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

[Anonymous]

Anonymous wrote: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?

Did you write up a contract when you gave him the money??

If nothing else, you should've jotted something down on a piece of paper stating the terms of the loan "I Larla Jones gave $5,000 (in cash & x points) on Sunday, July 10th 2022 towards paying off his bills. He is to repay me within 6 months time or legal action may be taken".

Sure he wouldn't have been happy you were making him sign it, and he would've made you feel badly & guilty (ie; "don't you trust me?") but you just tell him you've been burned in the past, and your lawyer suggested you do this for EVERY loan, no matter who it is for.

At the end of the day, I guarantee you that he WOULD have signed it because he needed the money.
He may not have liked it, but here WOULD have signed it.

No signature, no money... period.

He has no intention of paying you back OP, because if he did, when you gently broached the earlier situation, he would have told you... I need more time, can we make a payment plan, can I pay you in installments, etc.

Nope, what he did was excuse his need to repay with that itemized list.
If you haven't figured it out, that's his way of saying that you're not getting your money back.

Go on Judge Judy -- she doesn't accept dinners, groceries, movies, etc as repayments... not unless he specifically told you before buying each thing "this is to go towards my debt".
If he didn't do that, he can't change the terms afterwards.

She'll eat him for lunch and make him look silly in the process.

Don't EVER lend this man money again... and STOP paying for everything! Geez.

[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.

This.

[Anonymous]

Ask him for the 3k back in text. He won’t give it . Break up by text. Block and decide if you want to pursue in small claims court. Stop dating total losers!

[Anonymous]

I mean, you could take the appliances you bought. Assuming that is the portion that was points, but still.

[Anonymous]

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

+100

That money is long gone.