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I lent someone 500 dollars to pay off a speeding ticket. I did it knowing that I would never see the 500 again. Not because I didn't think she was good for the loan, but just because that way I don't have to worry about hounding her for it. I think she has paid most of it back.
Only loan money you don't want back just in case. Oh and your friend sounds like a jerk. Save that money to do something fun with other friends.
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This too shall pass.
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