Petty Cash is a weekly advice column where the experts (plus a millennial InStyle editor well-versed in pettiness) weigh in on your awkward and annoying financial faux pas.

DEAR PETTY CASH,

So, my ex boyfriend owes me money — quite a bit of money, actually. We dated for a year-and-a-half. When we first met, he had a great job at an agency and was living with roommates. After two months, he moved in with me. It was a mix of timing (his lease was ending), convenience (it cut down his commute), and new love (we could spend even more time together). Fast forward another two months and he decided to quit his job due to creative differences. At first I was proud of him. He valued his own integrity more than a paycheck. But then his savings dwindled and he hadn’t secured another job.

Luckily I have a great career and a decent savings, so picking up the slack wasn’t really an issue. In my mind, this downturn wouldn't last forever and someday he’d be making much more than me again and it would all even out. That’s why I had no problem shelling out over two grand for us to go on vacation, or covering his half of the rent month after month. We broke up in January but he wasn’t able to move out until early March. All in all, my ex owes me over $4,700. Over the past six months I’ve shared a document with him noting the expenses that I’ve covered on his behalf. He said he’d pay me back as soon as possible.

But he seems to have moved on and forgotten any responsibility he had towards me. He has a new job, he’s dating someone new, he booked a trip to Europe for the fall, he got a new tattoo, and has been going to different events around town that I know aren’t free. I confronted him about the fact that any expendable cash he has should be coming my way but he always comes up with some excuse. I feel used, and I’m at the point where it feels toxic to keep him in my life in any way. Is it worth keeping a connection with him to get my money back or do I just cut ties and chalk it up to the cost of bad relationship decisions?

FOR ME, ONE OF THE WORST PARTS of processing a breakup isn’t the sadness, or the loss, or the anger: It’s the regret and psychological self-flagellation that takes way too long to banish from my brain. The decisions I made to support and maintain the relationship — decisions I was once confident in — all transform into a series of ugly, stupid mistakes I convince myself I deserve to be punished for. Remember all those times I chose the other person over myself? That was fucking stupid. How about the moments when I compromised on something I wasn’t totally comfortable with? That was also fucking stupid. And who could forget all of the weeks/months/years I wasted with that person, when I could have been doing literally anything else? Yep, fucking stupid.

Confronting the fact that you’ve invested something in another person that you didn’t see a great return on is truly one of the worst parts of breaking up — and in your case, there’s actual money involved.

But what if you just forgive yourself for that? Try to let go of any regret you might feel for lending your ex money in the first place. Sure, you didn’t come out and explicitly say that you’re feeling regretful, but the fact that you said you feel used and are also keeping tabs on his new life lets me know that you are struggling with how everything shook out. Deep down, I truly believe that every decision made out of love in a relationship is one made in good faith. Good relationships don’t exist without compromise. Each compromise makes you less of an autonomous person, and therefore, vulnerable to the other person. Vulnerability is brave, and in good relationships, intimacy is our reward for taking the risk.

However, in a bad relationship, where one person is taking more than they give, compromise and vulnerability can turn you into a lovestruck piece of Swiss cheese, forming hole after hole until you feel like there’s nothing left but a small, yellowed and slightly hardened rind of the person you were before. And when the other person finally leaves, that vulnerability turns to weakness that we weaponize against ourselves. And so I say this as someone who has been there, and who knows many someones who have also been there: No matter how foolish you feel, you were acting from a place of love and support, and you can feel proud of yourself for that. If having the courage to love and support another person without guarantee makes us dumbasses, then by all means, let us be dumbasses together.

But just in case “be the dumbass you want to see in the world” isn’t the strongest possible advice for you, I consulted with both a financial literacy expert and a licensed therapist to see how they’d handle a money-owing ex.

Interestingly enough, they both said the same thing.

“If I were you, I would reach out one last time and give him a deadline,” says Catie Hogan, a financial planner with Element Financial Group in New York City, and the author of The Millennial’s Guide to Getting Your Sh*t Together. “If he doesn’t pay up, then you need to cut your losses and move on. You could take legal action and chase him down, but that’s going to cost you more time, money, and emotional stress. Do you really want to do that? Losing $4,700 sucks a lot, but consider it his parting gift. Give yourself a clean slate, and stop following him on social media so you don’t drive yourself crazy looking at pictures from his trip to Europe with his new tattoo and girlfriend.”

Michele Koury, LMHC, a counselor with Know Yourself Counseling, echoes that same sentiment.

“Write one more letter asserting what you're owed and maybe even outlining a proposed payment plan — but then cut the losses and take this as a lesson in boundaries, especially since your job provides you with financial security. You’re still giving him your time and energy, on top of the resources you’ve already drained. It’s not healthy — and it’s way too easy to focus on the money, thereby delaying the necessary mourning-the-relationship stage of healing.”

What their advice — and mine — boils down to is this: If you really feel like you want or need to get that money back, start by outlining everything in writing and proposing a repayment plan. You could also speak with a lawyer and have them draft a letter threatening legal action. If you really, really wanted to, you could even pursue that money in court. But given your financial situation, something tells me that you could choose a far easier route to closure in this situation. Yes, it really fucking sucks that you will probably never see that money again. However, so does clinging to the last remaining tie that the two of you have, a tie that he seems to be completely unconcerned with acknowledging. It’s time to let go — of the money, the regret, and ultimately, the relationship. You’ve spent long enough thinking about what he owes you. Now it’s time to think about how much you owe yourself.

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