Well now, let's see what I can dredge up... I was one of those "good kids" growing up, so the list won't be very long. If anything, I tend to feel bad for things that simply aren't my fault. (The guilt card got played by my parents a fair bit growing up, so it's part of my personality now, I guess...)
Growing up, until like 9th grade I only had the friends that were even more loners than I was. And I was quite the loner. I'll be honest, they all had reasons nobody else was friends with them. One guy in particular had a bad reputation about him, though I don't think it was ever confirmed, that he stole stuff. He did always root through our closets when he came over to my house, and ask about things he thought we didn't want, so it seemed plausible enough. Around middle school though me and a mutual friend decided to just tell him enough was enough. I don't remember it clearly, but he moved away soon after that. I do feel a little bad, considering I didn't know his full story.
A little later in high school, one of the better friends I'd made wanted to drop out of high school, and I can say I didn't try all that hard to stop him. Last I heard from him he was doing some sort of alternative GED thing, which is good, but I still should've tried harder to get him to stop.
Here's one I beat myself up over often, and I can't even explain it. I had a summer job as a cashier at some point, no big deal. I failed the Sting though. If you don't know what that is, they set it up to see if you'd sell alcohol to a minor. I remember asking for ID, seeing he was underage, and then... letting him go. Not as a conscious choice, I was on autopilot, but it still baffles me. I saw his ID, I knew he was underage, but somehow it didn't process! I paid a fine, lost my job and all that, so it's not like I got away with it, but I hate myself for that. It's bad for the self-esteem too, makes it hard for me to trust my clearly flawed judgment.
Finally, one of my current best friends... well, it's a long story. Suffice to say that he does pretty idiotic things, like drive too fast, drink absurd amounts of caffeine, and go on occasional drinking binges. Thankfully he's smart enough not to drink and drive, but he's totally reckless and thinks he's invincible otherwise. I just worry eventually his luck's gonna run out. I've tried to get through to him, to no success. So for a span of about 6 months I'd managed to convince myself that I'd "given up on him", and held a grudge against him. Still kinda do. It's just so frustrating... but I know yelling at him doesn't help. Mainly I feel bad that my genuine concern turns to anger when he doesn't listen. I can see the same guilt patterns my parents showed off in my relation with him. That long grudge, my distancing myself from him and my occasional outbursts? They were all supposed to guilt him into changing his ways. It's just... an unhealthy mindset to have.
...well, there you have it. I often berate myself for not being a better person, but those are my genuine screwups. The rest is just an unhealthy mixture of perfectionism and guilt.
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