Asking for loan repayment in a productive (and hopefully peaceful) way

[Anonymous]

I loaned some money to my boyfriend to cover some unexpected expenses. The total is close to $5,000, but I am willing to accept $3,000 (the other $2,000 was in frequent flier miles/hotel points, so no real cash value, although I could have used those points for my own use).

It’s been about six months, and I don’t want the loan to drag out much longer.

I casually asked about it about three months ago, and he blew up me, including giving me an itemized list of how much he paid to take me out, or money he spent on groceries that I ate. Since then, I have picked up every check (that $$ obviously isn’t included in the loan amount).

I am scared to ask again, and I think this relationship is probably ending. But I would like to make an attempt to get my money back.

Any advice on how to start/have this conversation?

[Anonymous]

Break up, move out. You’ll never see it.

[Anonymous]

He is never paying you back. I would just cut your losses and break up with him, and consider the $3k a sacrifice for the benefit of learning early on that this guy is of poor character and not long-term relationship material.

[Anonymous]

Do you have anything in writing about the loan? Even texts or emails? If you do, dump him and take him to small claims court.

[Anonymous]

Anonymous wrote:Break up, move out. You’ll never see it.

We don’t live together (thankfully!).

[Anonymous]

Anonymous wrote:He is never paying you back. I would just cut your losses and break up with him, and consider the $3k a sacrifice for the benefit of learning early on that this guy is of poor character and not long-term relationship material.

Thank you. I needed to hear this.

[Anonymous]

Anonymous wrote:Do you have anything in writing about the loan? Even texts or emails? If you do, dump him and take him to small claims court.

I might. I definitely have receipts for things that make no logical sense I would purchase for myself (appliances installed at his house, spring break expenses for his child, etc). But he could argue these were gifts, I guess.

I think PP is right: write it off, and move on with my life.

[Anonymous]

For 5k you will never hear from him again. Dump

[Anonymous]

You need leverage. Tell him to pay or you will reach out to his family to let them know you are breaking up because he owes you money. Or whatever you think might work and you're comfortable with.

[Anonymous]

Anonymous wrote:You need leverage. Tell him to pay or you will reach out to his family to let them know you are breaking up because he owes you money. Or whatever you think might work and you're comfortable with.

PS And obviously break up

[Anonymous]

You got off cheap and easy, this is the best five grand you’ll ever spend; Summer is here no better time to meet someone new.
Neither a borrower nor a lender be.

[Anonymous]

Holy crap, this can't be real.
DTMFA as Dan Savage says.

[Anonymous]

I would try to slowly borrow it back. If it’s an ego thing and he can’t acknowledge he borrowed it, maybe you can appeal to the part of him that wants to be powerful and in control — he may “lend” you part of the balance.

[Anonymous]

OP I’m sorry you’re going through this. Good for you for having clear eyes about it though.

[Anonymous]

This is why you don't loan money to friends, family, or romantic partners.