I've been dinged about 3 times where I've lent significant amounts of money to people. It took me about 3 times to learn my lesson. If any of my close family needed money, I'm not expecting it back. If I get it back, great, but at least I'm not counting on it. Anytime anyone ask me to borrow money now, I just say "things are tight and I can't afford it."
The problem is, I'm one of those guys that comes across as a really nice guy so people try to take advantage of that. No more lending money for me...