I was and still am going through a lot with anxiety/depression and as of 10 months ago i started my transition from male to female. He new a lot about this, especially since he was the only one of our mutal friend group that i trusted with these things. Who he was when he was with just me vs the friend group was complete opposites. When it was just us he'd always go on about how much it pissed him off the way everyone else treated me and that he was going to say something to them and stand up for me since i had a really hard time doing it myself, instead of doing that he'd join in on the collective shit on my life sessions kicking me when i was already down or trying to make me feel bad for not wanting to do anything because i was feeling like i couldn't handle it due to everything i was going through. I should have bolted much earlier(we'd been friends for about 6-7yrs) but the final nail in the coffin was when we took a group vacation where i got to be belittled for 5 days straight in a foreign country with a nice dose of transphobic shit thrown on top. After that i cut contact with them and they didn't even care so hey it sucks but i'm much better off without them, i don't really need immature man children in my life who lack an ounce of empathy for the feelings of others.