I have given lots of money over the years to strippers, waitresses and hookers. The only thing I can say about it is most did not pay me back, and I'm convinced every last one of them needed it. I've rarely known any who were not broke all the time, and if they weren't, they sure as hell lived in shitty apartments and drove POS cars. Most strippers, waitresses, and hookers I have known have never actually asked me for money other than fee for service, which I feel is a perfectly honest transaction.
I really don't care that I have been ripped off because if I were in a desparate situation, I would hope to get a little soft hearted sucker to help me out, too.
The smartest way to do it, I've found, is to go through your synagogue, though. Just tell the Rabbi you are helping someone out and want to give it to through the synagogue (church) and have them give it to "an unfortunate" and at least you get a deduction from the tax man for your charity. Probably a tad sneaky, but who cares?
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