Rahx, I'm late to this and I'm not going to go through the play-by-play of your last encounter, but Valkyrie, Jack, et al are dead on when they say that learning how to accept what's in your control and tempering your expectations accordingly will be the greatest asset to you.
Among other things, it sounds like you need to expand your horizons beyond your current group of friends. One of the great things about forming new connections is that you get the chance to be something new to someone else. A significant part of your identity is caught up with your relation to them and likely has been for a while, which, evinced by the comparisons you keep making, probably hasn't done you much good in the process of your development.
It seems like you're putting in the work on exposing yourself to new people, but your self-loathing is preventing you from extracting the lessons that would serve you best. Keeping on the grind is the right move, but you have more to address with yourself if you want to grow in the way that you're longing for.
That starts with learning how to be kinder to yourself, my dude. You are profoundly negative and seem like you have some untreated major depression. I'm not sure what your access to resources looks like, but you need someone more intimately attuned to your life to get guidance that feels satisfying and actionable. If I were you, I'd also speak with a psychiatrist and get started on a treatment plan.
Right now, your self-esteem is far too enmeshed with milestones that you haven't reached. I'm not you, but I do know what that feels like and that it can be overcome. I promise that unless you work on yourself in earnest, the goal posts will keep moving and there will always be some kind of albatross on your neck.
If you want, you can PM me and I'd be happy to share a few more things that I think would helpful for you and assist in finding some mental health resources in your area.
Can't say it's particularly surprising that Jack has explosive anxiety and abuse of meds for said anxiety issues
Also, absolutely fuck off with this. This is a wholesome thread. Thank you for sharing your experiences, Jack.