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I too think this was a scam. I can say if I were ever in the guys situation I would not be driving around blockbuster I would still be at walgreens asking people there if they could help me out and be certain to exchange info so I could pay them back. More likely I would sell something I owned or offer to work for the assistance.
I do have to say I have been guilty of giving money to panhandlers but feel I try to make an educated guess as to the reality of the situation. For example I was outside of a construction site on break and a guy asked me and my co-workers for a few bucks each and while the other 6 guys gave him some cash I asked him what it was for and he told me beer to stay warm. I of course told him to get lost although my friends thought I was a jerk. On a separate occasion there was a guy who was very dirty and had a bike with what appeared to be all his possessions on the back he was holding a sign that said will work for food, this guy seemed legitimate to me so I gave him $40 as I had no work for him. This guy looked as if he was going to cry and thanked me profusely while being obviously chocked up and humbled. Now I guess this could have been a scam and he could have done something else with the cash but I feel like it was genuine. In short I think use your gut and do what you think is right but in the op's post I fell he did an awesome job interpreting the situation.
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