This is the second time we've needed to lend money to the same friend. He's a wonderful person and is in a bad situation (cleaning up his parent's financial mess, which is messy in part because of his mother's disease). He's hard-working, trustworthy, and so forth. We are glad to do it, truly. And he doesn't ask casually...it pains him. But this time was a little more than last, and it got me thinking about The People's Court. :haha: Over and over and over: put it in writing! But I could no sooner ask him to sign something saying he is borrowing x amount of dollars and will repay than I could chop off my leg. So my question is, do TRUE FRIENDS AND CLOSE FAMILY MEMBERS really put these loans in writing? Have you ever been involved, and if so, how is it not horrible awkward and or insulting? I would honestly just prefer to lose the money than say to him, "Sure, we can lend you the money...but could you just sign this first?" If I didn't trust someone to repay a loan, I can't see myself ever agreeing to it.