Ugh, think I learned the hard way not to trust certain people with money...
loaned someone almost 800 bucks and they're skirting around trying to pay me back.
I don't loan money to friends and family. If I can't afford it I can't afford to help and I say, "I'm sorry but I can't afford it at this time. Is there any other way I can help?" Or, if I can afford to help they get it without expectation, and it will either all come out even in the end or it won't. If they elect to pay me back or do something for me later on, or maybe I need help somehow somewhere down the line and they help me back, fine. If not, it is what it is. I don't feel like I'm holding up my end of the bargain for a friend if I'm not willing to help them when I can afford to.
Learned that from one of the first friends I made in college who practiced the same thing. I don't know what his life experience was before that at such an early age that taught him that, but I truly think it's an invaluable lesson.