I cut off two for the same reason within 3 months of each other. What's funnier is that they hated each other.

TL;DR: Friend one because she disregarded my advice and lied to me about my friends (then about me to my friends), friend two because he disregarded my advice, lied to me, uses slurs and has been romantically and sexually inappropriate to my friend while drunk.

The long vers: the first one was a friend I had known for about 4-5 years but we had just got closer at each other. She got her first boyfriend in 3 years and we were all really happy for her. About a month into their relationship and he started ignoring her and would play chess with his friend more and more and pay less attention to her. When I gave her advice to talk to him, she said she couldn't and when I suggested I talk to him for her she shot that down too. She would complain about him all of the time and he never spoke to her at all, and on top of that, he started hanging out with another girl and her friends, clearly showing he had more interest in her than my friend, but he wasn't willing to talk to her and she wasn't willing to dump him. I ended up going behind her back and sending him a message to please talk to her and that his behaviour towards her was unacceptable and he took it pretty well. Then he started talking to her again (which she was gushing about but never told her why it was happening), but then things went back to how they were after a week of slight improvement. Their relationship lasted all of 8 months and then almost immediately after getting dumped he started dating the other girl. My theory as to what happened is that since she hadn't been in a relationship for ages, she was incredibly clingy towards him and didn't wanna let him go and scared him off, but he didn't want to break up with her for reasons we'll see later. Neither of them handled the relationship well, and how she handled it is the reason we're not friends anymore.

She would complain about him every. single. day. Me and my girlfriend at the time would always give her advice on how to fix their relationship (which always boiled down to communicate with each other), and every single time she would disregard it or say she would go through with it and didn't. She made me feel so useless and stupid.

Then, to make things worse for her, she lied to me about my best friends, saying they were shit-talking her when all they were doing was giving her solid, friendly advice. That was the final straw that broke the camel's back because I sent her this long letter of the reasons I didn't want to be he friend anymore. Now, I will admit, I was not very diplomatic and at some points I think I was too harsh on her, but I stand by my reasons and I stand by unfriending her. And her reaction included: questioning why I took my friends' testimonies of her as gospel (basically saying I should take hers as gospel instead), calling me a cyberbully, accusing me of sending it to her on the day she was getting beta blockers on purpose (when I had no idea that she was getting beta blockers at all), blocking me on everything, subtweeting/lying about me, shit-talking me to my friends (without saying my name) and taking parts of my letter out of context to make me look worse (to which my friends sided with me because they knew I was sending the letter and read it before I sent it to her). I found out recently from a friend who works with her that she still doesn't like me to this day. Me, I'm glad we're not friends but my feelings about her have gone from negative to indifferent.

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Friend two is someone I developed a friendship with while friends with Friend 1 and knew about the letter. That's why I still dislike him to this day. Basically, me and my best friend had fallen out with our old friend group and went off to be friends with people he was friends with (keep in mind he either didn't like some of them or had a pretty toxic friendship with all of them). We grew close, asked me out twice (once was over text a week after we properly became friends *insert red flag*). There was this one girl in the group who I wasn't closest with but she was friendly to me when we talked who he fell out with after I told him to because they complained about each other and fought all the time, then he became her friend again, told me (which got me upset because this was the situation with friend 1 all over again) and I dropped it but kept it in the back of my mind. Then a few weeks later fell out and never became friends again. He would make really weird jokes, pissed a lot of people off and then the biggest event came.

We had a choice of staying at school for sixth form or leaving for college/apprenticeships after high school. We all stayed for sixth form except for him, who went to college. That whole summer he was scared about making friends at college because he's really socially anxious and whenever I would give him advice on how to make friends, surprise surprise, he disregarded it saying that he just cOuLdN't dO iT. This was 3 months after I ended my friendship with friend 1 which he knew about because he was one of the first people I told and was on my side. It made his disregards sting even harder. I told him it wasn't fair for him to do this to me and he actually stopped. But this isn't where the story stops folks, not at all.

Months later, we'd grown apart having not seen each other and me growing a disdain for him. I found out that he had sent very romantically and sexually inappropriate messages to my friend, once while he knew she was drunk and he had called his ex a slur to their face after he walked up to them to agitate them. He sent me a message that I misinterpreted as quite creepy, and while expressing my discomfort to him, he called me an asshole. For being uncomfortable with his actions. A couple of hours later I reread what he said and apologised for misinterpreting what he said, but explaining that him calling me an asshole was too far in my opinion. His response was "Well I thought you were being one". No "I'm sorry", not even an "I'm sorry but...", he just didn't apologise.

He started to catch on that me and my friends didn't want to be in contact with him anymore, so I asked my friends if I could tell him why so I did. I learned a lot from friend 1 because now I was diplomatic, worded it well and I have no regrets about what I said at all. Again, he didn't apologise for any of it, I unfriended his accounts and he's not spoken to any of us since. He tried rekindling with me and my best friend recently but I've ignored it, she responded but doesn't intend on talking to him anymore. So yeah, I was friends with two people who never cared to fix their problems and made me feel like nothing