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Every time I've seen someone less fortunate at the time when I wasn't one of the less fortunate (heh), I would give whatever bill happened to be the first I grabbed out of my pocket or wallet unless it was just $1, then I'd look for a bigger denomination. This might sound crazy to most, but during the years I was doing this I would "justify" it by comparing it to what I'd buy with that and realize they were in need of it more than I.
This came to a halt when a friend of mine gave a homeless man in NYC a $20 just out of the goodness of his heart, then the homeless man was searched by a cop on-foot outside of the establishment and there were drugs found on him. The cop then was accusing my friend of a transaction, rather than a donation.
-JM
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