Dear Tineoidea,

This whole situation certainly made me introspect a lot and I can see how I should cut less of a slack to some people. I’ve hurt my own self-respect many times while trying to mediate with people who don’t want to put any effort into it.

Good you’re realizing it. The reasons for this behavior probably lie in your childhood, but we don’t need to talk about it if you don’t want to. Important is that you realize it’s been harming you, and that you seek to change it.

I’m not sure if my relationship with him can be salvaged or rebooted at this point and I’m not feeling much desire for it.

From what you’ve written so far, your friend is quite toxic and pretty unaware and unwilling to own up to his mistakes. Why would you want to go back and be bitten again and again? In my opinion, he would need to undergo a profound change to deserve your friendship again…

When it comes to her though, I’m willing to give it a good try as long as she offers a genuine apology and wholeheartedly tries to build the trust anew.

It’s a good attitude. I hope she’ll see through him soon enough… I wonder how much you have shared with her (before it was too late) about your friend’s character? Did you warn her about his possessiveness, his reckless behavior and your resentment towards him, or you only had positive things to say about him (in the months preceding the conflict)?