Hey Captain Awkward.

I read some of your responses to other writers who had concerns about their partners’ finances, and I feel like this is related but not quite the same.

I’m stressed about my boyfriend’s money management skills and how I can help him without getting myself into a bad financial situation. I also recognize that he’s probably embarrassed on top of being stressed, so I’m trying not to make him feel ashamed. He was raised below the poverty line and when he made it “big” in his industry, he was earning huge salaries, so I think he’s allowed himself to fully enjoy it. Now he’s unemployed but is still living a “huge salary” lifestyle.

About me: I’ve always lived pretty frugally. I’m kind of a prepper in some ways – I buy a lot of dried or bulk foods, and I park nearly a mile away from work and walk every day so I don’t have to buy a $400 annual parking pass, plus I get some exercise which is hard to come by in my 9-5 cubicle lifestyle. My mortgage is manageable, 90% of my furniture is thrifted (thank god eclectic/Boho decor is “in” right now), I pay my bills on time, I have a modest emergency savings, and I have excellent credit — with a little bit of revolving credit card debt. My house is my first home purchase, and in addition to receiving some assistance from my grandparents, I participated in a federally funded first-time home buyer program and saved for years to come up with the down payment. My house isn’t fancy, but I love it because it’s mine goddamnit, and after changing addresses every year for 18 years, I finally get to lay down some roots! I‘ll hit my one-year anniversary of homeownership next week. Yay.

I do not typically seek out partners with tons of money. In fact, I’ve been known to date transient wildlife biologist types who briefly stay in the area to work for six months out of the year, and then squirrel their earnings away to get by the other six months. I just happened to fall in love with my BF who – up until last summer – was successful in his career, made a lot of money as a senior level designer with some recognizable household brands, and was promptly relieved of his duties the same week we met. He felt it was a blessing in disguise because he’s burned out on doing design for a living and wants to pursue his passion of selling rare European cars.

BF was earning a gratuitous salary last year, and while he lived within his means, said means were extravagant and now unsustainable: he owns two houses and has 7 cars (or 8? I actually don’t know anymore). Again, cars are his hobby/passion, as well as his side business, so some of this is to be expected. Two of them are “investment” items that will continue to appreciate in value, two are for driving, and the rest are “projects” that he plans to sell… but as you might imagine, this ties up a lot of capital in non-liquid assets.

BF is hemorrhaging money, but not cash, and is putting a lot of charges onto credit cards. He justifies this by saying that most entrepreneurs fund their businesses through credit. BF also owes his best friend a sizable amount for a recent generous loan which seems to have strained their friendship a little.

Three months ago, BF put his second house, which is in a popular resort town a few hours away from where we both live, on the market. He’s received multiple offers on the second house, but due to complications beyond his control, they continue to fall through, and so it remains on the market. BF was relying on the sale of this second house to kick-start the car business.

His monthly expenses (e.g. mortgages, private school tuition for his two kids, and commercial space for his new business) are over $5k. Not included are utilities, groceries, gasoline, health insurance, pet expenses, or anything else fun/recreational like an occasional meal out or outing to the nearby large city. BF has very little income right now except for infrequent freelance design work which he loathes and the car side hustle. Currently, he sells a car every 4-8 weeks and each sale results in a few thousand dollars. I in believe he’s receiving unemployment, but I’m not sure that he’ll qualify for much longer.

I told him he could sell his primary house and move into mine if he wanted. My mortgage is literally half the size of his, and if he paid HALF of my mortgage he’d still save $2k/month. However, he doesn’t want to sell his primary residence for a lot of (legitimate) reasons, and he wants to keep trying to sell the vacation home that’s been on the market for four months. OK, I get that… But right now, it’s just him and his dog occupying a 3,000 square foot space. He wants me to rent out rooms in my house and move in with him (I would contribute to his mortgage, which would only cover 25% of his monthly payment). I am considering it, but I’m also so happy to finally have a home of my own… it would make me sad to move out of my first home so soon.

