What's THAT thing that you once said or did, that you still cringe at to this day?

As a small child, say five or six, I told another kid on the playground that I disliked him because he was funny looking and had big teeth. I barely knew the guy, but my cruel insensitivity clearly hurt his feelings. In all honesty, he did have enormous teeth, and his head was a funny shape. I have no idea why I felt the need to point it out though. Just dumb kid things, I suppose.

Fast forward to the age of sixteen and I'm invited to a party. It turns out this same guy is the host, and I hadn't seen him since I was about seven, because we went to different schools and lived on opposite sides of town. We got chatting and he seemed really nice so we got on well. As the evening wore on I recalled all of the times I regretted being mean to him on the playground all those years ago, and after a few drinks, felt a compelling urge to apologise.

"You probably don't remember, but back in primary school I was really mean to you on the playground one day, and I said I didn't like you because you were funny looking and had big teeth. I want you to know that I'm really sorry I said that."

Turns out that he did remember, it stuck with him forever, and thinking about it made him very angry. He just couldn't ever picture the little shit that said it to him. Things turned frosty quickly, and despite repeated attempts to make my apology, I was told to leave.

I'm not sure now whether I regret saying the original thing more, or bringing it all up again for him ten years later. Either way, it appears that I'm quite the little fucker.

/r/AskReddit Thread