My personal rule is that I never lend money to friends or family unless I am prepared to consider it a 'gift' (i.e. yes, it is a loan but one I'm fully prepared to forget about as to not cause other grief). This rule for me basically means I don't lend out large sums of money very often, and then only in very specific cases like the one Ken mentioned above (a family emergency type deal).
The good news is this had led to me never having to worry about it - I lend when I think it is ok and if I get it back, great. If not, I'm still good with it. Incidentally, I think I've always gotten it back except for perhaps a few very small amounts that just got lost in time ($20 that I never saw again type things).
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