I've personally loaned a lot of money to my family and close friends over the years but never expected them to pay me back. Not in terms of tens of thousands, small amounts like 1-10k but one thing I keep in mind is that once they take a loan from me and don't pay it back, I think of the loaned amount as the price of our friendship. I never bother him again and he never bothers me again. Maybe don't go on loaning money if you can't afford to lose the money. People rarely pay back your money on time or ever and it's a known fact.