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I've done the same thing before... and I've only been taken up on the offer once.
About 2 years ago, it was maybe 10pm and my wife and I were in resort town just wandering around a few places. It was a very active area and this older guy, maybe 60 wandered up and asked if we could spare any money for food.
Our first thought was what everyone else thinks - you want it for booze. So, I said, we are more than happy to help you, but only if you go over to that store (it was small supermarket type of place you see in a beach town) and let me buy you some food.
The guy smiled and said "I'd love that and appreciate it so much". I think my wife started to get misty eyed at his response.
Anyway, I think we bought him $20 worth of stuff... and as we sat at a bar across the road, we looked out about an hour later, there he was on a bench. Eating the food, drinking the water and putting the rest in his back pack. Whether or not he traded some later for booze, I dunno.
But, it was a good deal.
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