They say it’s harder to break up with friends than a romantic partner since the rules are a lot less cut-and-dry. This often results in people tolerating others’ company they otherwise wouldn’t be around because they can’t bring themselves to cut them loose.
I’ve only ever friend broken up with one other person who was going down a 4chan bigotry rabbit hole back in the day, and he’d constantly bring up problematic talking points that I’d try to dismantle, but he was too dogmatic to have a conversation with so I had to stop being friends with him.
I check up on his online presence every now and again, but he’s only gotten more racist and sexist. Sometimes I wonder if having more pushback from me or someone outside whatever echo chamber he was in would’ve helped, but he just sapped my energy so much I couldn’t take it.
(trivia for older internet peeps; he was the Legorobot Comics author. If you ever saw his work you could probably tell he was gonna grow up to be a bigot)
Anyways, what’s your friend break up story? What was the last straw? What was the first straw? Any regrets?


Yes. Twice. So one was a guy who was sorta the center pivot of a group of friends. Its was kinda two groups that got together mine and his. I can’t even remember who sorta got the two groups going. It was like him, his brother, his neighbor, and his sister with boyfriend and on my side were some nerd/geeks that hung out. He was kinda a jokester. A loki type. Lovable jerk. Nothing he did was all that bad and we were definately the nerdy of the people he hung with. Anyway his sisters friend turns 18 and he just jumps on her. Not literally but basically takes advantage of her naivete and just uses her and dumps her. It was sickening. Now it was not the last straw and not immediate. It was kinda wierd because like I would not call his sister a friend. She and her boyfriend would once in awhile hang with us if we were there or playing a game or something. So she was the sister of my friend who was sometimes hanging. Then you know her friend was someone who was around to. So it was like my friends sisters friend. So its ot like I knew her all that well. Again though it was just so, ugh, for lack of a better term evil. Like it was like loki after he ate the witches heart. Just to far. Basically with college and such getting together was lessening and that just killed any motivation to make myself available. So it was just sorta an acceleration of drifting away. Strangely I ended up going to his wedding.
I think he was the first male I met who had the “marrying kind” philosophy which became a real red flag for future guys I met. Like later a guy I met in graduate school like a year or so into hanging with that group brought up the marrying kind in bro talk and sorta did the same thing there.
Now I have had a variety of best friends. One from grade school era, one from high school, and two from my various higher education days. The one from high school always kinda had this thing. I kinda have a personal moral code and well this guy didn’t. He respected I did though and sorta behaved around me. I think he thought of me as a good influence on himself. Yeah sounds wierd but its kinda my best guess. Its not like sussed this out when I first met him. Over time though it sorta became exhausting. You see it was like he was always trying to find my line and trying to get right up next to it. I think the thing he never got is there is a black line but its just the end of a deepening grey line that gets darker and darker. You have been in the recesses the whole time. Again though it was his relationship with women. He meets this girl significantly older and he asks me about dating her and im like I don’t see it going anywhere because of the age difference. He is determined and they start a realtionship. Which is fine because the girl is very cool if annoying in her own right. Anyway he starts something with her younger and better looking friend (who is one of those girls who seems to like to go after guys after they have been vetted by her friends) without stopping his thing with her. She finds out and he ends up dating her but that ends because he was never really quality. Later he rebounds to this nasty chick who uses and abuses him (which depending on how you look at it maybe he deserved). He complains about her but won’t leave her and she threatens to end it all the time which he bends over backwards desperate to keep it going. All the while he is looking for a replacement. You see he is one of those people who can’t handle being single voluntarily so he is always looking to upgrade but desperate as all out not to lose what he has. So he is constantly beating the bushes looking for another bird while hanging on as tight as he can to the one in his hand. Its funny because he was the same way with jobs. The better a job or person treated him the worse he treated them and the worse they treated him the better he behaved. All this was making me pretty sick of him. This by the way is also one of those folks that always has get rich quick schemes. Anyway one day he gets pissed at me so I took the opportunity to skate and not look back. The really kinda funny thing is he on more than one occasion sorta predicted that it would end like that. So he seemed kinda cognizant of how he was (and I).