Had a friend 2 decades back, we were playing in a house poker game. He ended up losing around $500, didn't have the money to pay on him. I told him I'd cover his losses since I was up about that much, so I simply didn't collect that day and told him to pay me directly whenever he had the $. (So essentially loaning him $500.00). After 6 months, I finally asked him to pay. He barely paid $250, little by little (I'm talking 20 to 50 buck payments) and then had the nerve to tell me "As a friend, I would've expected you to forgive the rest of the debt." I told him, really? And as a friend I told him that I would be ashamed to let a debt linger and not repay (he wasn't broke or anything, far from it in case you're wondering.) Needless to say, after this, I terminated our 6-year friendship immediately and it was only on a casual hello basis when we crossed paths. First and last time I gave money to anyone.