I know he’s filed for bankruptcy once before, and he recently said he doesn’t want to do that again (he said it semi-jokingly, so I don’t know how much of a real possibility it is for him). He also told me early on that he thought I’d be a good influence on him as far as spending habits go. These were yellow-orange flags for me at the time. Now, he’s asking me to go with him to a cousin’s wedding on the absolute opposite side of the country in two months. We both have airline miles that will cover the trip, but it’s honestly not how I want to use those miles — the whole reason I got a credit card that gives airline miles is because he suggested I get one so we can travel overseas together this year. I wouldn’t have taken out a second line of credit if I didn’t think we weren’t going to use it for an *international* vacation. Plus, the wedding trip in two months becomes more expensive when you add up the other items that will not be covered: lodging, dining out for five days, hiring a pet sitter for our two dogs, rental car, etc. And I’m also just feeling less and less secure about out future together as the weeks roll by. Like what kind of message would I send to his family by attending this big family event if I’m not sure how into/secure I feel about the relationship by the time the wedding rolls around?

He has also half-joked about how I should have offered to pay for a recent ticket he got because he’s so broke. (He wouldn’t have received the ticket in the first place had he agreed for us to take my car that morning — which gets twice the MPGs — instead of his… but he insisted on taking his car. It apparently didn’t have a front license plate which resulted in a ticket.) The irony is that I almost offered to pay for it as a “sorry you’re broke, happy belated birthday” gift… but after he said that, I thought “NOPE. Nevermind; I don’t owe you shit.”

Let me preface that BF is the closest I’ve found to “my person”, if you get me — our connection, chemistry, and compatibility are mind bending. I’ve dated a lot of people in my day and never felt about them the way I do about him. I want to live with him at some point, get married, and maybe even have a child. How can I communicate my concerns to him without compounding his stress and sounding like a tightwad? (Also… Am I a tightwad? I’m starting to doubt myself and my saving habits…) And how do I support him without getting myself into a bad financial situation of my own? I don’t want to lose my savings, wreck my good credit, or be his cash cow, but I do want to be there for him in a way that empowers, not enables. I can see a future with him… so do I just sit tight through this rough spot and hope it all works out soon, or am I aboard a sinking ship and just don’t have the perspective to see it? Also, is there a way I can get out of attending this wedding?!

Thanks Captain Awkward!

Hello! I am so glad you wrote!

And congratulations on this month’s award for “burying the lede”! I retained the subject line of your email as the subject line of the post because I wanted readers to ride the same “oh, only 7 cars? Or is it 8?” roller coaster I did. 🙂

You have been so candid and such a good advocate for yourself that it makes my job very easy. My advice is:

Do not jeopardize anything about your finances or housing to “help” or “support” a man with 2 houses and 7-8 cars.

Re-examine the idea that it is your job to help him figure out his money & his relationship with money.

I’ll elaborate but here are some scripts:

“I do not want to move out of my house.”

“I do not want to move out of my house to make housing payments on a house I don’t own.”

“I’d rather save my miles and money for a vacation than go to that wedding, and I can’t afford to do both, so you’ll have to fly solo on that one. I’ll have to meet your family some other time.”

“We approach money really differently, and I do not think it will be good for either my credit score or our relationship if we combine money or housing, especially while you’re still getting your business off the ground.”

“I want to help you through this, but ultimately it’s your money and your decision, so one way I can ‘help’ is by having really clear boundaries especially around financial decisions that affect me.”

Additionally, scriptwise, be very blunt and specific about money in your dating life. Do not let this flounder in expectations and hints, get in the habit of nailing stuff down like where are we going, what is the anticipated cost, who is paying. When you are offering to pay, make that offer up front: “Can I take you to ____ tonight? Dinner’s on me.” (This is a good thing to do anytime you are treating a known poor-er person, the anxiety of guessing and mentally running the budget numbers is just awful and fun-destroying). When you are splitting costs or expenses, settle up right away. “The bill is ______, do you want the waiter to split it for us or do you want to pay and I can Venmo (etc.) you my half?”

This may seem unromantic and tedious, and it might bring out some weird shame behaviors and avoidance in him, but do it anyway. If you can’t afford something, say so. “That sounds nice but pricier than I can handle right now, can we save it as a treat for next month and stay in tonight?” Make this shit matter-of-fact and normal. Make yourselves a couple who can talk frankly about money in mundane, routine ways that doesn’t require big negotiations or emotional processing.

