys all the groceries AND does all the meal prep, including your lunches. When a person is unemployed that is when they should be showing their most frugal side. If he isn’t frugal NOW, not sure how compatible you guys will be financially. If you guys remain together I think he needs to find the way to remain in your location since you are the one settled. Do not give up your job and home to follow him wherever he may land. Set a time limit for how long he can be with you without working or finishing his training. You don’t want 3 months to grow into 12 months without boundaries being established. I know this is hard to do when you’re in love, but I’m just trying to be a big sis via the internet. You are a strong woman and have your act together, I don’t want anything or anybody to derail that.

  113. Jenny says:

    Having had experience with supporting a husband/partner, who foresaw a bright future for himself but just wasn’t able to put forth the effort that was required to get there, and having professional experience with treating adults with ADHD-related issues, I would just ask this: if what he is doing now is all that he will ever really be able to do, would you want to marry him and have children together? If he is not able to be a doctor, does that change things? Because being a practicing physician is a lot more challenging than residency, most likely! Do you see it as being a little bit of a mother and wayward son dynamic? Of course, I don’t know how the day-to-day is, and whether his charm is worth it! But if this is as good as it gets, how does that make you feel?
    Wishing you peace and all the good things…

  114. Reece says:

    Need to be blunt here: ditch the bum. You are rationalizing the heck out of this situation. He needs to have some kind of income tomorrow (deliver pizzas, Uber, whatever) and needs to have his own place to live within a few weeks. He won’t do this though, which should set off 100 red flags about this situation (especially given your clear goals to be financially independent and accomplish something with your life). That aside, I strongly encourage you to assess jobs that pay significantly more than you make now. In the DC area you are living at the poverty line, and while we millennials love to sing praises about “doing what you love” I promise you a lot of people making $50k, $75k, $100k, $200k+ Really enjoy what they do too… you are too educated and have too many great and admirable goals to keep yourself at such a low paying position. It’s great to be frugal, but doubling your income will achieve so much more than frugalizing every last penny can achieve. In all honesty, this was a hard case study to read because there’s a ton of potential but the bum boyfriend and safe job choice are holding you back. I won’t win “most compassionate comment” award but as a 31yr old guy I’m calling it as I see it. All the best!

  115. Laura says:

    Jacob’s unemployment not related to your equity. With extra cash, I’d put extra towards equity so you can get rid of PMI. Don’t stress about it. You have a good interest rate. My interest rate on my first house was 10% in 1989! Times have changed. Take the money from accounts earning no or very low interest, but I’m no CPA. Your new appraisal will be based on any improvements you have made. Wait to do appraisal after your latest improvements (if the time horizon isn’t too long).

    No reason Jacob can’t get a very part-time job to help offset living expenses (his and/or yours together). It doesn’t take all day every day to search for a new residency. I work in healthcare as a dietitian – work with residents.

    Not charging rent is fine as long as he is working a little bit.

    Love & debt: Not knowing you both, I’d say, see how things go over the next year with him getting another residency. It’s possible it will be great. Red flag if it doesn’t work out for him a second time. Then you will know that it could be a long time living with a debt burden. If residency goes well, likely job prospects will be good. There is a shortage of physicians. If he gets passed everything, he will do ok financially. If you marry him, you could have a pre-nup drawn up, maybe keeping your assets as yours and not taking on his debt (see an attorney for that).

    Early retirement: If you marry everything changes. Married people usually share a life, including vacations, finances, dreams, children, etc. Compromise is everywhere! Physicians put so much time into their education and training that they usually want and need to work at least until into their 50s. If they love what they do, they want to work longer. Some retire sooner and it can be done. Look up the White Coat Investor and Physician on FIRE for more information for physicians. I’m in my 50s and as much as I get the desire to be FIRE, once you are there, as my husband and I are, it’s no big deal and you end up a bit without a purpose. Kids grown up, volunteered out, not really feeling needed anymore. I work 2 days a week for fun and intellectual stimulation. My husband could retire, but he likes his role, so why retire (he will at 60 when it’s mandatory). I travel alone to see friends and family while my husband works. I’ve been doing this for years. It’s fine!! You can do this while your husband is still working, but you may want to discuss this first.

    Bottom line: It’s risky to make a decision to marry Jacob at this moment. Give things a little more time or decide to end relationship. Watch, but trust your instincts. Also though, having children without a partner is harder than you may expect. I’m not sure I’d do that either for myself and for the child. Certainly don’t risk all you have worked for financially. Divide up household chores as well. I didn’t do enough of that and kind of regret it.

  116. Laura says:

    I also work in functional medicine and thought this article would be of benefit to Olivia and Jacob. There are good natural treatments for ADHD. See this article from Dr. Mark Hyman’s Office. He runs the Ultra Wellness Center, a well known functional medicine practice.

  117. Ms Blaise says:

    Hi Olivia, I had my children at 43 and 45, without any IVf or anything, just the old natural way, with my partner of 10 years. When he moved in with me, he quit his job that he hated and I encouraged him to wait until he got into the police, which was what he wanted. I was renting, as a teacher, and said I was happy to keep paying the rent. I owned my own house in another city and had it rented out, and we didn’t combine our finances. By the time we bought a house together a few years later, he was well into his new job. The unemployment had lasted maybe 5 months. During that time he exercised every morning ( for free) did all the maintenance , shopping, cooking and housework, and spent 0 money. He gave up alcohol and focused on becoming my financial partner as well as life partner. I was super impressed, though sometimes irritated by it.
    Two kids and a mortgage later ( which we have nearly paid off), he finally earns more than me. We have both had career changes. He did his masters while working full time, I did a phd which I pulled out of when my second daughter was born as it no longer mattered to me. My other house is still seperate in our wills and the $ will pass directly to our daughters in trust should I die .
    I manage the money, but we discuss financial goals and progress each payday, and he spends only what is in his spending account. We give ourselves each the same amount of sanity money each pay.
    My two cents worth would be to have separate places of residence even if you spend every night together. I totally get that he is your person.
    There is a great American book from the 1930’s called Orchids on your Budget and in it there is a chapter on marriage. In it, she gives the advice that if you want a husband or a child you should have them, if you can afford them. No one expects a child to contribute equally, so why would you expect a man to (!) A different era, but its a fair point. If you want to, and you can afford it, go for it.
    Ms Blaise.

    • Mable says:

      I would expect a man to contribute equally (if he cannot financially, the job becomes taking care of the house and the outside and you) because he is not a child. If he does not and the child does not, the woman ends up being the only adult.

      • Ms Blaise says:

        Which is great for you. But not everyone has to have the same “equal” relationship. If it works for them another way, then that’s up to them isn’t it? No one really knows what goes on in another relationship. There are a load of trade offs, deals and compromises made. You could both contribute “equally” and be miserable.

    • J says:

      The author of “Orchids on Your Budget” also wrote a great book about being happily single! It’s called “Live Alone and Like It” and you can find it online or at an antique shop!

  118. Barbara Barry says:

    You are doing amazingly well, I admire so many of your choices and accomplishments. You are doing great financially and buying the house was Brill. Don’t sweat PMI, I didn’t…I ALSO WOULD NOT put any money toward it but rather keep it in a savings vehicle…in a year comps may show an increase in value and 20% equity. PMI is not your problem…

    You are young and have dreams…which you have shared with us. Go for your dreams…better jobs, great vacations, buying a house, looking for love…a man who cares about you and for you. I don’t think Jacob can do that…and neither do you…you don’t need his rent, not that he is paying you any, to thrive and you are stressed to the max trying to take care of him. His debt, his job problems, his not working, his severe issues. You cannot have any kind of relationship with him other than parent, caregiver and financier. Ask him to leave and move back to his family and call you when he gets his life together. Then you start being happy by yourself and dancing again…yoga! Enjoy your job and enjoy your house. NO…a raise doesn’t mean you have to work more than 40 hours a week…smart people figure out how to get most important things done in 40. Take lunch hour. Eat lunch. Stroll through campus. Weigh next steps career wise. People who work in education think that another degree solves everything…it does not…you have enough education already…take a break, when you are ready, find a job that pays $20,000 more a year…do some volunteer work, join a pickup volleyball team, find more men friends and maybe someone to love. I didn’t have that Someone at 31… but I found him at 33! On the volleyball court! Ha! 34 years and two kids later. …You deserve to be happy and carefree…no more emails from attorneys… Good luck to you!

    • Cara says:

      Olivia, listen to this woman. i would add that you are entering your peak earning years, which are fewer than you think, because ageism is a thing. Also, best of luck with your parenting goals- to that I would add that kids require lots of your time and energy, and more (but not loads, necessarily) money. What I am trying to say is: your resources are limited, and so is your financial potential, over the long term. You’ve done really well building your future. The hole that your boyfriend has dug will not add to it.

  119. Aurora Leigh says:

    Hi Olivia!

    First, congrats on all you’ve accomplished! I have no finacial advice to give — you’re way ahead of me.

    I know you’ve gotten a lot advice about Jacob, but your relationship is still new (less than a year if I read it right?) and I think you’re both allowed to still be figuring things out!

    It’s hard to figure out how to live with someone and share responsibilities, especially when you’re used to single life and doing it all yourself anyway. My fiance and I have been together 2 1/2 years and we’ve come a long way, but we still have lots to figure out!

    When I first moved in, I filled half the garage with stuff from my apt that we didn’t need, but I didn’t want to give to Goodwill in case things didn’t work out, and I needed it again.

    Different standards for housecleaning, cooking, etc take a lot of time and talking to work out. I think that people who have been together for a long time (or went directly from living with parents to living with SO) forget how awkward the early days could be.

    We both panicked about moving in together during the process, but now we can’t imagine not living together.

    I’m a planner though, and if Mrs Frugalwoods had asked me about 10 year goals when we had been together for 9 months, I definitely would have still been planning for both possibilities (single or coupled). So I don’t think it’s a red flag.

    As far as division of labor goes try being very direct . . . I have much better luck with “would you please” than “I wish you would”.

    I would give him a few more months and see what he is like with steady employment before throwing in the towel.

  120. Emma says:

    Hey Olivia, I see a lot of people have already weighed in on this but the honesty of your situation really spoke to me so I also wanted to share my insights as a 30-something who has just supported my husband through a long period of unemployment (15 months).

    My situation was different to yours, and I was more than happy to support my husband while he needed to be off work for his health, and I would change not a single thing about our choices during that time, but boy has it impacted upon my own financial stability. I have not gone into debt over it but my assets have plummeted and that’s something I need to live with. If I were asked to make the same choice again I would without hesitation, because I KNOW that my husband is the one person for me, and also that he would support me in exactly the same way if I needed it. But I ask you: how would you honestly feel if you were to lose 50% of your assets right now looking after Jacob? 70%? 80%? And would Jacob do whatever it took to look after you if you needed it?

    It also really struck me that Jacob has not been assessing his own spending while away from work. It grates on me that he would choose an expensive birthday outing during his period of financial instability: it makes it seem that he’s not taking responsibility for those matters in his control right now. It makes me wonder how financially literate he is. I totally agree with Mrs FW that if you truly want to be with somebody their debt will never be the deciding factor (although you may choose to live financially independently – there’s no requirement to marry, after all), but would he be willing to look at his own financial position head-on? Would he do the FW frugal month challenge? If not then this looks like a deeper problem to me than his debt.

    Finally, I strongly recommend you reconnect with your own life and needs. You say that you desire to be able to do yoga 5 days a week, well you can have that in your life today! Book that yoga class and clear out the storage room (could Jacob work on selling the excess?). Sometimes the gap between what we desire and what we currently do is so close it just takes a tiny push to have what our soul needs. Not everything needs to wait for a 10-year plan! Also it will help you not burn out, which in itself would derail everything you hope to include in your life, financial or otherwise.

    I really hope you have found the help you need on here. Know that we are all cheering you on and best of luck with whatever you choose to do next!

  121. Anna says:

    I can only agree with everything that has already been said. I also read so much doubt between the lines about this relationship. Another thing that alarmed me, or that i was wondering, is Jacob’s willingness to pay off debt and do his share of the work for your future… what is he willing to compromise? So far, I have only read that he wants to move to a place that is important to him… regardless of the fact that you live in an area you love, he wants to go to Six Flags despite the debt, and he is not interested in FI. I just heard so many alarmbells while reading your story. I think Dorf just really summarizes it well. Of course we cannot look into your life, but your story does not show a lot of enthusiasm about this relationship and it is really important to consider whether the relationship is because of fear of being alone, or because it seriously adds something beautiful to your life.

    To finish, me and my partner have had a similar episode, where he was unemployed and I was working. I admit that is not easy and puts a strain on any relationship. However, this did.make his move to where I lived easier, and as long as he didn’t work, all the household chores were his responsibility.

