Personal-finance columnist Charlotte Cowles asks the nosy, revealing, sometimes uncomfortable questions about money so you don’t have to.
Photo-Illustration: by The Cut; Photos: Getty Images
Breakups are complicated. When money’s involved, they’re even messier. If one person owes the other a debt — or the other claims they do — there isn’t much in the way of protocol: Unlike divorces, regular breakups involving unmarried couples aren’t governed by family law, so exes have fewer apparent ways to settle arguments over who paid for what. Civil court can be an option, but informal IOUs don’t always hold up — and the associated legal fees may not be worth the battle. (Of course, as any fan of Judge Mathis knows, financial disputes between former romantic partners are quite common in small-claims courts.)
Below, four women share their own experiences of owing (or being owed) money after a breakup, how they handled the debt, and what they wish they’d known before the Venmo requests began.
I met my boyfriend about ten years ago, and over the course of our relationship, his business became increasingly successful. We were traveling nonstop, living in multiple residences, mostly in Europe. I had a really great job working in social-media management when we first got together. But once we started traveling so much, he asked me if I wanted to quit and he would support me. He offered me an allowance of about $4,000 a month, plus the use of a credit card. I said “yes” because the company where I was working had become very toxic.
There’s this stay-at-home girlfriend, trophy-wife dream that you’re sold, and it felt like I’d achieved that. Of course, my dumb ass never thought of how that could turn out badly. I thought it was love. He was always clear that if we ever broke up, he’d make sure that I had some money, too. I wouldn’t just be left hanging with nothing after I’d quit my job to be with him.
You’d think I could have saved money in this situation, but the $4,000 a month went surprisingly fast. It costs a lot to hang out with rich people. They always want to eat at expensive restaurants that I’d never go to in my regular life and have multiday theme parties that require all these different outfits. You waste so much money.
Soon, things started going south. I checked my boyfriend’s phone one night and found out that he was talking to a really young girl on Instagram. We had one big blowout fight and after that he was like, “I’m done.” He sent me an email about our breakup deal — it was basically my severance package. He said he would pay out my allowance for three more months and give me $250,000. Which sounds pretty great, except he never paid me the $250,000.
I moved back into my parents’ house in Canada in the middle of nowhere. I felt like an alien. I understand why people get trapped in these relationships because they get used to a lifestyle. They can no longer imagine living without what they have. And I certainly felt that way. I mean, I didn’t grow up with much. I had worked in factories and at McDonald’s. I really didn’t want to go back to that.
Very luckily, I was able to get a new job with my old company. Still, I couldn’t let it go — like, how am I going to get the money that was promised to me? My ex wouldn’t answer my calls and didn’t want to be in contact. But he also kept telling people that we were still together. It was very confusing.
Eventually, I called a friend of mine who’s a psychologist, and he helped me compose a diplomatic email to my ex. And that actually did work: He sent me a quarter of the money. Then we kept in touch, and a few months later, he gave me the second quarter of it. He was kind of stringing me along, but also, I missed him. We met up in person a few times and hooked up. But I knew I couldn’t trust him.
At one point, we got into a huge argument. He was drunk, and I was so angry at him. I screamed at him, “You don’t keep your promises! You never even gave me the money that you offered.” And he drunkenly transferred me all the rest of the money in the middle of that fight, right then. It would have been a relief if it wasn’t such an awful moment.
From time to time, he now asks me to give it back. I think he feels entitled to it because we still travel together occasionally. In fact, we got back together for a bit and then never officially broke up. I’ve used most of the money to set up an entirely new life — move to a new city, get a new apartment, rebuild my career. I have about $100,000 left at this point, about three years later.
I know it was dumb, but I lent my then-boyfriend — now my ex — $5,000 to buy a new car. His old car had just broken down, and he’d gotten a great new job that required him to be in the office, starting right away. Lending him the money was my idea. He told me he’d pay it back in installments, $1,000 a month, once he got his new paycheck.
He was a trustworthy guy, or so I thought. I really wanted to help him out. He’d had a bad run of luck: His mom was sick, he’d gotten laid off, and he just couldn’t catch a break. We’d been together for two years and we were talking about moving in together.
The $5,000 was from my savings account — in fact, it was most of my savings — and I banked on him paying it back pretty quickly. But then, a month later, I caught him texting with an old flame. He swore it wasn’t anything serious, and at first I believed him. But then he did it again, and I could tell from their messages that they’d met up in person. I was devastated.
