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I've personally never lent any significant amount of money to friends. Even after reading the responses in this thread, if it was a close friend and he/she desperately needed it, I'd still probably try to help out. Of course, I'd be pretty clear in what the loan payback terms were up front, and I'd probably try to make everything airtight in some sort of legal contract. Maybe I'd try to find some sort of collateral, too.
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