To Avoid Repaying $1,500 He Owes Me, My Roommate Invented A $1,000 “dog-sitting” Fee And Sent It By Certified Mail

He was one of my closest friends (close enough that my card was linked to his Apple Pay because he was constantly short on money). When we first moved in together, I loaned him $3,000 to help cover move-in costs and the first month’s rent. Over the next six months, he only repaid about half — and only in small amounts, always after I reminded him multiple times.

I kept swallowing the “I don’t have money” excuse, even while he was buying a huge TV, redecorating his room, and going on vacations with his girlfriend. But now something happened that just blew my mind.

I had to leave town for 20 days. After a week of offering him a debt reduction to watch my pup (and getting shut down every time), I arranged for a friend to stay in my room and take care of pup for free. She was totally fine with it and happy to help.

He immediately refused to allow anyone else in the apartment and said he’d kick her out if she showed up. Then he suddenly changed his mind and said he’d do it himself — after blocking my free solution. I told him clearly I wasn’t hiring him — I already had someone who was happy to do it for nothing.

A few weeks later, he sent me an official certified letter demanding $1,000 for dog-sitting and said he wouldn’t repay me unless I subtracted that amount from the debt.

That was the final straw. Now, I’m determined to take him to court. It’s not even about the money anymore — it’s about the betrayal.

I’d really appreciate any advice — especially if you’ve been through something similar or know what kind of evidence actually works in small claims court.

Location: Florida, Hollywood

UPD:

Quick clarification (since many seem confused): – Yes, we are both on the lease. – Breaking the lease early would cost around $8,000, which I would have to pay alone. – He refuses to be removed from the lease and won’t agree to replace me. He's very comfortable that I'm paying and almost do not live here - yes I use ChatGPT to translate

I really appreciate the perspectives, but I’m specifically looking for legal reasoning, not general advice to “just let it go.”

If you know of a good book, case law reference, or even a legal weak point in my position — I’d genuinely appreciate it. On the flip side, if there are solid strategies to prove the debt or invalidate the “dog-sitting” claim, I’d love to hear those too.

I’m not here for emotional closure. I’m here to build a case — or understand why it may not be viable.