Seeing if I can pinpoint a problem to get better at this

TL;DR: seeing if anyone can help me pinpoint what's wrong so I can correct it, cause I don't have a freaking clue.

Hi there everyone, what's up? Alright here's the deal. I suck at talking to women, aproaching them and specially suck at all that having confidence thing. And I really wanna improve, I finally hit rock bottom and I set my mindset on improving, thing is I don't have a clue on how.

Let me give you some insight first: I'm 23, had a really intense albeit short relationship. As a teen where I should've been dating and all that stuff I just didn't. Had really low self esteem and no confidence at all, really didn't thought anyone could find me atractive, plus I was the "weird" kid that liked all the stuff that nobody else liked. Now since I had a gf part of that is gone, but I still really don't have much confidence and I don't know how to talk to women (specially start a conversation) unless set up by a friend or someone.

In fact the only reason I got a girlfriend before is because we were mutually and heavily attracted to each other. We just looked in our eyes and everything flowed naturally. I don't know if because of that I just knew the exact things to do and say, or it was that because that attraction, no matter what I did it worked.

I don't thinkg myself as particulary ugly nor pretty, but somewhere I still think sometimes that it's hard that others would find me attractive (liking a shit ton of girls on tinder, only getting 2 matches of which only 1 talked didn't help much tbh). I come out as immature sometimes because I'm saying stupid stuff all the time, but that's just because I love to laugh as much as possible and make others laugh (I think maturity has nothing to do with the things you use and do to have fun/entertain yourself), I'm the one that jokes around all the time and tries to keep everyone laughing in my group of friends. My friends told me I'm good at making others laugh, and with just that is enough to get it going with a girl, but I still find it difficult (and the depressing days just impossible). I'm by no means a lady's man, going to a bar or a club and picking up a girl is completelly out of the question, never been able to do that. And when others encourage me to do it, I just shrug it off saying I'm not in the mood or some lame excuse like that to not embarras myself.

I'm not shy or anything, as matter of fact I can talk right away with people I don't even know, and tend to get along with everyone, but I when it comes to picking up girls, or talking to someone I like I just can't do it. The only exception is when I'm crazy mad about someone, I seem to go on autopilot. I just want to recreate that whith anyone.

So, I really wanna change that. Don't want to be a Barney Stinson but at least I want to be able to aproach a girl to pick her up. Just feel like anything I'd do or say to start a conversation out of the blue will come off as stupid.

I just don't know what to do. Women seem to naturally gravitate towards pretty much everyone I know.

Do you know if there is anything in particular that I can do to be better?

Thanks a lot, really, and sorry for the big ass wall of text.