  122. RG says:

    I want to add something as I’ve thought about it overnight – about how much work is really needed in a relationship. Olivia I was also single for many years before meeting my partner. The relief at finding someone! But. Those many years on my own, with only myself to steer the ship, also meant that it took awhile to reset my barometer of how much work is tolerable in a relationship. I had many reasons to think that an intolerable amount of work was actually ok. I was not able to actually be in a healthy relationship until those parameters were reset and that took some work and reflection from me. All this happened BEFORE I met my partner. It is a big life transition to go from single to coupled. The well-being and happiness of each individual in the relationship matters as much as the relationship itself. There are no prizes for martyrdom, no prizes for facilitating someone else’s transformation (which ultimately is a fool’s errand). Maybe this resonates but maybe it doesn’t. But being in a relationship doesn’t and shouldn’t mean that one person’s well-being is compromised. Putting yourself first isn’t necessarily an unkind thing. Myself, I could see every day that my partner was working to get out of unemployment, and I could also see that his work as an unpaid medical carer was its own form as work. Our relationship flourished even as it was shaped by his unemployment, but I still got to do me – I progressed in my career, had great holidays with girlfriends, pursued my hobbies. Who a person is in a crisis is also who they’re going to be when they’re a sleep deprived parent, for example. The internet doesn’t know you or Jacob but the way a person tells their story is very revealing. If your account had been written by a friend, what would you think? Would you worry?

  123. Katie says:

    Hi Olivia! I just wanted to pop in and say that I think that you are an amazing person and that it was brave of you to submit this case study. I won’t comment on your relationship since it seems that many people have done that, and I trust you to decide what’s right for you!

    Something that really jumped out at me when I was reading your case study is how hard you are being on yourself in terms of how you are managing your money. You seem so concerned about your PMI and your eating out budget, among other things. I just want to encourage you to zoom out for a minute and look at the big picture. You have made very good financial decisions, putting you in an incredibly strong financial place at a very young age. You are living in one of the most expensive cities in the country and have very low expenses overall. You are putting more into your retirement accounts than you spend each year, even with increased spending due to stress. My perspective is a little different than other readers, since my goal is not to FIRE as soon as possible, but I think that you need to take a breath and give yourself a break. Just keeping things the way they are right now you will be close to FIRE in 10 years.

    For instance, with the eating out budget, I totally understand if you would rather not spend that much each month. However, I don’t actually think that the money is the issue. I think that you will feel better, eat healthier food, and spend more time cooking (which is something you enjoy) if you eat out less. I think that making changes with that goal in mind is more important than lowering your eating out budget to a specific amount, and feeling stressed if you don’t meet that goal.

    Maybe I am wrong, but I sensed that you are very hard on yourself and have specific ideas about how much money it’s acceptable to spend in certain categories, and that you stress if you don’t meet those goals. I just want to encourage you to look at the overall picture which is that you are in a FANTASTIC financial place, especially at 31. I think that you should feel incredibly proud of where you are in life and should trust yourself to make good decisions going forward. We are rooting for you!

  124. Nessa says:

    Hi Olivia,

    I admire your job, your home and your location. Well done, you did all that! When l read your boyfriend’s amount of debt, l gasped and my eyes watered. I am going to be blunt, and you may be exhausted of reading comments by now, but, what does he add to your life? And now into pop psychology, do you have a blind spot around men? Was that too much? I think there is a boundary problem there. You’ve looked after yourself really well but, are you giving it away because you dont feel you deserve it?
    This is definitely going to be rude, (Sorry Mrs FW) but l read it on mumsnet and thought it a brilliant term. Is he a c*ck lodger? A man who moves in to get free rent. When l heard he has over 200k debt, was fired and then moved in, l had to wonder.
    That you have given up yoga and taken on his stress is a red flag IMO. If you want to be a mother, that is your choice but be very mindful that your partner will be that, a partner because mothering is hard ass (Sorry for cursing, l’m Irish, we love a good curse) work, big time! Those future little ones need present and invested parents. That’s probably the crux of the issue, is he dad material? Right now, is he is more of a child? Are you parenting him? Now really for my opinion here we go. He is a liability, sorry if that stings, l want you to have a good life with less stress, because stress is a killer, long term. If you were my daughter, l would want him gone. I would want her with a decent and functional partner, debt free and ready to give me grand babies.

  125. Karen says:

    Hi Olivia, sharing your case study has certainly stirred up a lot of advice and support! This is a tribute to how you’ve made your way in this world. You’ve stirred up a lot of warnings from people and a lot of congratulations for building a financial and professional life. You must refocus your mighty power to build your emotional support system-exercise, community, family because you’re about to make a big decision about Jacob. You have so much agency and power, recognize this and don’t let fear of loneliness keep you from recognizing the partner you deserve to walk with through life. You deserve a compassionate partner who lifts you up, inspires you, respects you and shares your values. All the best to you Olivia.

  126. A psychologist says:

    Olivia, you don’t mention if Jacob is being treated for his ADHD. Several other people have mentioned this but I’ll chime in as well as a psychologist and the mother of a son with ADHD and wife of a husband with ADHD. He absolutely needs to be in treatment. ADHD impacts functioning not just in the workplace but at home as well. Symptoms present themselves in a myriad of ways but can include looking lazy (like not doing household chores/yard work) which is really just a failure to self-initiate. He may not be able to process his own legal documents without help if he’s not properly treated. People with ADHD frequently impulsively spend money because their brains don’t have the ability to “put on the brakes” and delay gratification. It’s a neurological disease- not a disease of character. There’s a lot of bashing of Jacob in these responses but he’s clearly someone you love and he’s obviously an intelligent man having made it through a masters program and medical school. I wish you both the best of luck whatever your paths are. You might want to check out CHADD which is a major ADHD support organization.

  127. KCF says:

    Oh, Olivia! I have read all these comments and will not regurgitate the very sound specific advice everyone is giving you. As a mother of three adult daughters, one who has significant challenges similar to Jacob (so I don’t want you think I’m being too judgmental), as someone who works in healthcare and sees the enormous red flag of Jacob’s firing for what it is, and as a wife of 30+ years through ups and downs, I will not sugarcoat this for you: walk away, honey, walk away. You have all the goods to make a wonderful life alone or with another partner who is better suited for you. Walk away now. You deserve so much more

  128. Christine says:

    Kudos to Olivia for posting a very personal Case Study and being in such a great position in life. I have never commented before on these but this one struck home. I am a physician and it is exceeding rare for a doctor in training to get fired from residency. It’s so difficult to do it that programs usually don’t try. Gross negligence or willfully not showing up etc. If Jacob cannot hold down a residency position and then any sort of job or help around the home at age 36 he will likely NEVER meet what you deserve as a life partner. Please think through carefully before becoming more entangled. If he is the right one he should be willing to make sacrifices for you as well. Best of luck in your decisions.

  129. CKW says:

    Hi Olivia,

    You are Killing. It. with your life setup right now and I so wish I still lived in DC so I could be friends with you! It sounds like you really love Jacob and the financial slant of your writeup has caused you to leave out some of the less tangible contributions he’s making to your partnership, which I think is causing lots of folks to pile on with the DTMFA (a la Dan Savage) comments. Since he contributes enough to your life and your lives together at the moment that it sounds like you want to stay together at present, let’s focus on your questions about the future. Also, guys, given all she’s contributing to retirement, by my math she makes at least $70K a year, which is perfectly respectable and livable, even in DC, especially with her tiny mortgage. Anyway, your questions:

    House: It’s up to you how much the $ you’re paying towards PMI bothers you. If the math works in its favor, then kill it quickly. If not, it’s just part of your pre-loaded expenses and will eventually go away. If you do cut down on your retirement contributions, keep all you pre-tax contributions to ensure your lowest tax burden and cut down on the Roth contributions first. Personally I would max out both tax-deferred accounts (this is what we do) before I contributed to the Roth, but you’re doing great either way so it’s really up to you.

    Partner: Being unemployed is tough/depressing, especially if the situation has been up in the air until recently, and with the added burden of ADHD, I imagine Jacob has had difficulty structuring his time/days. When my husband has been unemployed or had working hours change, it was helpful to specifically articulate how household/shared duties would change between us, given his freer schedule. It helped him to restructure his time (might be helpful to use the absurd but not untrue “units of time” framework from the movie About A Boy) and put specific things on his plate that would help us as a couple and a household. A few people have mentioned under/unemployed partners automatically picking up all the slack, which is nice, but some people need a more applied, request-based approach to determine how things should change and it sure couldn’t hurt things for you two to decide them together! If it turns into you always being the cruise director/manager/requestor/mom, that is also information that is good to have going forward. Also, I would watch him like a hawk for depression and encourage him to continue self-care activities, including good nutrition/sleep/exercise, etc. And I would suggest you do the same for yourself!! It’s hard being the partner that is giving more at the moment (no partnership is ever 50/50 exactly all the time), and you have to make sure your well doesn’t run dry. So get back to yoga when you can and have someone (Jacob!!) do (simple and quick) meal prep to manage your stress both for yourself and to be a good partner.

    As for rent, it’s just $, which is nice but you don’t really need it and he doesn’t really have it at the moment. So if you don’t charge him rent but he is contributing to the household satisfactorily in other ways, it’s no big deal. Again, what matters is what YOU and HE think. Does he WANT to pay rent or contribute monetarily? If so, perhaps you should let him. If not, that is interesting information to file away. If he’s not contributing non-monetarily to your satisfaction, you need to speak up and make your needs known (in my own relationships, I’ve always been surprised by the extent to which my partners have not been mindreaders), or you might as well just charge him rent to make things easier/clearer.

    It sounds like you’re doing great with a life goal backup plan, so if 1.5 years together haven’t told you whether or not Jacob is your partner for life (I understand, took me longer to decide as well), then just keep going for a bit until the job stuff for him settles down so you can reassess when his path is more clear. As for his debt, a lawyer friend of ours had a prenup written so his wife would not be responsible for his enormous school debt. You might not need Jacob to do this but it might be telling whether he would WANT to do something like this to protect you, just in case you guys didn’t work out. Attitude REALLY matters. We had another friend who supported her husband all through med school and residency, only to have him dump her (basically penniless) as the $ starting coming in once he started practicing. Only you know which scenario is closer to your own relationship. Professional school debt with high earning potential is a weird animal and might not be a big deal in the long run (my sister is a doc, had a ton of debt, and now it’s gone), if you two are on the same page as to tackling it and lifestyle during the paydown period. As many above have noted, working together towards shared goals (be it FI or RE or both) is the thing that takes you into the future as a couple, and can make up for a lot of financial sins of the past.

    This is already a tome but some food for though – does Jacob know you’re doing this case study? Why or why not? Would he be comfortable reading your words/ Liz’s advice/these comments? Would you? Would they make good discussion topics between you? I know how I would want my partner to respond to these ideas but you need to decide for yourself.

    Finally, yes, lots of apparent relationship red flags crop up in your case study (I actually think the Vermont/vacation property things are way bigger issues than the debt if you stay together), but I’m a big believer in the power of change. No one and no partner is perfect, and what matters to me (and again, YMMV) is that people can, want to, and make measurable steps towards resolving issues once they’ve been identified. We have a lovely friend that is kind of a doofus in life (his words) and even though we’ve had our conflicts, he’s still in our lives because he’s always willing to talk things out, listen to criticism/advice, and try (doesn’t always succeed) to change for the better for the people around him. This is such an admirable quality and takes the sting out of many of our issues. Only you can decide where your line is (you do mention that he communicates but things don’t change…) and if Jacob’s attitude towards finances, your partnership, and the future works for you.

    Ooh wait, one more thing – can’t you start classes towards your degree before you go full-time? You could probably figure out, once you identify the program you want to join, some of the core classes for the degree, and since you work at a university, chances are you could knock out some early requirements for free at your current school. That could help you push the grad school timeline back a bit, as long as you could get credit for those classes, if you need time to decide on other matters.

    Best of luck.

    • Chris B says:

      A few points to add on:
      1. My husband’s financial habits and outlook also changed greatly during our marriage. He was unemployed and sleeping on a friend’s couch when we met. Mine improved also, as we learned and got on more stable footing. *However*, at every turn, his decisions showed me that he had the seeds (so to speak) of how I wanted to live and meet future goals.
      2. My EX-husband was better “on paper” and off financially in the beginning, but his habits, outlook, and decision-making were NOT coincident with mine. A disaster, and eventually I got tired of being sad and miserable all the time.
      3. The Family of Origin question is huge. Is there usually support/hand-holding, which prevented growing up? (EX husband had that, too) Why all the solo decision making about vacation homes and moving?

      In contrast: My current husband 🙂 happily bowed out of his family’s sacred vacation cottage because a) its a PITA with too many people involved, b) we will never go there, and c) his family is loony toons, so why create legal and financial ties to what is guaranteed to be a mess one day. Oh, we met in my 30s, had a two year long distance relationship-very eye-opening, and he would never in a million years be ok sponging off me for any length of time.

  130. Silver says:

    Dear Olivia,

    My father was a simple man of few words, but this pearl of wisdom spared me what could’ve been the hugest mistake of my life; I pass on his warning to you with love, just as he did for me:

    “He’s gonna ruin your life!”

  131. Leigh says:

    Longtime reader, first time commenter. Olivia, I’d ask yourself the question, “What does freedom feel like?” Meaning, does it feel freeing to be with Jacob, or does it feel freeing not to be? To me, the fact that you can picture yourself happily raising a child without him is a sign that he just doesn’t bring enough good stuff to the table. While difficult in the short-term, I think you’ll feel a weight lifted off of your shoulders if you move on from this relationship. Could be wrong, but wishing you the best as you sort it out.

  132. Pixie says:

    I’ve read through virtually all the comments (I skimmed some of the redundant ones) and am eager to know how you hear all the comments (especially the repeated ones from physicians about the red flag of being dismissed from residency) and where you end up. I strongly think you should commit to therapy/counseling for yourself, as long as it takes.

  133. Daisy says:

    Thanks for sharing your story. That was brave.