It’s hard to write about how people handle money without writing about how we see “virtue” and morality and value. Your boyfriend’s prior success and big lifestyle has aspirational qualities, he has what everybody is supposed to want, right? Having achieved it means that certain doors open for him that were closed before, he will be more likely to be listened to, to receive the benefit of the doubt, to receive additional credit, to be seen as “a solid guy” even if everything underneath is paper.

Your thrift is also seen as Good, people will also give you credit (literally and figuratively) for having a solid credit rating and learning how to navigate government programs and paperwork to invest in your house and keep your finances in order. I’m writing this in the United States, where people are supposed to act like you in order to become like him, if that makes sense, and where the collision of “wealth,” “thrift,” and “deserving” are part of our origin story.

The Protestant* Work Ethic: “See this book, about a poor guy who flipped tables and yelled at rich people to stop being assholes and told them they’d never get into heaven if they didn’t change? It’s the best book right? “ European Colonists: “Yeah!” The Protestant Work Ethic: “What if it’s really book about how struggle is good for poor people, but being rich is awesome and a sign that you are morally better than poor people because God is clearly rewarding you for how good you are?” European Colonists: “We’re listening” White Supremacy: “Also, white people are the best people because of how hardworking we are.” European Colonists: “Thanks for noticing! But you meant white people and of our specific church, right?” Protestant Work Ethic & White Supremacy, in unison: “Of course! So white people deserve all the land and wealth, and rich white people deserve the biggest share of those things.” European Colonists: “Sold!” Protestant Work Ethic & White Supremacy: “So we agree that people without wealth, land, or resources deserve to be poor, and if they want to not be poor, they have to prove they deserve it, right? Otherwise it wouldn’t be fair!” European Colonists: “Oh yes! We want to be fair!” Fast forward three hundred years of colonialist capitalist hegemony… The Prosperity Gospel: “Hold my beer…” *Catholic churches and other sects certainly made friends with the wealthy and powerful, but the Pilgrims, etc. had that specific worldview so that one had more time to spread and germinate specifically here.

It doesn’t matter what you personally believe, this is the shitty culture, this is the shitty history, this is the shitty capitalist air we breathe (which can legally be a certain amount of polluted if it makes certain people enough money) and the shitty capitalist water we drink (which can legally be a certain amount of polluted if the polluters can show they created a certain number of jobs) and it takes some effort and pushing back to say, I do not think we are what we earn, I do not think that certain things like “shelter” and “health care” need to be “deserved,” I do not attach shame to things like getting into financial trouble or needing help or being unemployed, and I do not think a good credit rating or money in the bank has a moral value, or that men have to be “providers” in order to be good people or partners. But those attitudes still affect me and everyone around me.

You, the Letter Writer, don’t buy into patriarchal ideas about who should Earn The Money in a relationship, you are trying hard not to judge your boyfriend for falling on some hard times and handling it badly. I am trying to do the same and yet, we are made of contradictions because when I read your letter a deep, unusually resonant voice came out of me and that voice said,“Nononononono, you do not fuck up YOUR. MONEY. for a man who can’t manage his.” You didn’t specify pronouns but from what I can observe I’m pretty comfortable tagging this post with “Feminism.” Too many of the stories of a good, no-nonsense woman who bet on a man with a dream end with the guy rich and the woman much worse off and I am kind of done with those in both fiction and life.

Look, I think it matters a lot that your boyfriend has a different car for every day of the week (and two for Sunday Best!) and that you do not live that way. You are talking about financially “helping” someone who is, by any standard, wealthy. Wealthier than you, by a lot. What? How? No.

And look, also, I think it matters a lot that he isn’t paying his best friend’s loan back in a timely fashion. I don’t think having debt is bad, but he is showing you that he will test and risk an important relationship rather than make tough money decisions. That’s a problem.

It matters because this guy will not be destitute if you do not help him. He will have to make some hard decisions that he has been putting off and would like to keep putting off. He does not want to be a person who doesn’t have a vacation home anymore or who only has one car for driving his one ass around town. He wants you to move out of your house that you love and give it over to tenants, or spot him money for this family wedding, so that he can keep appearing prosperous and thinking about himself as prosperous. With your help, maybe he won’t have to reckon with a bunch of shitty, boring, annoying decisions and shitty, boring, annoying, paperwork and the reality that changing careers to try to make a hobby/passion pay out means sometimes saying “No, I can’t afford that.”

