I lent money to a "friend" for an emergency car purchase. That was 15 years ago. I never got it back. I was very resentful about it for a long time. My therapist made really good points. First she said that I might be out the money but every time that "friend" drives that car they will remember they got it on false pretenses. It's better to be the one not paid back than the one who didn't pay back. Second she told me, in the future, think of money loaned as money gifted. That way, if I get paid back its a sweet surprise and if I don't, well, it was a gift. I just thought I'd pass along words that helped me.