    Like many here I agree that the relationship is the main issue when considering Olivia’s finances. Prior to the relationship she was doing everything right. The relationship has created some wrinkles. Okay, lots. The main thought I have is that we know that one’s relationship is often the single biggest influence re: finances. Having an on-board partner will have a positive impact on finances, wealth accumulation, etc. Having someone who has a different approach to money and debt will have an equally significant impact – just not in the same direction.

    While I don’t want to minimize the stress of unemployment, I do think it is important to remember that most lifelong couples experience challenges – some pretty significant. You need to be able to deal with them as a unit. Challenges are hard enough without financial “derailing”. How will Olivia and Jacob manage the inevitable life stresses of job loss, ADHD, as well as other curve balls life can throw such as the stress of parenting, limited finances, debt, caring for family members, illness, disability, death, conflict, and so on. My concern is that what little we know about this couple suggests that this is a relationship at risk to struggle with the “crap happens” of life. If Olivia remains in this relationship and the underlying relationship issues are not addressed financial security is unlikely, and the relationship itself will be at risk.

    Jacob is a man who has reached the latter half of his thirties with little to no employment history and significant debt. 36 is late to do a residency, What was he doing before then? And, while he is now a student in a field where large salaries are possible, there seems to be red flags. Lots. Being fired from a residency is rare, and kind of a big deal. In the absence of counselling and work to address the underlying causes for his termination, there will be ongoing concerns about his employ-ability.

    My two cents for what it’s worth is that if Olivia chooses to remain in this relationship Jacob should move out and get his act together. He needs financial and professional counselling,. Once Olivia is assured that he can independently deal with his stuff, then perhaps consider living together. Do no marry without a prenup. I also would suggest that Olivia independently if Jacob sees a counselor to unpack her reasons for being in this relationship. While I know we only have a curated snippet online, I do not get the sense that Jacob is the love of her life.

  134. clara says:

    Another physician here, and as one who has worked in a residency, to echo everyone else, it’s hard to get fired. They do various remediations for lack of knowledge, poor bedside manner, poor communication etc. Firing is a last resort. An earlier physician commenter noted that life in practice is actually much harder than residency. I would disagree, my residency was one of the hardest times of my life emotionally mentally and even physically with lack of sleep. Practice is so much better but one thing that doesn’t go away is boring administrative tasks. I do not have ADHD and I sometimes struggle to get it all done and not waste my time or procrastinate. That being said, it sounds like Jacob is sociable, fun and smart so maybe he should consider other work in the medical field like being a drug rep or doing some other thing that might fit his personality better.

    Also, wanted to comment that mental health treatment can be hard to admit you need and then access. I think this is it even more true for men than for women as I think there is more social stigma for a man to need help. My husband told me once that he didn’t need a counselor because he could just talk to me. Due to the stress we were dealing with at that time I gave him a near ultimatum that I absolutely would not be his counselor. He ended up finding an amazing counselor who has helped so much more than I ever could because she is actually a professional and knows what she is doing. If he can get over the hump and get actual professional help, That would go along way toward proving to you that he will not be your problem to deal with.

  135. Kate says:

    Hi Olivia!
    A couple of thoughts-
    If Jacob is in NHSC is he planning to pay back loans with money? Most likely he’ll pay them back with service, right? I didn’t do NHSC but friends did and never paid a dime to their loans. At $25k/year they’ll be gone in ten years.

    I also think you will love your mini split. We put one in this year and I can’t stop raving about it.

    • Coral Clarke says:

      Olivia,perhaps what might be useful would be a “Starting today…..” discussion with Jacob. Knowing what he wants to have happening in 1,2,5,10 years, in regard to finances, career and relationship goals, and how he intends, specifically, to reach those goals.My best guess is that he will need some professional help to sort that out, but I don’t think either you or he can go anywhere, together or separately, without a roadmap.This is particularly true for anyone battling ADHD, whose need for a specific “recipe” is greater than it is for those of us who find focus easy.His willingness to do this will allow you to see realistically what his commitment is to a shared future.People with ADHD can have surprising clarity about their need to set a program and follow it, but will rarely come to that realisation unprompted, and will almost always need help setting up action plans and time markers , etc. None of this is entertaining, but it sounds like you both want to find a way of moving forward together, and value you each other highly enough that it’s worth putting in the hard yards, worth giving Jacob a chance to show that he can be a partner, not a project !! The critical point is the professional guidance, without that it can become a plan so general that it’s not measurable, and therefore a waste of time and energy. Give your relationship the best possible chance of success , and know that the result achieved will be the best result possible.

  136. Dana says:


    Without knowing you, you sound like a truly amazing person and inspiration to us all. Your financial savvy, work ethic, personal motivation, and deep care for others are evident. You seem well-rounded, engaged, productive, and like a wonderful family member, work colleague, community member, friend, and girlfriend. You have everything going for you – health, career, finances, goals for the future, and positive outlook. You are a true catch – any man would thank their lucky stars to be by your side. I hope you know that.

    I won’t pile on to what others have said regarding your relationship, but I do agree with many comments out of concern for you. What I would like to add are a few observations and what are hopefully received as words of encouragement. Please do not take my comments as judgement, but as my sincere attempt to convey empathy and support from one 30-something woman to another.

    1) From what you’ve shared, your relationship sounds very one sided in the daily management of your home. I gather there are many special emotional moments between you two, otherwise you wouldn’t still be committed to making this relationship work, but on the day to day, it seems like you’re pulling both your weight and his, exhausting yourself and not leaving space or time to fill up your tank. I’m no expert, but IMO, relationships – especially marriage – aren’t just about warm, fuzzy feelings – it’s important to be with a stable, loving, generous partner who is able to contribute to a solid, stable home. What that looks like is entirely your business – as other commenters have shared; an equitable division of labor looks different for everyone and what matters is that it WORKS FOR YOU. It doesn’t sound like your test run at domestic partnership is giving you the stability you need to thrive in your life; it’s oriented around your partner’s need to get on his feet and survive the day to day. Your household division of labor and general operation is meeting Jacob’s needs, but not yours. That’s not fair to you. It needs to go both ways and you shouldn’t have to repeatedly tell Jacob to care for you. Just because he has ADHD doesn’t excuse the fact that he doesn’t seem to be trying his hardest to give to the relationship and home like you do tirelessly 24/7. No wonder you are exhausted and barely finding time to eat lunch, exercise, or do chores that make your life run more smoothly; you’re giving everything you have to work, Jacob, and your home. Who’s giving to you? Who’s making space for you to nurture your mind and body?

    2) From what you’ve shared about your profession and goals for the future, you’ve a very empathetic, caring person who wants to make the world a better place, have a stable home in a nice community, and have a family of your own one day. You support people and want to see the best in them in your job and life. You are an amazing giver. I wonder though if you’ve gone into overdrive, digging deep into your caretaker tendencies to manage what must be an incredibly stressful relationship and home life. As a highly driven person, it sounds like you’re trying sprinting at work and at home, to keep it all together. Jacob sounds like he’s having a major life crisis, which is very difficult for you both, so you’re doing everything you can to help lift him up. I commend you – you’re amazing, but, I have to ask – who is taking care of you? You give so much and you deserve that in equal amounts. I think what other commenters are trying to convey is that you deserve for someone to see you and find ways to care for you in the ways that they can, despite going through it themselves. This is emotional maturity and the generosity you deserve. Even if Jacob can’t work full-time right now, there are so many things one can do to contribute to a balanced, well-functioning and supportive home (listed by many others – cooking, cleaning, loving care, efforts to make your needs a priority). You are more than fair and let Jacob off the hook because you see he’s struggling and also has a disability, but I wonder if you’re also using that disability as a crutch to avoid seeing that he might also lack the skills to be the partner you deserve. I’m sorry if this is harsh, but having been in a similar relationship, it was easy for me to use ADHD as an excuse to ignore the fact that we were just not compatible and that was only the tip of the iceberg. Don’t confuse ADHD with a lack of the maturity, selflessness, and dedication required to make an adult relationship thrive. You should know what those things look like because you give them without thinking day in and day out.

    3) Don’t settle because you’re afraid of being alone. Easy to say from behind my computer, but having been in a very similar emotional place throughout my 20s and early 30s, I know how hard it can be to see everyone you know get engaged, get married, and start to have a family. You have your first serious relationship in a very long time and you’re trying desperately to make it work by focusing on the positive – Jacob might become a doctor, he sounds like he is close to a family with some wealth, and he brings light to your life. I’m sure there is much more, but, there is a lot left to be desired by you which has become evident in your premature dive into a domestic partnership, motivated by your desire to support and nurture Jacob during this very hard time. You are so ahead of the curve in so many ways – you’re incredibly professionally accomplished – already having a Master’s degree and on track for more, already situated in a career path you love, own your own home, have a wonderful family, and have a rock solid financial life. The things you have going for you can take a lifetime for many to build. Marriage and a baby are not the only life success metrics, though I am 200% certain that you will find an amazing partner and start a family, if those are your goals. You don’t have to settle for the first option that has come your way in a while. Please know that you deserve a relationship that makes your life generally EASIER AND BETTER, because otherwise, what’s the point? It would be much easier to stay single and focus on meeting your own needs, than with someone isn’t capable of that for one reason or another. You have so much to offer and deserve that in return. Repeat – you have so much to offer and you deserve that in return.

    I have so much more I want to say to you, but this is your journey and only you can live it. Maybe things will work out with Jacob and if so, I wish you both a lifetime of happiness. Don’t be afraid though to prioritize yourself, your needs, goals, and wishes – it’s far better to be alone and focused on your own growth, than with someone who can’t support you or your needs in the most basic of ways. If it’s helpful, I could give you a ton of anecdotes about women who refused to settle even in the face of social pressure, desire for a baby, loneliness, and more, instead focused on their career/home/goals, and went on to find amazing relationships in their 30s and 40s, have healthy babies, and thrived because they stayed true to what they wanted and deserved. I could also share stories of friends and colleagues who raced into marriage in their 20s/early 30s to someone that seemed good enough for fear of being alone, only to have stunted their own personal growth and development, uncertain of who they are and what they really want in life, and end up divorced in their mid/late 30s, forced to now figure out how to build a life. It might help to know that NO ONE HAS IT TOTALLY FIGURED OUT. We’re all just winging it, though you’re doing an amazing job AT SO MUCH. Lastly, know that you will be okay NO MATTER WHAT. We’re all here for you. I am sending lots of love and encouragement to you (and Jacob). You’ve got this.

  137. Lisa Amidon says:

    You are a “keeper”! Be proud of where you are in life. As for your goal of being a mom, you are in a bit of a “test” situation now without the daycare expense. To me, your boyfriend is your man child. He should be doing all the house chores as he currently has the time, rather than you taking care of him. Unemployment happens to all of us at some point for whatever reason. Pitching in more in other ways during this transition is reasonable. Since you are not married, put yourself and your goals first. If you do marry, a plan of action should be put in place so that you both actively participate in achieving a mutually agreed financial goal. Equally yoked is a foundation worth striving for. Right now, you may need to set down boundaries. I wish you the best in whatever you decide.

  138. Tanja says:

    Dear Olivia,
    you already know the answer. You ALREADY know the answer. Sending love to you!

  139. Susan says:

    Hi Olivia-Congrats on getting so far, so fast on your financial journey! I haven’t read EVERY comment, but it case it hasn’t been mentioned, your mortgage will often have a minimum amount of time that PMI must be paid. Check your paperwork. 🙂 All the extra payments may be for naught (versus another use) if you have such a provision. My only other thought would be that being on the same page financially is a constantly evolving conversation. My spouse and I are 10 years in and it is still a process. We came from different families with very different attitudes about money, never mind law school debt. Spending time to sort things out financially before you are married is much cheaper and a lot less heartbreaking than divorce. Best to you on the next part of your journey…..

  140. Rebecca says:

    Hi Olivia, I am so impressed that you have managed to buy an affordable home in what sounds like an awesome community in suburban DC! That is huge, and your substantial savings are impressive. I think on the financial front you are doing awesomely. That’s the positive part : ) And yes, a PhD sounds like a great path for you.

    I am also super concerned about Jacob. I work for a family medicine residency program. Getting fired is only a last resort outcome and the fact that they did it at 11.5 months instead of 12 months speaks of some serious issues. Sounds like they felt he needed to start over as an intern or they were so fed up with him they wanted to make sure he didn’t get into another program. We do everything possible to root out issues early on, residents who are struggling wether they are academic or behavioral issues get put into a structured support system. There is constant dialog and discussion with them. I am currently part of a structured support program for one of our residents, they are carefully tailored to the specific issues and the goal is for them to succeed. The only way someone would be fired is for them to have been not wiling to work on issues, not willing to work with others and having really egregious behavioral issues. I can only imagine it happening in the setting of significant mental health issues and the resident refusing to get help. I know we don’t have much information here, but I immediately was alarmed that this is more than just ADHD, that he may have a personality disorder as well. Honestly, a personality disorder is one of the only scenario’s I can imagine that would create the behavior to get kicked out of residency. Go read a bit about them and see if any bells go off. I would be very worried that no other residency will accept him. Those openings are mostly from residents deciding they want a residency with a different focus or one that is a better fit for them.

    I do also want to throw out there that our culture still finds it very unacceptable for men to not work. I think the responses would be different if the roles were reversed here. My husband doesn’t work, I have a high salary and demanding job, he’s a “house husband” and it’s fantastic! Was hard for him at first, it’s a long story how it came to be, but it works really well for us. But people are really not accepting of it. He has a couple of side hustles he does and I just tell people that’s his work.

