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 (mrs@frugalwoods.com) 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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  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!

    1. 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.

      1. 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!

        1. 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.

      2. 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.

        1. 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.

          1. 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.

    2. 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….

    3. 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?

    4. 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. 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.

    1. 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!

      1. 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.

    2. 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.

      1. 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!

      2. 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.

        1. 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!

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

    3. 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.

      1. 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.

      2. 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.

      3. 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.

      4. 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.

        1. 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!

        2. 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.

          1. 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! 🙂

    4. 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!

    5. 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.

    6. 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.

      1. 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.

    7. 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.

      1. 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.

        1. 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.

        2. 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.

        3. 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.

        4. 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.

        5. 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.”

      2. 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.

    8. 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!

    9. 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. 🙂

    10. 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. 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. 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.

    1. 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

      1. 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 😊

        1. 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.

  5. 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.

    1. 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.

      1. 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. 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.

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

      1. 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. 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.

    1. 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.

      1. 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.

    2. 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.

    3. 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.

    4. 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.

    5. 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.

      1. 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. 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.

      1. 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. 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. 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.

    1. 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?

      1. 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. 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

    1. 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. 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. 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!

    1. 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. 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.

    1. 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!

      1. 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.

        1. 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.

    2. “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?

      1. 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. 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.

    1. 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. 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.

    1. 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. 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 🙂

    1. 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. 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. 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.

    1. 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. “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. 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. 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?

    1. 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. 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. 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.

    1. 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. 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).

    1. 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.

    2. 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.

      1. 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.

    3. 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. 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. 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. 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.

    1. 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. 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. 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.

    1. 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.

      1. 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.

  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. 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”.

    1. 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. 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.

    1. 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 🙂

      1. 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. 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. 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 – https://www.madfientist.com/sane-fientist-interview/ (Also, like Mrs. FW said, definitely worth talking with a lawyer if you go that route)

    1. 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. 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. 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.

    1. 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. 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. 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.

    1. 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.

  40. 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. 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. 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. 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.

    1. 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.

      1. 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.

      2. 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! 🙂

        1. 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!

  44. 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?

    1. $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. 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.

    1. 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.

      1. 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.

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

      2. 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.

    2. 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.

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

      1. 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.

        1. 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. 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!

    1. 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.

      1. 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. 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. 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. 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. 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. 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. 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. 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. 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.

    1. What a great phrase!
      I met my partner after y e a r s of singledom. I know the eagerness to make it work. But if it doesn’t, it shouldn’t.

  55. 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. 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.

    1. 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. 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. 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. 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. 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?

    1. 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.

    2. 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. 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!

    1. 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.

    2. 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. 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. 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.

    1. 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. 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. 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. 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. 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. 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!

    1. 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!

    2. 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. 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. 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. 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!

    1. 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!

      1. 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.

        1. 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!

          1. 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. 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.

    1. 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. Olivia,

    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

    1. 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.

      1. 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 😍

      2. 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.

      3. 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. 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. 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. 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. 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. 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.

    1. 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. 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. 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. 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!

    1. 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. 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. 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.

    1. 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. 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. 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. 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?

    1. 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.

      1. 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!

        1. 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. 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.

    1. 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. 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. 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.

    1. 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. 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!!!

    1. 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!

      1. 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. “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?

    1. 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. 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. Olivia,
    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.