I feel like I need to summarize where I'm coming from before I can get into the question to here it is:
Quick bio: I'm 27 and never had a girlfriend; I'm a software engineer so I don't meet many women in my day-to-day life; I work out and have started training MMA.
I desperately did TRP style pick-ups when I was like 24, which got me laid a couple of times but it was SO MUCH WORK for some lousy hookups, I abandoned it and tried to improve my lifestyle instead. I find "gaming" to be self-compromising and a horrible world to live in. There are so many drunk and desperate or fucked up people out there, it's not worth the scars.
My mental state: I'm aware of all the misandry and privileges of women in western society. I used to hate them and thought they were pathetic, but I'm coming around to the notions of masculinity vs. femininity and I see that women are just doing their thing and our hyper-feminine culture has made me disgusted with it and myself for falling victim to it.
I've read No More Mr. Nice Guy and am actively trying to change the way I think and behave.
I'm about to start reading Models by Mark Manson.
Okay, so that's it. Now onto my question:
I keep falling into the trap of going out on weekends alone, drinking myself silly and "trying" to meet women. Of course what happens is that I go out, drink a lot, maybe dance and say stupid things to random people, and basically gloss over every woman I see. It's like I want to meet someone and make intimate connections, but I take one look at them and go "no thanks". If I do end up talking to girls, I don't really impress them. I'm too unhappy and insecure to have fun interactions.
I don't really signal my intent for intimacy and sex; partially because of my Nice Guy syndrome. I feel like it compromises me. When I talk to girls, I literally just talk to them.
Mostly, my problem is that I'm insecure. I'm too afraid to just walk up to girls and start talking to them, or it feels like too much work, when all I want to do is relax and have fun. I also always seem to meet guys who are in the same boat as me, and we team up for the night, and none of us ever actually do anything. I can feel them lose respect for me as the night goes on, because they think that I'm going to get them girls (I'm relatively handsome), and I don't.
What I end up doing is standing around the bar, half in, half out, and hoping something cool happens.
Every weekend I realize that what I'm doing is pointless and self-destructive, but I don't want to do other things like going to art/theater classes or trying to chat up girls in coffee shops. The mere thought of doing that for the sole purpose of meeting girls makes me feel gross.
I feel depressed and trapped.
What the hell do I do in this situation?