    And lastly, do ask your family for an honest opinion. They will probably hem and haw a bit at first, but try to get them to be honest.

    I wish you the best! Hope this turns into a turning point that leads to a fantastic future for you!

    • Mary in Maryland says:

      Being fired at 11.5 months indicates that the residency program thinks Jacob should not be practicing medicine. Licensure usually requires having completed an internship. Jacob is not going to be working as a doctor.

  141. Rachael W says:

    Hi Olivia, sounds like you are doing great financially! So happy for you, keep up the good work. It sounds like you have your head on very straight and eyes open to the world around you. I never heard of this co-op thing and will definitely have to look into it in the future. Couple things that gave me pause, Jacob getting fired and being unemployed extended at the moment. I really hope that he lands another residency and that you two can continue a successful relationship where all goals are met. However, I would strongly encourage you to look at his history of his employment. I met my ex-husband when I was 21 and he was 35. At the time he was not working but had a settlement from a workers comp case. In hindsight this was a huge red flag. Fast forward to our future marriage and two kids and to today, he has a pattern of working hard for 2-5 years and then not working for 2-5 years. This has put immense stress on me and I have provided 100% of care and financial support for our 2 children for the majority of their lives. If Jacob is 36, he should be old enough to figure life out and have some history of stable employment. I understand that medical school can take a long time to complete and I have a few friends in these fields, but I would be very weary of getting married to this debt and possible history of unstable employment, particularly with you being so strong of a go-getter. Mixing a person who goes in and out of employment with an overachiever can cause huge resentment down the road, throw in a couple kids and things become toxic quite fast. Also consider having very frank conversations on who will be doing what, in regards to child rearing before actually having any children. Do you both plan to work and put the child in daycare, will there be alternate schedules to cover child rearing by only the parents, will someone not work, who takes sick leave when the child can’t go to daycare, etc. It sounds like right now you are in the thick of it, I think you should encourage him to get a residency ASAP and if that is in another state, so be it. Long-distance relationships can work and the distance would give you clarity and decrease any current co-dependency that may be present. I would also add that if you were married and one spouse stops working, then a divorce ensues, the person who continued to work can become liable for spousal support. Not to be too negative, but just some important insights that I learned a bit too late. Best of luck to you in your financial future!

  142. Kathy E. says:

    My 2 cents : Consider – Is this the Right time, right place and right person ?

  143. Chris B says:

    Dear Olivia,
    I fear you’re buried in comments and not reading anymore 😉
    You are a Star and remind me very much of my dearest, oldest friend. We are both from the DC area, and I know that what you’ve achieved for yourself is simply stellar. Your prospects in that area will only grow better and more lucrative…please do heed the advise on putting boundaries on your work schedule and checking on your market value for the skills you have. I have found that making my time limited increased my recognized value at work greatly, and I was able to guard my free time well. Shockingly, the company did not collapse. As someone else said, everything always is urgent, which means that none of it is urgent 🙂 Heck, they probably missed the truly urgent item whilst clamoring for the rest.

    Back to my friend. She was in her 30s, in a relationship with an MD in his residency. Like you, she was the BEST, fun, and generous. Like you, she had dated, but no serious long term relationships that ever “stuck”. Lo’ and behold, ERIC enters the picture, with all the luster and status and parental positive nods that go along with “oh, she’s seeing a doctor”. Right. Marriage was discussed, it was “serious”. His family openly was “well-off”. Hers stayed humble, even though I believe they’re multimillionaires now.

    My friend always accommodated his schedule, his preferences, his temperament. His work was so critically intense and stressful, and she “only” was a teacher and would never make much income. He lived way beyond his means -glamorous, maybe, but I bet that dude still is in debt to this day. Vs she quietly squirrels away modest amounts into her growing retirement accounts. Anyhoo- it was always about his family, his social engagements, his schedule. She dropped so many of her usual life for him (NEVER EVER a good strategy, ladies!!).

    If he accommodated her, it was cause for applause and praise, so great was his achievement (sarcasm). Turns out, Dr Eric made her feel like crap, in many personal/intimate ways and she had to twist herself all up to meet his needs. It was awful to watch. I don’t remember the cause exactly, however thank goodness he did something to make her angry enough to break up with him. Amazingly, he found a new love and was married within a year. She once more became happy in her own self, with a full life and no one to shape herself around who didn’t do the same for her.
    Yin and Yang – BOTH people fit. Not one pretzeled around the other, who says that he’s just trying so hard, blah blah blah. It creeps up on you! Please get some space and remember who YOU are.

  144. Chris B says:

    P.S. I think this is the most emotional comment stream the FWs have had for a case study. Clearly Olivia’s situation hits home for many of us.

    • Sophia Kitts says:

      Yea it does. My dad was a Jacob. He sold my mother’s jewelry (her grandfather was a jeweler) rather than work to make rent. He was so good looking and charming too.

  145. T says:

    Olivia is right on track and is doing an outstanding job with her career track and finances. As much as she loves Jacob getting married could shipwreck her life and destroy all of this. I am sorry to say this, truly I am. She is 31 and IF she wants children of her own there is no way she can take on Jacob as a spouse and father of her children.

    If, he is accepted into another medical residency and is fired yet again, what is next? One may be academically gifted to become a medical doctor or whatever it is he is seeking BUT, that does not mean they are psychologically fit to do so.

    If, she is willing to take on his debts and the liability of him potentially never being able to get a job in his chosen profession, or hold down a job that pays a decent wage/ salary due to a psychological disability, AND forego children, AND let the house go AND downsize AND does not mind massive debt without an equally stable and successive spouse then this relationship would/might work.

    Jacob needs a lot of financial support, in excess of what she can provide without living in a tiny house on a rented space not to mention professional therapeutic help to enable him to get and maintain some level of enjoyment.

    If, she loves him so much that she is willing to pull the plug on her own goals, achievements or having children, then she should do whatever will help him. But, she could sacrifice everything for love and wind up destitute, with a wrecked career , credit score and massively in debt and in utter financial ruin.

    She is not wealthy enough to bail out Jacob and support him for life. Nor can she be his salvation.

  146. T says:

    Sorry, should read employment, not enjoyment.

    I really do wish the best for you Olivia.

  147. T says:

    Dang it. Found another mistyped word. Should read stable and successful

  148. Triton says:

    Switch the genders, and the roles.

    Would the comments be drastically different if Olivia was the one who was struggling with residency, enormous loans, and unemployment, and had a partner who was financially stable, employed, owned his own home, had a plan for early retirement and was ready for parenthood?

    Yes. It is not uncommon for a man to be the financially sound partner and a woman to be less solvent, and for a relationship to work happily in that circumstance. I’m the (female) one with student loans that I am nearly finished paying off, 10 years into my (hetero) relationship. I have paid every penny of them myself, and I was the one who was unemployed for a year. I have always contributed to the household, but, maybe not as much as I should have during unemployment, because I was depressed and stressed and figuring myself out.

    But hold the reversed genders scenario in your head. Would the comments be drastically different if Olivia, hundreds of thousands of dollars in debt, struggling with residency, ADHD, and unemployment, also casually mentioned that she would expect her rooted, stable, employed boyfriend to sell his house in a neighbourhood he loves, to follow her to residency across the country, compromise his own well established career, move away from his family to be closer to her family, delay or give up his own PHd program, and invest in her family’s vacation home because she’s emotionally attached to it…and that he should take on primary childcare while she figured out a second residency program?

    No, they wouldn’t .

    Relationships can be, and often are, incredibly financially lopsided, but that is an insane thing to ask or expect of anyone. Insane. And yet.

    My husband immigrated to a different country for me. There is no other reason. He left his family in Finland, where he had recently graduated, in one of the best, most well balanced across the board countries in the world, to come to Canada, where his credentials meant nothing. He has spent the past three years re-taking exams (passed the last one last week woo!) so that the Masters in Engineering he completed there will be recognized here. His career prospects have been delayed, he spent tons of money to immigrate, he spent some of that time finanically supporting me when I moved provinces (school is free in Finland and he has Euro’s!), and spent years here working retail and in the toursm industry, all in his third language (Of four. His competance is both irritating and impressive).

    His career has been delayed enormously. His retirement is all shot to hell because this is not a socialist country and we have to do it largely ourselves and he has no idea how Canadian financial systems work.

    Olivia, this is important. It is enormous, with impacts and consequences that will follow you into your eighties and nineties, and impact whether you can afford to pay for your children’s education, and whether you can pay for a good nursing home for yourself.

    We knew all that, too, or at least I did. I grew up poor, and my mom lives with us because she had no financial plan for retirement. I had been planning for that since I was nine, knowing I would be her retirement plan.

    The point is, it didn’t matter. At all. We couldn’t *not* be together. The financial hit is real and impactful, and totally, completely irrelevant. We were long distance for four years, and one of us had to move countries, because we couldn’t *not* be together.

    2/3 of all of my (enormous, Italian) family members are divorced, one acrimonious divorce has lasted over 7 years because of …you guessed it…money and investments. I knew the risks, and every step along the way, just like you, I plan for the fact that at any moment, one of us could just up and leave, even though we are married now (got around it a couple of years ago). You’ve gotten yourself to this point. You could do it again if you lost everything and needed to. Nothing is guaranteed. I have to be financially solvent enough to take care of my own retirement, and my mother’s last years, entirely on my own, just in case.

    But we couldn’t *not* be together. So we are together, finances be damned. We visit his family when we can. I contribute to the household equally now that I can (I now have an excellent career, but it took time), and every spare penny I have goes towards my student loans. It’s hard, but certainly not impossible. We have a house, we own a car. We won’t be having children, but if we did want them we could have them and give them a good life.

    The tradeoffs were worth it, a million times over. It’s not “just money”, it’s the whole shape of your life, and your security as you age. And also, compared to the shape of your life…it’s just money.

    And it would never, ever have crossed my mind to write into Frugalwoods and ask if it was a good financial choice, because it was the *only* choice, finances be damned.

    Is that the kind of relationship you are in?

    • JB says:

      You make an excellent point. Gender roles are certainly at play here but it goes beyond that. I think it is easy for us readers to go with the face value story, tone and discouraging examples from the writer here. Her doubt about the relationship was hard to miss, and it’s difficult not to jump to her rescue.

      How interesting if we were to have heard from Jacob. Firstly, is this even how he’d write the story? Wouldn’t it be something, if, in the future, Jacob himself were to write in a case study from his perspective and no one knew. Might there be a perspective in which we’d rally around HIM, a young person who has always struggled… finally getting into medical school at huge expense financially and emotionally. Then messing up somehow and it all comes crashing down. A person who writes in at the end of their rope because it never seems to work out and the debt and disappoint continue to grow. And the only bright spot is a wonderful but doubtful girlfriend who is willing to give him a chance, for now. Wouldn’t we be encouraging and cheering for him to get out of debt, makes steps in his schooling and career, and gush over the wonderful partner of his who stands by his side? Haven’t we read case studies before this one from someone seriously struggling and no one wrote in to say “You’re such a mess ; your partner would be wise to leave you. You’re obviously trying to ruin her life.” While the comments urging Olivia to think twice about the relationship may be wholly wise, it doesn’t mean that Jacob doesn’t need just as much of our support.

      I really, truly can’t wait to hear Olivia’s update someday down the road. I suspect many of us already know how this will go, but, I’ll admittedly be glad to read it, if Olivia and Jacob surprise us.

  149. Jane says:

    Dear Olivia, I don’t have advice for you. Just a question for you to think about. If a friend were in your situation, what advice would you give them? It’s easier to be objective about others in ways we aren’t for our own situations. I’d listen to friends and family too. They know you best and should have your best interests at heart. What ever decisions you make there will be tough times but it always gets better.

  150. Laura says:

    Another thought I had: my son’s college girlfriend of 6 years dumped my son when he could not find a “professional” job in 2009/2010. She got a job right out of college as a teacher. He was looking for something in national security. The Great Recession era. Little hiring being done. He did get a job at Barnes & Noble and was contributing to their joint finances (but not as much as she was). In any event, the girlfriend’s constant disappointment with my son was not helpful. She kicked him out of their place. Along comes my son’s friend at Barnes & Noble who saw the good in him, picked him up off the floor and loved him, making it possible for him to eventually become the software engineer and manager he is now (with a fortune 500 company). They have been married 6 years now and have a child, 2 years old.

    I told my son that a woman who will be with you during your deepest, darkest times will be with you the rest of your life. I love my daughter-in-law for seeing who my son really is and not just focusing on temporary problems.

    I agree with others who have said your guy must be smart to have made it through medical school. That’s no small feat. And physicians do tackle their loans over time. There are ways to make this work if you both love each other. He does need some medical support though as a psychologist mentioned above and as I mentioned too (a note about how functional medicine can help ADHD) in an earlier comment. Best wishes!

  151. Mary says:

    I see lots of red flags here. Olivia, you are responsible for yourself. Not Jacob nor his financial situation. Do not take his problems on as yours. They are his problems. This is what screams out at me in reading your story: his problems are not yours. Personally I would not make a life decision until his problems are resolved. Currently, Jacob needs to find a job to contribute money to the household. He needs to step up, and you need to remember you are not his mama bear, taking care of him.

