An old friend from high school is in a jam and asked for monetary help. He has gainful employment but his car took a major dump and unless he can get it fixed he can't get to work. He would be good for repayments, but it sure is a lot of money. $1k
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In this case, I'd worry about that red flag; I can see why someone might not want to be financially tied to their parents but to turn down the money seems a bit over the top.
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And if you do lend him them money, expect your relationship to change dramatically. It sounds like his parents are done bailing him out, and you would be his new sugar momma.
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I can see you lending him money if you've been in touch over time, but given that you guys have renewed contact a year ago via FB, it's kinda ballsy of him to ask for 1k.
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He has a lifeline, he's just choosing not to use it. Since he's asking you for such a huge favor, I don't think you're out of line in asking him why. That might make the decision easier.
If you do decide to help, consider the money a gift and assume you're never going to see it again.
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