First things first I just wanna say thanks for taking the time to read this if you do, and possibly helping out.
I'd post this to another sub-reddit but I trust the opinions of seddit more, especially with these issues.

Backstory time - I grew up with the bundle of stuff that contributes toward being an "AFC". Family issues, no dad growing up, a (recently changed) older brother, and bullying in school in some form or another.
I was a virgin until I was 19. My friends shamed me for it daily up until I lost it, which probably didn't help with my anxiety around sex. Which funnily enough stopped me from getting some more than a handful of times.
but it all changed around the time I was 19, before I had lost my virginity.
I changed areas in work toward one I knew I would enjoy more. Immediately around knew people, I knew it was my chance to change. I watched the "fake it till you make it video" just previously, and did just that. It worked amazingly.

Over the next few weeks after that it was like I finally "found" myself. I got involved with great looking co-workers (generally not advised, but I was a bit of a douche thinking back). Everything I did I felt like a pimp. For once in my life I didn't give a fuck. About socializing, about anything.
After a few amazing months of being a boss, I got involved with an ex-coworker who had heard about my adventures. She just walked up to me and hooked arms with me while we were switching clubs. We did the deed, and started seeing each other for around 2 months, it was great.
She was kinda boring, but fuck it. She was hot and I was clueless. So I was gonna ask her out, to be my girlfriend or whatever.

But I fucked up, I got royally drunk and started calling her different girls names, phoned her 18 times after she left me in a club with our friends. Y'know, the usual.
So we "Broke up". Boo frickin' hoo right? Well I was actually depressed for a few weeks, if not a month afterward. I suddenly went reserved and all that again. Started thinking there was something wrong with me, and fell down this slippery slope of over-thinking EVERYTHING.
And here I am a few months shy of being 21, I know so much about female attraction, life, social situations because I've over thought them all, that I actually feel clueless. Also everything that goes wrong around me is always my fault. According to my brain, anyway.

I actually read a bit of red-pill stuff which did not help at all with life.
I actually over-thought so much, that I think about what I'm thinking is weird. It's like there's this self-doubt always hanging over me.
My social skills have greatly improved over the past few months but I still don't feel confident, don't have the self esteem I had before.

If you could piece me any advice I would appreciate it so much.
Like what do you guys think about on the daily grind to work? Not even joking, I spend my time thinking about what other people think about, or what they think of me. Obviously putting people on a pedestal and making myself feel worse. I'm literally a totally average dude, with some pent up frustration over myself.