  152. Jamie says:

    My main suggestion is to make no irrevocable decisions anytime soon. Do not commit to Jacob until you see how this plays out. If he gets into a new residency program, go long distance for awhile to see how it goes before you even contemplate moving – what if there are problems again? Not an unlikely scenario if he didn’t do much work figuring out how to address his part in the problem – dictation software won’t be enough to fix attentional and processing issues without the help of meds and/or cognitive-behavioral training to learn new strategies. Discuss timelines with him – how long are you both ok with this status quo while waiting to get into a new program? When does finding work or coming up with a new long term strategy come into play? And DO NOT wait to have the important conversations about the future – if he ends up working in a rural area, are you ok with moving when it could severely impact your career? What are both your thoughts on the timing of kids when you both have educational goals that require intense time commitment? Where do you see yourself living long-term and how does that align with BOTH of your goals and desires? In your write up, it sounds like you have made, and plan to continue to make, all the compromises. That isn’t sustainable, so I think now is the time to figure out how he handles real honest conversations about what might require compromise on his part. Love can overcome a lot of problems and most things are fixable, but only when the effort is there on both sides. Make sure he’s putting in the effort too.

  153. RJ says:

    Olivia, I haven’t read all the comments yet but you are freaking awesome!
    I wanted to share something from my life: I have adhd, involuntarily took a voluntary separation from a job, hired a lawyer to help me navigate that, and kept on doing basic life tasks (which for me at that time were paying rent, buying groceries, planning food, saving money, going to the gym).
    I am a woman who dates men. I highly doubt a man would make the same allowances for me that you are making for your partner.

  154. Jenna says:

    First comment one this site but a long time reader. I’m French, living in Paris in France. and our life is very different… But, I think we as human beings are not that different. I’ve read almost all the comments. And what pushes me to comment now can be expressed in a word: narcissicism? With a question mark. In Europe, ADHD is not often a subject, except for children and in very extrem cases… I wouldn’t say we, europeans, are right with this. But, I can’t help thinking that the « tag » ADHD can be very comfortable for an adult unwilling to assume their part of work and responsabilities. Never forget a person can be very nice, attractive, seductive and… driven by their personal interest. I know it can seem harsh. But, I have experienced it, although the circomstances are completely different. After more than 20 years of marriage, I suffer right now from a very difficult divorce. Believe me I regret to not have perceived or at least understood the red flags.
    I have heard of stories of spouses working very hard during a long long time to make the family live… and been left with the children and a « nice story telling » when the effort is done! Narcissists know how to manipulate others…
    I don’t say it is the case here. But I feel pushed to write this comment…

  155. Stacy says:

    Hi Olivia,
    What a brilliant, wonderful future you have! Bravo!

    I will not add much to the advice regarding Jacob, except to say it can be done, will not be easy and will take work from both of you. I have been married to an attorney with ADHD for more than 30 years, have two brilliant, talented children with ADHD and one with autism and Tourette’s. I have a background in finance as well as teaching and a special certification to work with special needs students. Success counseling is essential and bottom- line: Jacob must admit that he requires assistance with his issues and you and he must both commit to this hard work. Our therapy and training was essential and I unsurprisingly am the more structured one in the relationship. People with ADHD can be awesome: empathetic, entrepreneurial and insightful. Pharmaceutical sales, teaching, and even therapy might be options for any alternative employment. He most likely would make a lousy stay- at home dad, but that’s ok. One option for meals is to cook together on the weekends ( refrigerate and freeze). It can be fun and romantic.

    Now for your finances. I would watch putting too many funds into this house as I doubt this is your “ forever home”. Think about that. Instead, as you have been advised, put the funds into a brokerage account. Mrs. FW has great advice on getting started in that arena. Index funds are great. You want some nice dividend paying stocks! I would take funds and also put into lifestyle so you can visit Jacob if he moves for a new Residency or career. Also, who inherits your property should something happen to you? Do you have life insurance, disability? I would at least have enough life insurance to cover the loan balance.

    Questions: You don’t mention a budget for fuel, car maintenance and repairs or the specifics of the food budget even though Jacob provides that. You two need to discuss that. Perhaps you need to know what the groceries are costing and if he seeks employment he could help with utilities, WiFi and some transportation costs, up the grocery budget and help with lawn expenses? Could his parents help with therapy, attorney fees to help with reinstatement (employment attorney needed, I believe) ?

    Anyway, when one is in a relationship I know it’s not “ I”; it’s “ We” . Best of luck in the future!
    You’ve got this!

  156. Chris says:

    Olivia is in great shape financially. The sticky point in her life appears to be Jacob. The relationship is asymmetric, Olivia provides, Jacob takes. He managed to get himself fired from a residency program (not his fault, it’s ADHD), doesn’t pay for rent or food ( not his fault, he is unemployed), can’t contribute to the household upkeep ( not his fault, he needs to apply), and needs to buy his families vacation home (not his fault, he is so emotionally attached). That’s many red flags, and Jacob might become a high and long term financial and emotional liability.
    For any course short of moving Jacob out of Olivia’s house immediately, I believe Olivia should consult a lawyer re her financial obligation for Jacob’s past, current and future debt, and potential responsibility originating from her cohabitation with Jacob which establishes a marriage-like association and in some legislations results in financial responsibility for the roomies purchases etc (think roomie buys Porsche and has it delivered to house, you get bill)-I’m not a lawyer, but these are questions I’d want to clarify fast.

  157. Sandra says:

    26,27 years old would be around the correct age if Jacob went straight through college and then medical school. He’s 36 years old now and I’m assuming he went to Medical school later in life. What was he doing for those unaccounted ten years? Was he in a field related to his bachelor’s degree? If so, perhaps he can get back into that line of work or find out if he can use his medical school
    credits/challenge a state exam to become a physician’s assistant?

    apply for a physician assistant position?

  158. Lena Pinnel says:

    Hi Olivia, your case study sparked enormous amounts of reactions 😊 I haven’t read all of them but I just wanted to add something positive to this conversation because I’m sure it’s been hard enough already. I wanted to let you know that I have been with my guy for over 7 years now, and when we met, he carried some debt. I knew about that and we worked on it together. I never payed his loans, but I stood by him. Because he was so in debt, and because he had known so much stress financially, he didn’t care anymore. Over the years, under my influence, his attitude started to change and he became more mindful about money. When we were expecting our first child, we sourced everything second hand and he decorated the room for almost no money.
    I used to be stressed out at the beginning of our relationship because we had both been single for a long time and it was hard to adjust. It took us a couple of years to understand each other – how we worked, what we needed, what we want out of life. I don’t really believe in the prince charming story: I think every relationship requires work, some more than others. I have seen him become a wonderful father to our daughter. He is actually less stressed out having a kid – he enjoys life more. I might do more of the household chores, but he will be the first to take her outside to the park so I can have some time on my own.
    So. People evolve, they grow, they change. I wish people wouldn’t judge so quickly about a relationship 😊 Also, you are in a position of strenghth: you have your house, your job, your savings. You can do whatever you want and that is comforting. Best of luck to both of you, you can do this.

  159. Katja says:

    I would want Olivia to focus more an her selfcare:
    Yoga, gone with the bought house and the occupied room – find a way to re-install it in your life.
    Food: ok, we all feel like ramen sometimes. But this is the worst way to save money long term.
    Please don`t sacrifice in these areas. Health is important as you age and if you still want to enjoy live.

  160. Abigail says:

    Hi Olivia, I am late to the game with this comment. I’ll leave the relationship comments to others, but assuming you and Jacob are staying together I think you need a game plan for what happens if he cannot become a doctor. You wrote, “The worst case scenario for my financial life is that Jacob moves to another part of the country to finish his training.” But what happens if he isn’t able to finish residency and is left with his NHSC obligation? It’s sounds like you’re pretty aligned with respect to frugality, so if Jacob does finish and go into practice, I bet you two will be able to come up with an aggressive timetable for paying off his debts even if you are in a long-distance relationship while he’s with the NHSC. To me, the biggest question is how you tackle the scenario where he needs to completely rethink his career choice. Are you prepared to financially support both of you if he has to start over?

  161. Steve says:

    If Olivia is serious enough about Jacob that she would consider marriage with him, I would commit to the extent he is willing to commit. What I mean by this is that he has some very significant debt, and zolivia is very, and rightfully, concerned about it. I would make sure that Jacob is well aware of those concerns and then see what his feedback is. As positive feedback is reflected by him, I would increase the amount of effort I gave him. He has to show progress in order for me to give more effort towards further progress. But in no circumstance whatsoever would I pay for his debts. That is his responsibility. imo. As things grow (while the debt shrinks), I would slowly dip my toes, then feet over time, into growing the relationship more seriously. But, again, he must show his interest in bu8lding the relationship by his actions to do so.

    I wish you the best, Olivia.

  162. Beth says:

    Hi Olivia.

    I am a female physician 2.5 yrs out of residency. I had $290,000 in student loan debt when I graduated from residency and I have $115,000 today. So the debt doesn’t really scare me. A physician can work hard and crush the debt while also building toward retirement. I do have 2 kids under 3 yrs too! (But also importantly, a husband who brings home a lot of bacon too).

    My main comment is the same as the other physicians above. The termination from residency is a huge red flag. This is extremely extremely rare. This sounds insensitive but there is a right of passage in just “sucking it up for X amount of yrs” just like everyone else who became a physician did. Lots of other people with ADHD made it through. Why didn’t he? And call me old fashioned- but it should be really really hard, we are responsible for human lives!

    You deserve someone who is scrambling in this situation to make the best possible outcome happen. In my opinion you should not be playing the mommy role. Too many women are falling into this trap these days. Demand more.

  163. Jane says:

    Dear Olivia,
    I am a doctor and will mince no words: it is hard to get fired from a residency program and it is a huge red flag to the next program director. Without a completed residency, he cannot practice medicine. This is the reality of his situation. Think long and hard before hitching your horse to his wagon.
    Best of luck to you.

  164. Allie says:

    Hi Olivia, I’ve never commented on here before, but your case study rang alot of bells with me, so here’s my two bits to think about..I’m also a chronic overworker with a partner who has a mental illness, so I can sympathise with where you’re coming from. And mine is an amazing guy. But he would never have asked me to do some of the things Jacob wants of you, and I worry that you won’t stand up for yourself on the important things like finances and childcare. We did 4 years hard graft in couples therapy to work out the kinks (totally worth it) , but you have to know this; fundamentally, they will not change. The Jacob you have now is the Jacob you will have at 60, at 80, etc. So good luck with whatever you decide to do, and please lean on your friends and family for support; it’s hard on you both if you are each others’ only lifelines. P S awesome work on the finances! ,

  165. V says:

    Hi Olivia, thank you for being so open and thoughtful about your situation. I just wanted to comment from a different perspective, one that is more considerate of Jacob. Both my father and my brother have ADHD, and it’s really impacted their respective financial lives and relationships. It’s been hard to watch, because they are each such good men. My stepmother stuck with my dad despite some super challenging periods, and my perspective is that she thinks it has all been worth it. Both she and him came from very traditional gender roles that neither was looking to move out of, but over time they realized that the best way for them to play to their respective strengths – and be able to enjoy each other – was to switch it up, with my dad doing most of the child-bearing and cooking and her holding a job down. He was fantastic at this role; super late sometimes, and always losing keys and what-not, but the most fun and loving father to us. Same with my brother – he excels at caregiving compared to most guys his age, is amazing with people and has so much to offer in a relationship. But is just too scattered and disorganized unfocused to do well career-wise.
    All this to say that I think there are ways through this crisis if guys work together honestly. I strongly suggest counseling, either together or on your own. Maybe a financial counselor too for the both of you? This just a quick thought, but perhaps Jacob’s role could be to earn enough doing whatever just to pay his debt within a reasonable time frame and to have his own modest spending money, with the agreement that he effectively becomes the house-husband (this role assumes that he wants kids too). You guys could easily draw up a pre-nup that protects you from his debt. Having kids creates huge pressures on a couple for finances and time-management anyway, so the two if you would basically be just front-loading some of those issues.
    I think the goal for a strong relationship is for both partners to feel loved, respected, and appreciated for their contributions. That doesn’t have to be “spreadsheet equality” for each task and responsibility. I do all the money management in my marriage, for example (my husband hates it) and there is plenty that he does that I blissfully don’t have to deal with, but we both feel good about what we do. I think it’s worth trying be creative with Jacob if you want to be with him.
    Also, I’d suggest that you have a kid before diving into a PhD. I got my doctorate while having babies, and if there’s anything that muted my love of learning it was sleep deprivation! The degree became a life sentence while dealing with babies and toddlers. I’m glad I accomplished it now, but I honestly might have enjoyed my kids’ earlier years more with a regular job and a more stable/predictable work routine.
    Lots of love and respect to you – your thoughtfulness and kindness is inspiring!

  166. Jen says:

    Hi Oliva,

    I’m a bit late on the comments chain and wasn’t sure that there was anything that I could contribute that hadn’t already been said, but I’ve been thinking about your case study all weekend and I think that there are a couple of things that haven’t been covered and might be useful for you:

    1) There have been a lot of comments about whether or not you will be responsible for Jacob’s debt if you get married or if he pays rent on your home and I think that a lot of folks are sharing from second hand or specific personal experience which is valuable but may be inaccurate. I STRONGLY suggest that you find a lawyer that you trust and have them explain how *exactly* your financial life will be tied to his if and when you get married or begin to more formally live your lives together. Only a lawyer can give you a full picture of how this scenario could play out. A good friend of mine just ended her ten year marriage with a doctor who recently ran into some trouble at work and the final nail in the coffin for her was when a lawyer told her that in the state where they live, she would be responsible for the thousands of dollars of debt that he had racked up on recent car and alcohol purchases PLUS his med school loans. She had no idea and will be paying for his bad choices for the rest of her life. If she had known the legal and financial consequences of remaining married, she would have gotten divorced much sooner and saved herself a lifetime of HIS debt. Consult a lawyer ASAP to get a full picture of your financial future with Jacob. Don’t leave it to advice from well meaning people on the Internet.

