This is the best answer. People are all saying "you give money, don't loan it" much of this is probably the christian revival thing "jews do it so it must be bad". It doesn't follow. [Edit- This is like a leftist saying "it's an unplanned donation".]
A gift was not the arrangement you made, it was an interest free loan in a time of crisis. Milky Meat OyVey has the best answer, try to work out a payment plan. $100/month isn't bad, and he can pay it off in a year.
You're not being a bitch, it goes back to the highschool days when you'd lend someone $5 and ask for it back and they'd say "it's only $5 bro"... Yeah, well, if it's only $5, it shouldn't bee too difficult to pay back now should it?
If he doesn't pay you back or gets angry that you're asking for a payment plan then you've found out that he wasn't as good a friend as you thought.
At this point, just make sure that whatever you ask for it's concrete like "$75/month until it' payed off" not "pay me something monthly".
I had a guy tell me to get a job when I asked him to repay me. I've never had the chance to put the screws to him properly. I'm thinking something involving his spine.
I had a guy tell me to get a job when I asked him to repay me
oof.... He's lucky if his teeth weren't loosened.
It was a small debt. Even at the time. Not really worth it at the time. Now nothing is worth it, so hitting the guy repeatedly with a hammer just seems like a decent use of time.
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