O.o I would've given him the dollar, but taken it back the moment he asked for two. I get a lot of uncles and aunties asking me for money to get a bus/train home, so I'm used to giving them my spare change (I must have that kind of face or something), but I don't like people asking for a mile when you give an inch.
As for him picking your pocket... I'm going to give him the benefit of the doubt too, as I don't know if 60 year olds are nimble enough to be pickpockets.
I probably would have given him the $2, simply because the card is, after all, worth $30. But I think I would have felt very disgusted with him instead of being appreciative.
It's just a practical issue: you wanted the card back, you had to give up $2 for it, guy wanted a quick buck. There's no way to tell whether he was a thief or not, why not forget it. :)
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As for him picking your pocket... I'm going to give him the benefit of the doubt too, as I don't know if 60 year olds are nimble enough to be pickpockets.
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