    2) There has been a lot said about leaving your relationship and I’d be lying if I said that wasn’t my first thought, too. Things are not always that easy, though, especially once you are living together. If I could have given you advice a year ago it would be to avoid moving in together because it increases the inertia that makes it hard to end a relationship that isn’t *bad* but that has its potential red flags. Years ago I was in a similar situation (loving relationship with someone that lost their job and was going through a personal/financial crisis) and while I knew that I had some very real concerns about our future (and the financial and emotional responsibility that I would have to take on if we stayed together) it really felt like breaking up with them or establishing stronger boundaries would be like kicking him when he was already down. NO ONE wants to make a loving partner’s life worse when they are already at rock bottom. My finances suffered for a while because I wanted so badly to make them feel loved and bring a little bit of joy into a very stressful situation. He was, to my mind, a very frugal person in that he didn’t buy lots of new clothing or gadgets, but I looked the other way when he paid for “experiences” that we could do together or gifts for me that I neither wanted or needed because “he’s going through a hard time and it’s not THAT expensive and it would be hurtful to turn down a gift”. Mentioning that the money spent on gifts could have helped to pay down his debt made me feel like a mean nag.

    The narrative surrounding that sort of situation is difficult to shoulder (breaking up with someone going through a hard time) and can make you feel like a monster but you sound like a responsible, pragmatic person who understands that even if there is so much *right* about a relationship, eventually all of the *wrong* or worrisome things could eventually create too much tension to sustain you in the long run.

    3) You mention that you and Jacob have good communication which is so important but I did wonder: does he know that you wrote this post on Frugalwoods? If so, what are his thoughts? If not, why didn’t you tell him? What would you do/feel if he found this post and identified that it was you (I’m assuming that you used pseudonyms, but I could be wrong)? Asking close friends or family for advice on a personal matter is one thing, but reaching out on a very public financial forum is another entirely. Communicating is important but being forthcoming about your relationship concerns is also important if you want your relationship to survive the challenges that you currently face. If you wrote this reader case study without his knowledge (especially given the very concerned, overwhelmingly negative and probably justified responses in the comments), that would be one of the biggest red flags that I see for you. There are, of course, many benefits to crowdsourcing advice on the Internet, but it will tell you a lot about your relationship if you hope that he never reads it.

    Contempt is one of the biggest predictors of divorce (further reading: and many of the things that you wrote in your case study sound as though you don’t trust him to manage his own legal, financial, and employment issues…and perhaps you shouldn’t. Do you feel like an equal partner or more of a caretaker or parent figure in your relationship? You are obviously really good at managing your own life but that doesn’t mean that you don’t deserve to be with someone that can manage themselves as well.

    I don’t think I’ve ever had so many strong, personal feelings about a reader case study before and I sincerely hope that everything works out for both you and Jacob. <3

  167. Therese says:

    If you’re still reading, Olivia, here are some facts and thoughts…
    You went from independent, secure, relaxed to having to mother, financially imbalanced due to Jacob not contributing, and stressed. He also comes with a >200k baggage that he hasn’t been repaying guessing since unemployment.

    The unknown is, when will he get sorted with his job and pay off the loans? And will you not feel resentful this whole time? Sometimes love just ain’t enough. But there’s also the saying that love conquers all. You are the decision maker in this case.

    He pays groceries yeah of course, but how much do you eat anyway? And no breakfast and lunch for yourself? Please don’t do this to your body because it causes more harm than you know. You won’t feel it at 31 but soon enough you will if this continues. Healthcare is very expensive in America so please don’t add more stress to yourself by taking care of yourself now.

    Being unemployed or ADHD or having huge debt is not a crime. And I’m sure Jacob is a very likeable person otherwise you wouldn’t have fallen for him. What we readers are commenting here are more for your own sanity and happiness because many of us have been there done that and really wish you didn’t have to go through it.

    If I were you, I would ask Jacob to move out and he can come look for you again when he pulls his shit together. By the way, slowing down and noticing the views and flowers during hiking? ANYONE can do that including yourself, it’s called awareness of the surrounding, or slowing to smell the roses. It’s great he gives you the idea but… you know it deep in yourself you’re just not executing it… yet?

  168. Meredith says:

    FWIW, as a DC resident, the $87 car insurance bill doesn’t strike me as too odd for the DC area. I shopped around quite a bit for my insurance (also on an older car, although worth more due to lower mileage), and the absolute cheapest was right at that price point (even with discounts for being a government employee and driving relatively few miles per year). I’m a female around the same age as her, with a clean driving record, so it seems like our profiles would be pretty similar.

    I read an article recently that some insurance company had rated DC-area drivers as some of the worst (e.g. most accident prone) in the country. My personal perception of the traffic around here matches that rating — lots of people from all over the country and all over the world (with different ideas about how one should drive), driving on crowded roads, with lots of strange traffic patterns (multi-lane traffic circles, highways with a ton of weird merging, etc.). I have a feeling that the relative riskiness of the roads that we drive on in this area are probably a big contributing factor as to why we pay more for insurance.

  169. Finally Frugal says:

    Olivia, I’ve been a Frugalwoods reader for many years but never never moved to comment before – until your story hit so close to home.

    I don’t believe my husband has ADHD, but he shares many similar traits – and added major depression to them after losing his job a number of years ago. I was the sole support of our family for almost 6 years during which he wasn’t able to be the wonderful partner who takes over all of the home/childcare without being asked (I hope the commenters who experienced that know how very lucky they are!) But, with a lot of therapy – both individual and couples – we were able to make it through some very tough times and end up a loving and committed couple. And get him back to work! We’re probably happier and more committed for having gone through that time – but it’s hard for me to say that I would have chosen to go through it if I’d had the choice.

    I hope what I learned in the process could be helpful to you. A real turning point for me came when I realized that I couldn’t keep waiting for him to “fix himself” so that we could resume planning our life together – I needed to start planning for my life on my own even though I intended to keep him in it. We had put so much on hold when he lost his job that I just had to pick up by myself, because waiting for him to be ready to plan for the future could have taken forever. How would I plan for retirement, how would I provide for our kids’ education, how could we afford a larger house, how could I reduce my work hours to have more time with the kids? All of that was mine to figure out on my own. I couldn’t “fix” him and he might never “fix” himself, but I could plan for what I wanted in my life without leaving him. And I did. I got frugal, changed our lifestyle, focused on my priorities, and improved our financial situation to the point that I was happy with where I was in life, even though he was still struggling to be happy with where he was in his life. Making and sticking to a financial plan is much easier to do with a like-minded and supportive partner – but you are already doing it all for yourself and doing it beautifully. So I would just recommend that you hold onto your plans and priorities – whether or not you stay with Jacob.

    What do I mean by that? It sounds like you really want to do a PhD – and you’d like to do it full time. So focus on what you would need to do to make that happen. Not planning to do it if/when Jacob has a nice fat salary, but how you can do it no matter what happens with Jacob. If you took all of Liz’s advice on where to save more, how long would it take you to build up a cushion that would let you quit and pursue that goal? If you found higher paying employment, would that make the timeline shorter? What are you willing to do and give up to achieve that goal? What you’ve already achieved financially tells me that you could make a plan and make it happen.

    And you can do all that without ending your relationship with Jacob. You sound like a lovely, compassionate person and Jacob is someone that you care deeply about, so of course you don’t want to abandon him when he’s hurting. And you don’t need to in order to keep planning the right life for you. He might not be able to live locally for awhile? OK, so you do long distance while you stay in your house and pursue your PhD plan. If you stay together through the long distance and he wants to move to Vermont to be closer to his family? That might have to wait until after you finish your degree. Or maybe you could do it if you were at the dissertation phase. Just don’t let all of these what ifs lead you to spend time waiting to see where he’s going before you take action on where you’re going. Go ahead and plan for where you want to go with or without him. You’ll figure out whether or not he’s the one for you while you are both pursuing your goals in tandem. If it’s meant to be, it’s meant to be. But it’s certainly not meant to be at the expense of what you want in your own life.

    The one thing that has me scratching my head – your apparent acceptance of Jacob’s decision that “managing his current situation and searching for a new residency program is a bigger priority for him than having a small source of income.” As a frugal person, you know that any income that can pay down debt or be invested to grow for the future is worth it. I’ve seen your comment about how frugal Jacob is – which sounds like a wonderful match for you. But the decision not to pursue any income is not a frugal move. And it reminds me of where we were when my husband lost his job. I asked him to make a list of all the ways we could save money. He came up with the pretty standard stuff (get rid of cable, shop our cell phone plan, get rid of the newspaper, eat out less, etc. etc.) but then didn’t do any of it, because it was all “too small to make a difference.” How would saving $40/month by dropping cable make up for his loss of salary? At first I didn’t insist that we do anything he wasn’t willing to because I didn’t want to make him feel bad about losing his job. Then when I got frugal I did insist that we do all of the stuff on his list – and of course it did make a difference. I was kicking myself for not insisting that we do all of it immediately when we lost his income. And I think you might look back and kick yourself for not insisting that he apply some of his time and energy to bettering his financial situation (and perhaps contributing more to your now shared household).

    Only you know if Jacob is the one for you and you’re willing to go to hell and back with him. But if you choose to, I promise it will be easier if you continue to pursue your goals and priorities and don’t put anything on hold waiting to know where his life will take him. I hope this helps – you are obvious in my thoughts! and will definitely be in my prayers. May God keep both of you in the palm of his hand.

  170. Annie R says:

    Just wanted to say: when you’re in love, you almost always listen to people who agree with you and ignore a chorus of those who don’t. I have done it, too. I think of the line from the old Simon & Garfunkel song: “..a man hears what he wants to hear, and disregards the rest..”

    Olivia, if there’s any way you can force yourself to listen to the overwhelming amount of advice here, including Mrs. Frugalwoods’, please try.

    • Gaby says:

      Exactly what I wanted to say. I understand it’s difficult to hear the person you chose being criticized…because let’s face it…WE take the criticism personally (“you attack him, you’re also attacking me”). A lot of us get it. I had a friend who shut me out when I was too blunt with her about her relationship. Then she married him and filed for divorce not even two years later. Over finances and differing lifestyles and goals. She later admitted the red flags were already there before the wedding, but she was determined to “save face”. I wish women in that scenario would see ending a relationship not as defeat or failure on their part but as saving themselves and their future.

  171. Betty says:

    Olivia, if you’re still reading the comments on this post…

    I concur that Jacob does not seem like a good guy. Maybe you will turn round and tell me he is actually, and is the light of your life. But consider what you chose to tell us about him in your letter to Mrs FW. That’s how you chose to describe your relationship – in very ambiguous terms at best.

    I’m not going to tell you to dump him right away, but I am going to tell you a few things:
    1. He needs to move out for a bit. You don’t have to break up, but you need a break from living under the same roof so that you can see what your life is like without him always there for a bit. Do you get to yoga more often? Do you sleep more? Are you less stressed? Is it easier to meal prep for yourself? If he’s not working then he doesn’t need to be in your location. He mist know someone else in the world who can out him up for a bit.

    2. He needs to take the impact of his ADHD on you seriously. This looks like getting treatment and engaging with it fully. You should not help him with this. Yes, it will be hard for him to organize but that’s part of the test here – is he willing to work that hard for you?

    3. I do think you need a big picture talk with Jacob, and you need to ask him two crucial question. First, what is his plan for the next year? Second, what if he can’t find another residency? This will help you establish whether he is an optimist, a fantasist, or someone who just needs a bit of breathing room to sort his life out. Then ask yourself if you’re really OK with his answers. And if, in your heart of hearts, you believe them. The question of how long you’re willing t put up with things being exactly how they are now is a good one. Are you OK if he never changes?

    4. Read “Crucial Conversations”.

    5. Parenting is HARD HARD HARD. Jacob, I’ll be honest, sounds like the kind of guy who will be ” Fun Dad”. Is that what you want? Everything in your life will get worse when you first have a baby. I love my son to bits, but his first year would have been a terrible time to redistribute chores, work on our relationship, job hunt, study… If it’s not fair now, it sure as hell won’t be with a baby. If he says he’ll step up then, ask him to prove it by stepping up now – when you’re both well rested and don’t have a baby to care fror on top of everything!

    6. Good luck! You sound really responsible. It can be hard to be so responsible. Try to let go sometimes too.

  172. Zoe says:

    Olivia, my heart goes out to you. I’ve just read so many of the above comments and if I were in your place I would probably feel a bit overwhelmed by all of the advice and opinions regarding your path forward with your current boyfriend, Jacob. A lot of people are saying you should remove yourself from the relationship, because it doesn’t seem to contribute to your long term goals, and this is probably hard to read and causing you a bit of anxiety — putting you on the spot to make a decision, as it were.