We broke up, and he said that he would still pay me back. He’d paid me the first month already, and I still have his texts to me saying that he’d continue with the planned installments. But then he didn’t pay the second month. He had excuses: He said his mom needed money for medication, which she probably did. Another month went by. I really didn’t want to deal with him anymore. So, finally, I threatened to take him to small-claims court. I think he thought I wouldn’t actually follow through with it. I’m a teacher, and I didn’t want to have a public court record — it’s embarrassing, and I didn’t want it coming up if someone Googled me. But finally a couple of friends came over with a bottle of wine and helped me fill out the paperwork to file a claim. They still call me Judge Judy because of it.
Luckily, we didn’t actually have to go to court. Once my ex got notice of the claim, he started paying me back. He still hasn’t paid all of it, or even in the amounts that he promised — it’s $400 here, $600 there — but he’s been Venmo-ing me every month. He still owes about $1,500. I’m annoyed, but I also feel like I dodged a bullet. I mean, what if I had kids with him or something? What if we’d actually moved in together? $5,000 is a lot to me, but it could have been so much worse. I don’t want to say that I learned a lesson; I hope to find a guy who I can share finances with someday. But it sucks that I trusted him and it blew up in my face.
I have outstanding Venmo requests that my ex hasn’t responded to for over a year. He owes me about $1,000 total. It’s not going to ruin my life if he doesn’t pay me back, but I’m annoyed that he’s ignoring it. He reaches out to me and acts like things are normal, as if there isn’t this outstanding debt.
We were together for over four years when I lived in San Francisco, and we were friends for several years before that. So we have a lot of shared history. During the pandemic, we wanted to move in together, and that’s when mortgage rates were incredibly low. He was like, “Why don’t we just buy a house?” And once he got that in his head — this milestone of being a homeowner — he wouldn’t let it go.
At the same time, I was working at a company that got acquired, so I got a lump sum of cash. That put me in a position where I actually could afford a down payment on a house. My mother definitely thought it was a bad idea. We weren’t married, and we didn’t plan to get married anytime soon.
My ex was incredibly successful financially. He worked in tech, and he never spent aggressively. So he definitely had the means to buy a house with or without me. Eventually, we found a place that we really liked, so we bought it together, put the deed in both our names, and split everything 50-50. When we went through the mortgage process, the bank looked at his financials and told him, “Oh, you don’t even need another person on this mortgage.” They barely even looked at my paperwork because of how good his was. But we split it anyway. The house was $1.25 million. We each paid half of the down payment, which was $115,000. And then we split the mortgage, which was $8,000 a month.
My ex was incredibly resistant to change and confrontation. We were in couples therapy for a while. Finally, I realized that certain issues would always be there, and if I stayed in the relationship, it wouldn’t make me happy. But then I had to figure out how to get out of it. Owning a house with him made that significantly more complicated.
When we broke up, we’d owned the house for two years. I was like, “Okay, here’s the deal. I’m going to do a sublet in New York for a month, and I’ll give you some space. And then, when I come back, we can get ready to sell the house.”He said he could make that timeline work.
Of course, when I came back, he still wasn’t ready to leave. I offered to help him pack.I offered to help him find a new apartment. I’d been paying my half of the mortgage while also paying for a sublet in New York, so I was losing patience. Finally, he showed me all this math he had done in a spreadsheet and was like, “This is how much money we’re going to lose if we sell our house right now. I think we need to wait until it’s a better time to sell.”
I stayed in New York, and he stayed in the house. Once he finally agreed that it was a good time to sell, I did all the work of getting the house prepared. I hired the landscapers, the painters, the flooring people. My ex and I had a shared bank account where we would put our money in for the mortgage and pay for other shared costs, but sometimes he would forget to put his share of the money in, so I would cover it and send him a Venmo request. And there’s still two outstanding things adding up to $1,000. You can only remind someone to pay you one time and then the request just sits there.
He reached out about something recently, and I was like, “While I have you …” and I sent a screenshot of the Venmo requests. And then he just stopped responding.
Then, two weeks later, at 2 a.m. his time, he sent me a playlist on Spotify with no context, a bunch of love songs. I didn’t respond. Then he sent me another song a week later that reminded him of a concert we went to. Again, I didn’t respond. Then, he sent me a picture of a piece of mail addressed to me that got delivered to his new apartment. It was very clearly junk mail, but he was like, “Do you need this?” And I was like, “No, throw it away.” And then he was like, “Oh, hey, how are you?” And I was like, “Listen, I’m not trying to be rude.I don’t like ignoring you. But I did send you a text message asking if you’re going to pay me back, which you ignored, and then you continued the conversation when it was convenient for you.” Which is always what he does.
He scrambled and was like, “Oh my gosh, sorry, it’s my ADHD, I totally meant to go look at our Excel spreadsheet to make sure the calculations were right.” But that was 22 weeks ago at this point. This man still has not gotten back to me.
