What's the worst you've ever messed up?

I never really had an abundance of friends when I was in school, so I cherished and greatly valued the ones I did. And just over 2 years ago I ultimately shattered my friend group and it has caused me so much pain.

I had just got out of a 5 year relationship that lasted through high school, college and the start of my first real job. I met my close friend's girlfriend a month-ish after the breakup and we connected instantly over gaming and metal and stuff, became fast friends. She started coming to me about their relationship issues, and I kept insisting she speak to him (trying to be a good friend.. Ironically). Before they broke up she asked if i thought her and I had a chance if they broke up. I said I didn't know and would only do it if he was cool with it but was honestly pretty uncomfortable with the idea of it, even if I was in full rebound mode.

They broke up only a monthish after I met her. I felt she was kinda coming onto me a bit beforehand (coming onto me before she asked if we had a chance, it was obvious after that) and afterwards, and I was ultimately and honestly kinda lonely. Plus, she was a gamer, metalhead, attractive, and was into me. I was pretty insecure and I didn't think I'd ever have that combo. Stupid reasons, but there they were. So a week after their breakup, I ask him if he's cool with her and I dating. At first he says he doesn't love the idea but won't stand in the way and would tolerate it. So her and I get a little close, and a couple days later he changed his mind and decided that no, it was actually a pretty big deal and breach of trust. I understood, said okay, and backed off. But only for another couple weeks. She kept advancing despite that and I did a lot of thinking and didn't think it should be that big of a deal. Her persistence and my thinking broke me down so I told him we decided to date. He acted mostly nonchalant throughout it all, but i found out from another friend that he had some choice words for me. Well-deserved words, mind you. There's a fair bit more to the story (the 3 of us ended up living together for a few months, it was arranged before this all happened... I moved a couple hours away for work, he got a summer practicum in that same town so we were gonna live together, then her and I got together, then the summer came and she got kicked out of her apartment... Ugh... I was blind and fucking dumb) and in the end, she cheated on me anyway (should have seen it coming really) and caused a whole world of more pain. So then I didn't even have most of my close friends to help. He and I have only just kind of started talking again. We game together a bit, and have ironed it out. He laughs about it now, years later, but i still feel so bad and stupid. He acknowledged she was emotionally manipulative (she ended up with him a month or two after a multi-year relationship too) and has just moved on. I've only just started to move on.

I lost a few close friends for a few years over something that wasn't in the slightest worth it. I'm lucky that they're willing to try to repair it.

/r/AskMen Thread