    I’m thinking I could contribute a suggestion as to how to think about your relationship in the context of your life goals. So that you can move past your current uncertainty regarding Jacob and quickly act upon your new resolutions in a confident way, and feel immediately more relaxed, happy and excited for the future.

    I commend you so much for having such clear goals at 31. Not to mention your AWESOME financial situation. The clear goals you have outlined, both immediate (like yoga) and longer term (like parenting) are your bedrock and the basis upon which you can attain clarity in the present.

    I’m 34, and I have spent most of my twenties pouring my time in various relationships with guys without asking myself what the relationship brought to my long term goals. That was mainly because I didn’t take the time to outline clear goals for myself, probably due to low self-esteem, and I feel I lost a lot of time as a result investing myself and my time in relationships that went nowhere. You might believe, having been single for a long time, that being single is also ”losing time”, but if you do, I assure you that being in a relationship is no help at all unless it’s strongly aligned with, and nurturing of, you lifetime goals.

    So what’s actually important right now is to not lose sight of those goals of yours, and to envision in a very detailed and concrete way what a normal week in your happy life would look like. You might like to imagine such a week, day by day. It would probably include yoga several times, seeing your family that lives nearby, being appreciated and not too overworked at work, having a light bike commute, having peaceful nights in a quiet, tidy home in the full appreciation of a solid financial foundation and a clear schedule to financial independence.

    Once you have that firmly in mind, you can start to assess what is bringing you closer to your happy place, and what isn’t. Start with the day to day, considering questions such as : Now that I have Jacob in my life, is it easier or harder for me to do yoga several times a week? With him around, do I feel I eat more or less healthily? Do I feel concretely supported in my lifestyle preferences? (Fill in with other examples of what is important to you).

    If you’re happy that your day-to-day is much improved with him around, then you can also ask yourself questions about longer-term issues, such as : Will I enjoy financial independence earlier if I partner with him? Will it be easier or harder for me to pursue a PhD down the road if I partner with him?

    Committed relationships are called partnerships for a reason : they are an alliance of parties and in the right scenarios, both parties benefit concretely and in measurable ways. It’s important to feel romance and excitement, but it shouldn’t be part of the benefits measured, because it very well may dwindle over time, for one, and also, it’s something that tends to be over-valued in our culture. Movies, series, our cultural imagination — they all put this tremendous pressure on us women to ”succeed” in ”having a relationship” and even to the detriment of our actual day to day lives.

    I realize that what I’m writing might sound individualistic, but quite the opposite, it’s about making room for the right partnership in your life. Having the right partnership, one that keeps you energized and in your happy place, is a tremendous accomplishment that will make you able to inspire and support others, be a pillar of your community, and do good around you. (Shoutout to Liz here whose marriage and attenant blog is inspiring and uplifting thousands! I read in her book that it was Mr. Frugalwoods who actually set up the blog in the first place, as a surprise for her, because he knew she dreamed of writing and hesitated getting started. Now that is a benchmark of partnership we should all aspire to! ).

    You need someone you share goals and interests with and with whom you will resonate so strongly that you will be blown away by how exciting the horizon of life can get, how strong you feel, and how wide possibilities get.

    The only thing I feel you shouldn’t be considering as this point is whether it’s easier to have a child with or without Jacob, because you’re 31, not 41. You are in no rush at all. Should you break up with Jacob, you have ample time to meet someone else to have children with. So it’s not like your only choices are him or single motherhood. Quite the contrary, I would expect there to be a long lineup of men ready and willing to partner up with such a thoughtful, solid and savvy person such as yourself, especially when you start seeing yourself as such and showcasing your confidence and brightness in doing what you value, such as for example pursuing a yoga teacher training.

    Two years ago, my 2017 New Year’s Resolution was to value myself more in any future relationship I would have with a man, and to do so by asking myself in what way the relationship actively contributed to fulfilling my life goals and bring me to that ”happy place”. It has been transformative. I have since met my current boyfriend, and at the 9 months mark, I have never been as happy, supported and cared for. We are planning to buy a home together, and I have been able, thanks to the good energy and moral support this relationship is generating, to tackle a backlog of personal work I had been procrastinating on for a while. It’s this kind of concrete, take-home benefits that, on top of the romance and excitement, make me sure of wanting to move in with him in 2020.

    Olivia, you deserve someone who will make you feel like you are able to accomplish all your dreams. Your time is at least as precious as your money, so make sure you protect both. 🙂 I hope you have a lovely day, and I’m sending you lots of love. Bravo for the courage of writing everything out.

  173. Sarah says:

    Hi Olivia,
    I’m a medical student in my third year. I actually applied for the NHSC scholarship twice (didn’t get it though, it’s competitive!) so I’m really familiar with all the fine print. And one thing that no one has mentioned is that if you do not fulfill the terms of your contract with the NHSC (ie, finishing residency and your following years of service), you owe THREE TIMES the debt PLUS interest, starting immediately. They will garnish your wages, take any assets you have, and in some states being in breach of contract with the NHSC precludes you from being able to practice medicine at all. Being a physician who can’t finish residency is a financial nightmare, but if you’ve signed a contract with the NHSC, it’s 1000x worse. I recommend you go to the NHSC site and read their PDF providing information to applicants. I’m not sure I can comment on your relationship — whether to stay or go is a decision only you can make — but what I can say is do NOT legally yoke your finances together. Best of luck in figuring this all out — it sounds like you have a lot on your plate, and you’re handling it really well.

    • Dani says:

      Wow, thanks for sharing this sobering info. I hope Olivia is still reading the comments because she needs to read this to know how his medical debt and NHSC responsibilities can be exponentially greater than she realizes.

  174. KP says:

    Dear Olivia,

    I feel you on how hard all of these relationship questions are concerning a partner with ADHD. I’m writing to give perspective from someone who has dated two men with ADHD, and is now married to one of them.

    Like you, I had a lot of concerns about the behaviors and job/financial status of my boyfriend (now husband) before marriage. My best friend also had serious concerns, which made me question things even more. However, after being married 6 years now and just having our first child together, I can say I’ve never been happier!

    What I learned in the process is that you really have to trust your own intuition about the person. If you don’t have ADHD yourself, it can be very difficult and take a long time to understand how their brains work since it’s so different from your own. I would encourage you to read books for partners of ADHD. That helped me a lot and to understand that they need adrenaline to function, so often engage in “risky” behaviors. However, this can also be a positive thing. In my husband’s case, it allows him to be an outstanding performer (his career choice), but also function very well in high stress situations. I am the exact opposite and suffer from anxiety and so actually rely on him heavily in stressful situations…so we actually balance each other out! So I totally understand why what you wrote about Jacob sounds negative to most people, it would probably sound similar if I wrote about any concerns I have with my husband. But those are the areas you’re concerned about and you’re asking for advice…so naturally that’s what you focused on. It just sounds so alarming because it’s so different than “typical” for most people.

    The one key point I found to help me decide that my husband was (and still is) “the one” is communication. With my ex who also had ADHD, he was unwilling to talk about problems or discuss changes we needed to make to have a better relationship. With my husband, we talk through everything including super difficult topics. His response is always to listen, be supportive and help figure out if something can/should change (including on his side). So, having these difficult conversations others have suggested you have with Jacob may very well give you the chance to see if he is husband material. Whichever way it goes, you will then feel confident in your decision.

    I wouldn’t be as worried about any of the other things you mentioned (his debts, lack of household chores equality, etc) in their present state, because if your communication is good, then you’ll be able to work through all of it together. He may also need you to be patient and help him figure out what things to hyperfocus on (ADHD brains tend to do this) and what things not…but without telling him what to do. Likewise, he can probably help support you in ways you may not realize yet and also keep life interesting!

    Also, just brainstorming here…since ADHD brains usually function well under adrenaline/high stress and he is interested in medicine, maybe he’d do well in an ER environment? He may also need help to follow through with the more mundane/boring parts of his job. That doesn’t mean you do it for him, but maybe help him discuss/brainstorm or find a professional who can help him come up with practical ways to manage those things. For us, my husband handles tasks that I find stressful and I do the “boring” household things like finances, haha! I know readers of this blog don’t think finances are boring. 🙂

    I wish you the best of luck in navigating this period and encourage you to keep an open mind while also keeping true to yourself and your personal and relationship needs. This means if you decide to stay with Jacob, constantly assessing how you feel and continuing to have those hard conversations. Without doing this myself, I would never have discovered that one perfect role for my husband is being an absolutely amazing father to our child, always having lots of energy for her and giving us a fresh perspective every day. We’re now even considering him being a stay at home dad for the next few years while I work from home. It’s not a place either of us ever thought we’d be in, but we’re so happy!! 🙂 And as a side note since you expressed interest in having kids, I’ve found the ADHD brain handles the adrenaline/stress filled time of labor & delivery really well, my husband was so calm and my rock through the whole thing.

    Wishing you lots of happiness in your future and I applaud you for being so brave to open up for this discussion here!

  175. mandi says:

    Hi Olivia (and Frugalwoods family!),

    I discussed your case study with my husband last night. We talked about how at different times in our relationship, we have each been both the “Jacob” and the “Olivia” of our life together. Things (people, situations) seem so different looking back now than when we were in the thick of it.

    There is no right answer here. Each choice offers infinite paths that are both open and shut with each subsequent choice.
    I agree with everyone who has suggested you find a good therapist to work with, preferably long term. Not specifically to sort out the Jacob question, though that will likely come along in due time…

    Working with a therapist has been one of the best decisions I’ve ever made. My life was fine; my marriage was/is good. I am happy overall. But I had some questions come up in my life and I couldn’t figure out how to determine what the right answers/steps/choices would be. Friends and family were too close to be unbiased. I am not “fixed” and I don’t have all the answers, but I understand myself better and I am developing better skills to evaluate, decide, and cope. This takes time, but it continues to be worth it.

    Whoever Jacob is now is who he is. He may or may not be realizing his best self at this moment in time, but the same goes for you. He may be working through a rough patch in his life, or this may be a culmination of what you can expect from him.
    The same goes for you. We readers are sympathetic to you because you frankly described Jacob in a way that makes him sound like someone who doesn’t deserve your awesome self. Some of what you described seem to be facts about him that are inarguably bad (the residency thing is BAD–do not fool yourself about this). But some of it is based on how you perceive and respond to him and his actions, and how you reported that to us. So for the most part, we are finding ourselves on Team Olivia.

    Is this accurate, or are you a martyr who never plainly states what she really wants and then silently simmers when people don’t read her mind? The person who always works too much for too little pay….but who asked you to do that? The person who never says no, but is breaking under the growing load? The awesome girlfriend who wants to save her misunderstood boyfriend?

    Olivia, I don’t know if any of that is you or him, but a good therapist can help you work through all of your questions, as well as questions you may not know you have. This applies as much to Jacob as it does your questions, hopes, and fears about becoming a parent and seeking a PhD.

    I don’t know what you should do about Jacob, or anything else frankly. Relationships, having kids, seeking a degree…at some point it’s all a crapshoot. But I have been married for more than 15 years and to the topic of relationships I will offer to that is that is love is not enough. “All you need is love” is some truly crap-tastic advice. A person can have truly wonderful qualities that enrich your life, but those good qualities may not offset the problems they bring to the table and the havoc they wreak in your life. People do change, but you do not get to decide for them if, when, or how. You can love someone, but that does not mean you will have a good life together. Lots of divorced people still love each other. They still feel the spark for the person who ruined their finances and can’t be a reliable co-parent. You should not settle for someone you don’t love with all your heart, but loving someone with all your heart is not enough.

    I wish you the very best, and I hope you understand that every word I have written comes from a place of compassion for you and for all of the rest of us who are doing our best to muddle through life.

  176. Sarah says:

    1. Move your savings to a high-yield account (e.g. Ally or CapitalOne360); another 1% APY will be a quick and easy extra $20/month

    2. Definitely restart your yoga

    3. You mentioned to another commenter: “I’m so sorry that you are in marriage counseling.” On the contrary: counseling is great, and you should look into it!

    4. I strongly encourage you to make some changes at work. This line jumped out at me: “I’m the only person in my department with the skill set to answer” certain questions. This is (a) a surefire route to burnout, and (b) puts your company in a precarious situation with you as a single point of failure. Think about it this way: if you get sick, leave, change roles, etc. then they would be left in a major lurch without you. Consider:
    *Putting together an FAQ doc to circulate for commonly asked / answered questions
    *Conducting trainings with cross-functional groups with whom you interact most often
    *Adopting a strict stance on meetings: can they be shorter? Can it be accomplished in an email? Take back some Individual Contributor time on your calendar
    *Setting harder limits around your time. Decline meetings that coworkers schedule during your lunch hour. Add “heads down” blocks and turn off notifications during that time
    *Streamlining and automating your processes wherever possible

    5. Based off your description of your house, I believe Allie @ Wardrobe Oxygen is located nearby: Check out her blog, she is always doing something around the neighborhood and has great DC / Greenbelt recommendations!

  177. JB says:

    Hi Olivia!
    You have plenty to read here. I hope you’re still scrolling through, even though it must be so hard. Look where you are ; your plans and future are stellar and I think you’ve made a huge impact on many people by stepping up and writing this case study.

    Financial/Life Goal Stuff:

    – Did I miss the “why” in regards to the PhD? I really understood how much enjoyment you would get from it, and, it certainly makes sense financially on the front end in that it will be free or near-free for you to obtain. But I noticed so many possible areas of study that you listed and wondered how you see it applying to your future? I would try to sit down and picture how you see having the PhD potentially impacting your career and go from there. Remember: “Start with the end in mind.” Will it help you in your current position or, is it a move to create a bridge to something new down the road? Come up with your why and help that guide you to your field of study.

