The issue of loaning money to friends rarely comes up but whenever it does I do. I can't say I'm a sucker because I've never been taken - yet - but then again who is the bigger fool? The fool or the fool that follows him (that is, himself, exaggerating his foolishness more so for tempting fate for the fourth, fifth.. fifteenth time).
Quit while your ahead? There really is no such thing. Ahead, behind, you quit when your done and not one second earlier or later. Ask a gambler.. these things are just in the cards. Regardless, I ain't holding any aces. Guess I'm left with hope on this one. Keep your fingers crossed.