You mention that your boyfriend grew up poor and I can believe that. I can believe that once he “made it” he spent money like someone who has no idea how to be with or manage money – which who would have taught him, who would have believed this knowledge would have been necessary someday? I don’t judge it, I honestly don’t, I think that when you suddenly have a lot after a long period of having nothing, on some level you don’t believe that it’s here to stay, so why not enjoy it while it lasts? And why not live like the people you see around you, especially when you realize that rich people aren’t smarter or better than anyone else, they don’t have some secret (or, if they do, the secret is “more money”). He’s not alone, there’s something very primal and human about this, like, there’s a reason that the Rodeo Drive shopping scenes in Pretty Woman land so satisfyingly even to this day. Your boyfriend went from struggling to being a person who could buy anything he wants, and over time that became an important part of how he sees himself, his identity. He’d do a lot to avoid losing that identity, so he’s holding onto the trappings as hard as he can. And who wouldn’t want to hold onto that, if they could? That’s the story he’s telling himself and you right now – “I fought so hard for what I have, you’re not going to stand by and let me lose it, right? You believe in me, right?” He lost his job (which happens), all the offers to buy the vacation house “fell through” (which happens) but there’s a recurring whiff of nothing ever being precisely his responsibility here (the traffic ticket comes to mind) that I am not loving.

By contrast, you call yourself “a tightwad.” Since I assume you don’t go out to eat and then leave your servers a pamphlet with elaborate justifications for not tipping instead of money (the bad kind of cheapskate/tightwad, who uses the virtuous ideal of “saving money” in order to bully and control others), I have to ask, is that such a bad thing to be? (And who, exactly, is using that word, because if this guy called you that I can stop being polite about him, right the fuck now, and dismiss that for the obvious manipulative “negging” bullshit it is, though if you are using it as an insult about yourself I also have questions? If “I do not want to give up my house so you can keep all 7 (or is it 8?) of your cars” makes one “a tightwad,” then, where can I join Team Tightwad and is there a uniform and is it “whatever you already own that looks nice”? COUNT ME IN.

To me you sound like someone for whom thrift was a necessity for a very long time so you found a way to take pleasure in your daily walks back and forth to work and your pantry full of beans and your emergency fund. You wouldn’t expect anyone else do take exactly the road you took, but you’ve made it work for you after a very long struggle, and I’m so glad to imagine you waking up every day for a year in a house that’s all yours. You know who you are, you know what you need, you know where you live, and I do not want to see you put any of that at risk for someone who is so incompatible with you around money.

You can love someone and have great chemistry with them and there can still be serious incompatibilities that mean a life together will be a life spent playing certain levels on Hard Mode. You and this boyfriend being together means that money – a thing you, personally have worked extremely hard to understand and tame and make manageable for you – will become fungible, uncertain, and messy for the near future and maybe forever. And that is a very big deal.

This is one of those moments where I’d give a lot sit his ex (his kids’ mom, specifically) down and ply her with drinks and ask her questions about money and what kind of fights did they have about it when times were good and what kind of fights do they have about it now that times are bad and everything is going on the credit card. I don’t suggest you actually do that – my advice is for you to become less involved, not more in his money issues – just, I’d be very curious to know and I’d be very curious to know how it matches up with what he says they fought about around money, and how it matches up to the fights that you and he are inching toward now, the one where “I don’t want to move out of my paid-for house into an un-paid for one where I’m not on the deed” (a completely reasonable position) turns into “Why don’t you believe in me?” (an emotional thing that is impossible to measure). “I don’t want to spend this much money on that wedding, sorry, I’m out” = “Don’t you want to meet my family?”

I don’t know why I feel this so strongly, but I do: To accept responsibility for “helping” this guy’s financial well-being means, on a certain level, risking becoming a target for his manipulation and blame for when things don’t work out in his life. And it creates a dynamic where, you’re invested now (literally) so “you might as well” help with the next thing, and the next.

