Money is a difficult subject for some people to talk about. Even worse is the assumptions we make about those who have it, or those who don't or have made poor decisions. Lending money is arguably even more of a challenge to bring up whether you're asking to borrow it or you're asking someone to pay you back. What end of the spectrum do you land on when it comes to lending out your hard earned dollars to someone? I used to not really care until recently. My sister in law and her husband had their car repossessed a while ago and I decided to lend them a bit of cash to get it out of repo. It wasn't much. About 150 dollars. My wife's cousin had loan them the rest - Closer to 400. Weeks went by with no communication on where they were at in terms of paying me back. This was after I was told it would only be a couple of weeks. Then I see them eating out at restaurants and going to the movies and the zoo. I get it. Even when money is tight you need those escapes from everything. After a few ignored text messages I finally got a response and they gave me $20.00. This was back in May I believe. It's now September and I haven't seen another dime and again, no "hey sorry things are really tight right now." Needless to say this has left a sour taste in my mouth. Am I being an asshole for thinking I'm entitled to some sort of communication? Perhaps they're just embarrassed and don't want to discuss it. Either way, it's mildly irritating. I'll live without the money but at the same time, things pop up for us too and it would definitely help out. Anyways, have you had any bad experiences lending people money or is it something you just don't do? Oh and as for my sister in laws cousin? He moved to China and also hasn't seen a dime.