I've got a really sad one from a couple years back.
After a movie at the local mall, I decided to browse the DS games at a Gamestop. There, these two kids.. had to be... 12 I guess, brothers, quietly and awkwardly approached me. With their eyes darting around and voices quivering they pleaded that I buy them a Leisure Suit Larry game. (Quite topical, as the infamous Quick Look video of a LSL game hit today).
I laughed, and said no on principle that it was a shit game. But they kept annoying me, so rather than let a scene occur, I was just like "fine, fuck it." I figured at least I'll have a story to tell a random forum some day. They gave me crumpled up $1s they had in their pockets. I was rolling my eyes and sighing, hoping at this point one of the passing employees would put a stop to it. They didn't. I bought the shitty $8 game with their crumpled up dollar bills, gave it to the kids outside, and some clerk out there thinks I must be some idiotic perv.
I'm hoping they got caught playing it later in the week and went "It's not our fault mom! Some nerdy white kid bought it for us!"
Also, reading a few of these posts reminded me of another: I bought myself Resident Evil 4 on my 22nd birthday, and was carded. I'm 26 and still get carded for R rated films today, so I'm kinda used to it. It was just made more awkward by the woman doing the math on my license and being embarrassed by her mistake. "ohh, heh, I'm sorry... you've got a babyface." All the unnecessary awkward dialogue made it a good Larry David moment.
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