    – You wrote that you love learning and love research. You sound a little like me in that respect. So, if it were me, I’d take it as slow as possible and really savor it. After all, it’s for the fun of it, right? Not because you’re desperately hurtling towards a promotion or new job. So take it easy and really enjoy it while you continue to work and kill your financial goals at the same time. Time-wise this is even better if Jacob moves away, you’ll have that space to really soak up all that you’re learning. You’ll meet a lot of like-minded hard working people in your program and through them you will make connections and might even catch a glimpse of where you see this degree taking you long term. It could be so much fun!

    – The next few years can be spent building your life so that there is a nice big welcome spot for a child to be, Jacob or no Jacob. If you need to take time away from your program (and you might!) you aren’t accruing debt from it, and you don’t *need* it, so you can pause and eagerly await going back at any point, or just taking school even slower as you focus on your kiddos.

    – Your vision of your life seems very laid back and as simple as can be. Sounds like you would be happy with very little. You gave us your ideal day as, “I’d really enjoy being able to get up every morning, do yoga, have a cup of coffee, tend the garden, actually finish a New Yorker, and enjoy some silence.” That life, I imagine, IS SO MUCH CLOSER than you think and requires very little. With/without PhD. With/without Jacob. With/without kids, even! You are a mere decision away from making your ideal day a reality a little at a time each day. Wow.

    A lot of people have learned from you through this public case study, reading and thinking, “wow, look what she’s accomplished!”. It’s also been eye-opening for me to read through just how many (women, mostly) who have their own stories to tell about heart breaking hardships in relationships, trying to share for you what they’ve learned, wishing they’d had similar support and advice. These comments will be here indefinitely for you to look back on, when you’re ready to look back on them, IF you’re ready to look back on them. You may not need to. You already, instinctively know quite a bit about how your future looks.

    When you were single, you were not actually single. You were in a relationship then with YOURSELF and you were an AMAZING partner, Olivia. You had the resources to provide you self care, creating a secure and damn-near idyllic future. You made space and had a plan for babies, you surrounded yourself with family, you found a home in a place that makes you sparkle, and even gifted yourself a whole room dedicated to your wellness. You were a stable provider for yourself, and found a position in which you are valuable and talented. You didn’t overspend, you didn’t load you down with debt – you in fact built a bright road to the future with a solid net worth! You allowed yourself to dream and plan and be educated and reach for even more!! You didn’t hold yourself back when you were your partner. That whole time you quietly taught yourself that you already possess the qualities of the ideal partner. You don’t need anyone from the outside, because you already have the ideal person tucked right inside of you. Jacob or any man should be the icing on the cake. Looking at any partner you instinctively know whether they rise up to the kind of partner you have been for You.

    It is all very close. I can see this all working for you and being a really, really fulfilling life.

  178. A human like you says:

    Hi Olivia,

    Nothing like putting your heart out there for all to comment on, you brave woman! Here’s some questions from a woman who married the most sparkly, open hearted, creative man with ADHD when she was in her 30’s and still married, almost 20 years later:
    Does her make your heart all glittery goodness and being without him, inconceivable?
    Would you continue to feel that way if he didn’t finish his residence?
    Would you continue to feel that way if he lost jobs throughout your years together?
    Did he take responsibility for his problems with the residency and worked to fix them or is he blaming the situation/ lack of accommodations?
    Is he the type to blame others or make excuses for problems that arise?
    Is he looking to addresss his ADHD?
    Are you comfortable acting in the role you are in for the rest of your relationship, and when you add children to your lives?
    Are you willing to take on the financial property management of the family home in addition to your other daily tasks, because you have the “skills to do so”?
    Are you willing to move or spend most of your time off traveling to the family property vs elsewhere?
    Do you enjoy his family enough to spend extensive time together at the family property?
    Is Jacob truly suited and passionate about becoming a doctor, or it someone else’s expections?
    What if you became a doctor and he didn’t achieve his goal, would you try to dim your sparkle or not pursue your goals out of concern that Jacob might feel inadequate?
    What in you life experience made you believe that you needed to be overly responsible at work and in a relationship at sacrifice of your own wellbeing (hint it’s likley from your childhood and it’s related to your parent’s roles)?
    Are you comfortable with learning how to set boundaries with those you love so you can get your needs met, as well?
    Often auto immune diseases occur with chronic stress and lack of self-care, if you were to get sick, how would Jacob take care of you?
    ADHD is often heridetary, if you had children with Jacob and they also had ADHD, how would that impact your life?

    None of us well intended readers know your experiences, and what is right for you. Ask yourself and Jacob the hard questions or work with someone who can help with these important discussions.

    As someone who has asked the questions, and still asks almost 20 years later, be well dear friend!

  179. Jen says:

    Wow. You’re getting more relationship advice than financial. I’ve been in a similar situation to yours–both financially and relationship-wise–and I’ll say that 1) it’s possible to deal with the finances. Anyone who doesn’t understand med school isn’t going to understand that amount of debt and income potential. The fact that he can apply to be a doctor now means he has the ability to pay off that debt. 2) Your relationship is your own; you understand it better than all of the people commenting based on only the financial aspects of what you have listed. 3) You have to determine if you want the relationship because you want the person or because you simply want a relationship. With any relationship couples should discuss finances, household responsibility, etc., so that’s not limited to your situation.
    I also want to add to your comments about your line of work. Unless you plan to teach, a PhD isn’t going to do much for you income-wise. You’d be better off with furthering professional development in stats and pursuing work in that area. A PhD is also *very* stressful, and it sounds like, at least at this time, stress isn’t something you want more of. If you are looking to raise income, you can look into something outside of academia or, if wanting to stay in academia longer, you may want to look into actuarial science and whether you can pursue further training in that area for a career that is very lite on stress and high on income.
    Good luck as you navigate your career, finances, and relationship.

    • Emmy says:

      “The fact that he can apply to be a doctor now means he has the ability to pay off that debt” – unfortunately, it doesn’t. Being fired from residency is going to haunt him, permanently. At this point, ever being a doctor is pretty much a pipe dream, people who have better track records will be considered ahead of him for EVERY opportunity; few will even consider the risk of bringing him on. At this point his best bet is to get a job based on his masters and start paying down that debt. Good news is maybe he can do that from Vermont, helping with the family LLC on the side; at least he might be able to have a place to land where he’s not charged rent so he can really put some effort into paying it off before he’s 60.
      I’m not a doctor but there are 2 in my family who both work and teach at a major medical university on the east coast. That he got as far as he did and then was dropped from a residency…. maybe he burned out? It’s late in the game for a burnout, usually if it’s going to happen it’s earlier than residency.

  180. Gina says:

    Hi Olivia,I read nearly all of these comments pre-Christmas – what an array of stories and thoughts! I’ve never commented before, but I’ve been thinking about you and all of these comments and I want to share a quick additional one, for you to take or leave. When I met my husband (at age 28) he had just enough money in his bank account to buy me a coffee. Literally. While his undergrad debt wasn’t terrible compared to 300K, he was making very little money and so it was impossible to pay rent while also paying his monthly payment on his debt. He was living with his parents and driving a Toyota Corolla with a billion miles on it.
    The night I met him, I knew I was going to marry him, so our life conversations happened pretty quickly. What I found was that he was ashamed and embarrassed and didn’t know what to do. He feared he wasn’t smart enough or qualified enough to get a different job. He also didn’t have a good grasp of how to think strategically about money – how his interest was working, what his options were, and how much money he would need to make to get squared away. I helped him a lot with that. 
    hat’s what a partnership is – each of you brings strengths and struggles. I wanted to help because I loved him and he wanted to be brave and face it because he loved me. Sometimes you need your partner to help you face something that is scary or that makes you feel embarrassed. I mean this very respectfully – it must be mortifying to be fired from residency. It’s extremely uncommon, everyone knows, and it can have huge impacts on his career. That’s a lot to deal with. If you love him, and you want to be in a partnership with him, I would frame it as your collective goal to figure out next steps and see whether he is on the same page with that team approach. It’s not that I think you have to take on his debt as your own, but I think when you view yourself in a partnership, goal setting and planning and maneuvering has to be collective because it impacts both of you. If he isn’t showing you that he wants to take steps to get on track, and if he isn’t more worried about the way his choices/actions/life circumstances are impacting you than he is about himself and what he wants, in my mind, that’s your answer. But if he is, and it’s just that he needs your help to get onto a good path, I think this can serve as a foundation of your relationship. I wish you both the very best!  

  181. Lisa says:

    Run, I’d never marry someone with that much debt or that many problems. I was very selective when dating, and carefully choose a husband with little debt, a good work ethic, and no baggage. Thirteen years later we are still happily married and I mentally thank my now deceased Grandma for drilling this boring practical stuff in my head when I was young and starry eyed. Especially if you want to have kids, you don’t need to take on all of these problems.

  182. Lisa says:

    Liz, how does one submit a case study? Love this blog, been reading it for years, today is my first time commenting.

    • Mrs. Frugalwoods says:

      Hi Lisa! Thank you for reading and commenting! For anyone interested in applying for a case study, send me an email ( with your brief (a few sentences) story on why you’d like to be a case study. If you’re selected, I’ll send you worksheets to fill out for the complete case study. Thanks!

  183. Sandra says:

    When can we expect an update on Olivia and Jacob’s financial decisions/progress?

  184. Buckeyecub says:

    Haven’t finished all the comments yet. Wanted to mention that you should check that your lender will remove PMI for your coop. We have a condo and when we got below 80% asked the lender to remove PMI. They refused and said that condos didn’t get PMI removed. I never hear anyone discuss this but we tried more than once. Just don’t want you to prioritize something that might not be option.

  185. Emmy says:

    Just found this case today, very impressed with what you’ve managed to accomplish on your own in education, finances, and housing. That said…

    My first husband had difficulty with responsibility. It was a lot like having a child (albeit one who carried a credit card, drank to excess, and made really bad choices). I decided I couldn’t live with the stress and financial disparity (he made 3x as much as me but I was always cleaning up his excess spending issues) and divorced him. Thought I’d be alone for good – nearly relished the idea, because I couldn’t be any ‘worse’ off without him than I was with him.

    At just shy of 33 I met a nice man. Had his act together. Didn’t drink much, didn’t spend much, liked to save, liked to have sober fun. The only problem with him? He couldn’t cook. Literally couldn’t have boiled water…. Married him anyway, had a kid at 35, another at 38-3/4, taught him to cook, and now he cooks more often than I do.

    All that to say “Oh, honey – You can do SO much better.” Fiscally, you’d be so much better off not tying your wagon to his. As a parent, at least when it’s just you parenting, you know you’ll do the work – you’ll go in expecting to have to do the work.. If you go in expecting HIM to do 1/2 or 1/3 or even 1/4 of the work of parenting, I suspect you’ll be terribly disappointed.

    What do your parents and sibling(s) have to say about him?

  186. Kim says:

    How does one get featured as a case study here? I had sent a few emails to the address mentioned but never received a response. Just want to be sure it’s going to the right place…or maybe Mrs. F is just inundated with so many requests from readers that she can’t respond to them all.

    • Mrs. Frugalwoods says:

      Hi Kim! You are correct that my email inbox is a horror show! It’s a goal this month for me to clean it out and respond to everyone (wish me luck!). I’m embarrassed that I’m not more on top of replying to everyone who contacts me and I apologize.

  187. Chris Taft says:

    You have two potential directions and you don’t know which you will pick. You will eventually marry Jacob and take pn all of his issues both financial and healthwise. Or you will breakup with him and continue your basically great money and life management either singly or with someone else. I would suggest you continue financially as if Jacob will not be in your life while working with him on what you want to happen and how he is going to help get there. This may mean a long distance relationship for awhile but better that than give up your job and home until you have worked these issues out. You may have to budget for flights and couples counselling while you work through this but I and everyone else who read this have great confidence in your financial ma nagement abilities. Hang in there.

  188. Faith says:

    Oh Olivia — congrats on all your amazing choices and planning, but RUN, do not walk, away from this guy. I speak from experience, but this article sums it all much more eloquently than I could.

  189. Coral says:

    Olivia, I’m hoping you’ve been having a happy break over Christmas, unless I’ve missed a post, it’s been 6 weeks or so since we last heard from you. I’m hoping we haven’t discouraged you by saying things that are hard to hear. I’m sure the comments have been made with your best interests at heart, but I recognise that you may be seeing positive changes and growth that give you reason to continue investing in the relationship. We are, I know, United in wishing a happy future for you, whatever choices you make.

  190. Bob says:

    I am dying for an update to this story. I realize we’re in the midst of a pandemic, but I am especially keen on finding out if Olivia took the advice of every medical professional who commentated in regard to the BRIGHT RED ALARM BELLS!

    • CB says:

      Me too! I just read this and am really curious to see how things have panned out… if Olivia decided to make any changes, I hope she had the chance to do it before the pandemic!

  191. Sandra says:

    Really would like to know how everything turned out please.

  192. Sarah says:

    This story has really stuck with me — Olivia, if you’re out there and are comfortable sharing an update, I think a lot of people are rooting for you and wondering how things have gone for you this year.

  193. Carrie says:

    Hope all is well with Olivia! This case has stuck with many of us. Wishing her the best.

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