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Some of the details may be off, but the worst thing I can remember ever doing was in elementary. There was this one girl nearly all of the kids bullied, and I mean all of them, but I just kind of tried to avoid it all. One day after school, someone pushed her down the stairs. No one tried to help her, so I wanted to do the right thing by helping her up and get all her stuff. By the end, I promised I'd be nice to her from then on. Apparently, a ton of people had found out the next day, because my friends kept making fun of me for doing it. Eventually to get my friends to stop making fun of me, I told the girl to her face I hated her and for her to go away.
As I found out some of the details after she moved away of why she was bullied so much, I felt a bit less bad about it, but I still feel like a real jerk for doing that today.
There was also the time I conned a friend out of his Master Ball in the RSE days because I wanted an easy out on catching Latios or Latias since I wasted my own, but I don't feel as bad for that since it's just a game.