This is a problem on many levels, because he’s not living in his financial reality as a guy who lost his job and has to make some big changes, instead he’s trying to postpone a loss of identity as A Rich Person. Which, I can empathize, but I can’t care all that much whether a formerly rich guy still gets to “feel” rich, and I definitely can’t invest in that at your expense. You care about him, you don’t care a fig about whether he is A Rich Person, you want to live with him snug in your adorable house and save up together for interesting vacations. This is a great thing to want, and a thing that would be very doable probably if he would just deal with his shit. You can’t deal with it for him, he has to do it himself, he has to do paperwork and phone calls and spreadsheets and say goodbye to some fancy cars and maybe call a bankruptcy lawyer to “explore his options” and he has to do some “boring” freelance design commissions because sometimes that’s what you have to do when you’re someone’s dad and when you borrowed money from a friend. He probably needs to download one of those boring money management apps and enter every boring cent he spends into it so he knows how much money he actually has, and next time he gets rich he still has to keep doing that. Probably he needs to get a therapist and talk about his shame and money issues. You could helpfully say “Here is the boring budget tracker I use” or “Here are some sliding-scale therapists that take your insurance” but you can’t make him do anything about it. He has choices about acquiring financial literacy and emotional stability and more resources than many people do for acquiring them.

Meanwhile, as long as he’s in this weird identity crisis where he’s not dealing with his money problems head on, you’re going to have more awkward “jokes” and “hints” about how you should pay his speeding tickets/25% of his mortgage/his half of the travel expenses/the fancy trip he promised his kids/the fancy lunch for a potential fancy car customer/1,000 little things he “needs” to keep up appearances that he is doing just fine. The more enmeshed you get financially, the weirder (and possibly a lot meaner) the jokes will get because they will be a way of processing his shame and fantasies about who he is in a way that isn’t direct and doesn’t make him have to change anything. You are a person who is (reasonably) like “Yes, follow your passion, but you want to spend how much on what exactly, and when will this be resolved?” If he can’t deal with his shame and with his money incompetence, even with the best intentions over time the two of you are gonna grate each other to dust. This is what I mean by incompatibility and playing life on Hard Mode, because if money is a thing the two of you can never really relax about together, is that a sustainable thing for a possible marriage and/or a co-parenting situation?

Does this mean break up? I don’t know. It’s completely up to you. I strongly recommend not combining households or bank accounts until he’s made some giant changes. I strongly recommend maintaining some fierce boundaries around how you spend money, which is a thing you can control. I think continuing to build your own fuck-off fund is a better use of your money than getting his business off the ground. I think paying attention to the way he speaks to you about money and the actions he takes about money (like paying back his friend) will show you if this is a temporary problem of adjusting habits and expectations or a fundamental incompatibility.

So, where does this leave us? Remember that feeling of “NOPE. Nevermind; I don’t owe you shit.” you felt about the traffic ticket? I think that was a very good instinct, and I think any time you start to doubt yourself (“Wait, is the problem that I’m TOO GOOD with money?”) or feel tempted to just go along with what he wants even when you sense it’s not in your best interest, I’ve got scripts that are between you and you to remind you what’s true:

“He’s not paying his best friend back for a loan, so why would I ever trust any promises about paying me back?”

back for a loan, so why would I ever trust any promises about paying me back?” “I’m not going to give him any money that I can’t easily and happily part with as a gift.”

“I love my house and I don’t want to move.”

“I’m not living anywhere my name isn’t on the deed or that doesn’t make good financial sense to me.”

“If he moves in with me, what kind of written agreements do we need to make that work (esp. if I need him to move out) “? Let’s plan it all now and put it in writing.

“? Let’s plan it all now and put it in writing. “I’m not moving from an affordable house into an unaffordable one.”

“I really want my boyfriend to sort out his finances, he’s an adult and he can make his own choices about that.”

“I can love someone without taking on all their problems or trying to fix them.”

“I don’t owe him shit.”

him shit.” “I have good boundaries about money and good money management skills, anyone who tells me this is a problem is possibly not acting in my best interest.”

“Boundaries aren’t mean, if he can’t set good boundaries about money that means I need to be even more careful about it, not less.”

“Hold up, he has seven cars. How is this my problem.”

I’m sending you so much love and admiration, you are such a strong advocate for yourself in your letter, I think you already know everything you need to know about what to do next to take care of yourself and make sure you thrive. I hope your boyfriend makes some good choices that show you that he’s willing to work on himself, please know that I’m wishing you every good thing.

P.S. If you watch Uncut Gems and anything in the movie reminds you of your boyfriend, SKIP DIRECTLY TO BREAK UP.