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If I had 2k I'd do the same thing I always do when this situation comes up.
1) Make sure I won't miss the 2k.
2) Loan him the 2k but with terms of X payments of XXX and when.
If he pays you back you will know that you can trust him. If he doesn't it's well worth $2000 to find that out. I'd make sure to be very clear that I do expect my money back and set a no b/s deadline.
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