I had a similar scenario to yours, Tick, outside a Marillion show back in '89. We went to New Haven, and a kid came up with the sob story, needing "anything we can spare" for gas... my buddy gave him $10. We come out of the show about 3, 4 hours later, and the same guy walks up with the same story. I thought my friend was going to take back his $10 in spleen he was so pissed off.
I for one hate those scenarios. There are too many ways to make it "not a scam". I learned this in Philly; it got to the point that when someone would say "Hey can I have a couple dollars for food?" I'd say "I'll bring you a sandwich; what do you like?" More than half the time they would demur or ask again for the cash so that "I wasn't put out". Once, outside a Dunkin Donuts, I said "what kind of donut do you like, and how do you like your coffee?" and the dude said "I've already had four donuts today". Wha? Then again, I tell the story of the homeless guy I gave my Wa-wa breakfast sandwich to and he handed it back and said "I wouldn't eat that shit, and neither should you!" He was legit though; he was always at the same place, in his wheelchair with his buddies, and a couple cops I knew well knew of him and knew his history. I compare that to the two people - husband and wife - that would panhandle off one of the exits on 95 and she would show up with manicured nails, and he showed up one time wearing a $200 embroidered Flyers jersey. Supposedly, though, you can make decent bank panhandling; up to $400 or $500 a day in the right spot.