I've done most of the things people have mentioned--shoplifting phase, killed a frog and was traumatized, injured a younger (quasi) sibling, stood by while others killed or tortured animals, took actions that could have (but did not) lead to the death of a cat, was a dick/bully in junior high (like, bad) followed by a year-and-a-half guilt complex, split town at eighteen and left my sisters to fend for themselves in a multi-dimensionally fucked up situation, embezzled food, exploited a crush for sex (though the crusher wouldn't really take no for an answer), lied for no reason... other things, probably. For a decade or so I couldn't decide whether I felt guiltier about not ending my mom's boyfriend when I had a 'clean kill' than I would have felt for killing him, but at this point I stand by the realization I had in the moment, that ending the man would not have ended the causes and circumstances that brought him into our lives.
The one that stuck with me most is kind of trivial. When I was seven-ish, I had a neighbor down the road a year younger and a bit slow--he may even have had a mild expression of Downs Syndrome. We played together along with the only other guy around our age in the 'neighborhood' (five or six houses within a mile or so of where a dirt road peeled off the state route). He had decided I was his friend to probably a greater extent than I had decided he was mine, and asked me to go with him to his dad's doctor appointment a couple towns over. His dad was in his sixties and had health problems.
"We can play airplanes!"
It sounded like the dullest, awkwardest possible way to spend three or four hours. I never said yes, but I hemmed and hawed and made excuses about asking my mom, and he just plowed ahead with, "We can play airplanes!" It came to the point that he and his mom and dad pulled alongside the road to pick me up, and I begged my mom to go down and tell them I wasn't allowed to go, but she said she wasn't going to lie for me and I had to take care of it myself. So, I went down to the road and told him flat-out what I should have told him two or three days before (or just sucked it up and played airplanes), "I don't want to go."
He wailed. I believe his exact words were, "I hate you, you stupid-head!" repeated several times in different orders. It hadn't hit home before then that he was asking for help, that he didn't want to sit in a waiting room and worry about his dad, and instead I was making things worse for him.
So yeah, even though later in life I would bring people to tears for fun and to get attention, being a bad friend to the slow kid down the street is what stuck with me.
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