Throughout my life, I’ve worked for different arts organizations and theater companies. I’m also an actor and a playwright. I’m proud of my work, but it’s challenging financially. I’ve been on food stamps and Medicaid. I need social services to cover my basic necessities. I recently got a grant to help pay my utility bills. It’s always been challenging to be an arts worker, but especially in the past couple of years, there’s been a lot of cuts to arts funding.
I met my ex about three years ago and we really hit it off. I was ready for a serious relationship. From the jump, he was very much like, “Oh, just let me take care of everything.” He made so much more money than me that it was hard to say “no.” He was asking me out for dinner and taking me to events and things that I wouldn’t be able to afford on my own. I met some of his friends and they were like, “Just let him do it. He’s rich.”It felt nice to be wined and dined, but it also made me a little uncomfortable. I’m not from a background where I’ve met a lot of rich people — if anything, it’s always been the opposite. But he seemed to really respect my work and want to be supportive of it.
A few months into dating, my rent went up and I had to move. He offered to help me, and I was like, “Oh, sure,” thinking that he’d help me pack boxes and carry stuff. But then it turned out he was offering to help pay for movers. That made me realize that he lived in a different kind of reality. I’ve helped a lot of friends move. I think it’s normal to put in some elbow grease to help people you care about. But he wasn’t actually going to put in elbow grease — he was going to pay someone else to do it for him. I declined.
About a year and a half into the relationship, a couple of my contracts dried up. I was also dealing with an ill parent, and that required some unexpected travel. I was really stressed about my finances, taking on extra gigs wherever I could. And that’s when he was like, “If you need help with your bills or rent or anything, just let me know.” Finally, I took him up on the offer. He paid for a full month of my rent — which was cheap, under $1,000, but still, that was a huge weight off my shoulders. And he said, “You don’t have to worry about paying me back. It’s all good.”
At that point, he had also bought a house and invited me to move in with him. But the house was outside of the city, and I don’t have a car. He offered to get me a car, but I said “no.” He also offered to put me on the deed of his house, and I was like, “Don’t do that. I have student loans and we haven’t been together that long — this is kind of fast for me.” Everyone in my family was like, “He sounds like a keeper!” And I was impressed that he was making his intentions known. But I also didn’t want to move.
A few months later, I was still struggling. I didn’t want him to pay my rent again, but he kept offering. Finally I agreed to let him pay for half. Then a similar situation happened a few months later. And again. He gave it all freely and said it wasn’t a big deal, but to me, it was a lot of money. I didn’t want to rely on him, but I was living under the poverty line and he was making over six figures. I realized that I really needed to find a pathway out of this trap that I’d gotten into. I applied and got into a teacher training program that would give me my master’s degree in education, fully funded, along with a small stipend.
At the same time, we started having some conflicts. If I ever had a concern about something, he would get defensive and behave in a sort of entitled way. Like, “Oh, I take care of you, I look after you, and you’re going to be upset about this little thing?” He seemed to feel like I didn’t have a right to be concerned about anything.
Around that time, a play I wrote got production funding, so I got a space to perform it. The venue was outside of the city, so my ex gave me a ride and helped me set up. But the whole time, he seemed really grumpy about it and was rude to some of the other volunteers. When we got in the car afterward, I was like, “Are you okay?” And he got extremely defensive. He was like, “Why do you care so much about these volunteers? You don’t even know them. Don’t you see I’m doing so much for you?” And then he started bringing up the money. Like, “I just paid your rent for you. You don’t appreciate me.” It was late at night, and he was driving, and I was starting to get scared. So I just tried to de-escalate. I was like, “I’m sorry. I appreciate you, I really do. Can you please just pull over?” I was crying. And that’s when he broke up with me. He was like, “I guess you’re going to say that we’re never going to come back from this.” And I was like, “Yeah.” A friend came and picked me up and got all my stuff at two o’clock in the morning.
In the days after, he was texting me all the time, calling me names, harassing me. He wanted us to get back together. It was just not healthy. That’s when he told his family that he’d been supporting me financially and that I’d emotionally manipulated him. They accused me of financial abuse. And I was so upset about it that I told him I would pay him back. I don’t want this karmic weight on me, feeling like I just took this money.
If I ever knew things would go this way — that it would create this power imbalance where he would feel like he could treat me however he wanted because of his financial situation — I never would have agreed to his help. I would have figured out another way, like I always have before.
I can’t afford to pay him back now. I told him that as soon as I could, I would. I have no idea when that will be, and I feel really conflicted about it. I really don’t want this money between us, hanging over my head. Overall, it’s more than $4,000. To me, that’s so much money, but to him, it’s not. Sometimes, I’m like, Is this a fair exchange?
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