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I've got a couple regulars I'll drop a $20 every once in a while (if they're going to use the money for booze/drugs they might as well splurge and if not they might as well splurge).
Otherwise I sometimes give in response to good patter but mostly it is a polite no if they speak to me or just walking by if they're passive. More common is if I have something on me (say the doggy bag from a group lunch) I give it to them.
When I was younger I used to call the bluffs of people with car problems by offering, instead of giving them money, to take a look at their car. Amazing how often, when we got to where their car was it had apparently just been towed. Did that once with Lani along (told her to wait, I'd be right back) and she still hasn't forgiven me so I don't do it any more.
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