I was socially awkward all through high school...so I know where you are coming from. Then at some point I became a superstar. It made me think about what was different about me from before.
First its going to take hard work and consistency to succeed in anything, including finding a chickee chick (or dude, whatever)
Whats do I think makes the difference?
Confidence. It makes you better at everything. And girls (all people to some extent) are programmed to like confidence. When true humble confidence is not around, they will take cockiness instead, but definitely prefer the first. The male/female thing developed certain proclivities like this because she would be vulnerable while pregnant(and while child is young) for a long time and needs to feel safe enough to do that. It doesn't currently hold true, as women do not need men to safely raise babies, but thats the root of that attraction to confidence.
No body likes doing the mental work of being around someone that is not confident. Its such a drag to hang with someone and feel sorry for them because they are not confident, and they are looking at you for reassurance every minute.
Confidence is when you are sure you can handle whatever, but are not threatened or bothered by being told a better way or the right way to do something. Cocky freaks out when corrected.
Know you are a cool in your own way, and unique and why you would make an excellent match for some girl. the more confident you are, the more confident you will feel, and it builds upon itself once you get the ball started. So one of two things are true for you now. You have skills, mentality, and most importantly you like of yourself, to allow yourself to be confident, and just by realizing this you are able to start to do so. Or you just cant be confident because you feel you know this or that is wrong with you.
Hopefully you just need to decided to be confident. Deciding this, will literally make you better at everything. You can allow yourself to be confident because actually doing it will make you more effective. It may be simple as understanding that truth. If thats the case your done, be confident, go out and about and it will happen. Is being confident scary, yes, you are putting yourself out there and might take a tumble here and there.
Its actually a crutch, a coping mechanism to not be confident. It shields you from defeat, "See i knew i couldn't do it" feels better than i thought i could, but i am now wrong and defeated. Feels better to be right and defeated.
If you feel something is wrong and cannot allow yourself that confidence and thus make yourself even LESS effective and amplifying what you dont like about yourself to you and other people. Its illogical. Lack of confidence is worse than whatever you dont like about yourself. but one option is to do the hard work to fix it. everything is fixable. But its hard and its much easier to pretend you cant fix it.
learned helplessness is a physiological trait of all humans. It has a place in nature, if you tried to get this really good fruit, and a bear lived there and you failed, you wasted tons of energy for no yeild. Thus it is important not to waste your time again for that food source. But now, its a curse. We are so lucky to live in a way that we CAN fail, over and over and its fine....it is how we have advanced so far as humans, because we had the cushion to fail over and over and not die of starvation. your posts says to me you may be suffering from learned helplessness with meeting people. At least a little. its not 100% yet because you wrote this post, but then pattern is right there in your words. you are basically saying, I have failed up until now, I fear i may fail forever (unspoken-should i just give up or keep trying i am out of ideas) But watch out for learned helplessness.
Also, online dating sites are great because are so many people looking. Just DONT lie, DONT find a picture from 5 years ago when you were superbuff or otherwise more desirable than you are now. Be honest about what you like, how much you would or would not respect a partner. say here i am flaws and all. Then, what hits you get will be good ones and you will feel no need to hide. in fact the first dates will YOU deciding and trying to root out if they lied, cause you know you are all upfront. The balance of power shifts. That very fact may make you feel less on edge.
And dont be an ass, respect everyone the same, including women. Women get a raw deal in our society. If there is a girl in a "mans job" she must be better than most of the men doing it. Exceptional at it actually, or she wouldnt be there. They are expected to wear makeup and shoes and dress cute and all this stuff. Feel lucky you are not expected to do all that our society. However hard confidence is for you, its ten times harder for a girl. so respect them, they dig it. acknowledge the silly sexism of society and dont be a dick.
You could always move to Los angeles or something. I got fired in West Virginia and was on unemployment, not finding work, and saved it and planed and used that time to move to Los Angeles. Something about moving to a new place is very liberating, and gives you a little more swagger and life experience to draw from and learn you are capable of surviving and gives another reason for confidence. But my mental confidence shift happened when i failed out of art school. I learned how to "liquid dance" or "pop" and it got me into shape and taught me a lot about learning something very very foreign to me.
That being said, getting healthy an into shape is a win-win. I started lifting weights when I was 31 and it doesnt take much, as long as you are consistant, to get results that make you healthier and more confident that you may be desirable for female. Its not wholly true, because looks are not the primary attractor for girls over 24 or so, depending on the girl, they grow out of that sometimes way earlier. If your under 270 lbs and clean you meet the criteria for 95% of mentally mature girls, and thats what you really want anyhow. But if it makes you feel "sexyer" for lack of a better term, then you will be sexyier because:confidence is everything.
And you would be a good catch. I bet you would not cheat on a girl and just be there for her since you know what lonely is. You would probably realy really emotionally care for a girl....and that is what they need. Confidence is what they want. Emotional support is what we all need. Alot a girls have been with dudes that didnt give them emotional support, and useing "Nice guys" for the emotional support of the relationship while being "girlfriends" with some emotionally absent jerk is a thing girls do. It is the cause of the misnomer "the friend zone" because "nice" guys allow themselves to be emotionally used. but thats another rant all together! lol forgot i said all that.
hopefully all this will get you started, i am almost fatigued from writing so i must bow out or get sloppy and incomprehensible, but to sum up.
Be confident, if you cant allow yourself that, you already know what you need to change. Research and do the hard work and effort( risk failing and starting over thus wasting that effort and start over) to improve that aspect of yourself. Then be confident, pick and choose what ladies are right for you.
One last thing, if you are in a situation and have the chance to talk to a girl, you have nothing to lose, you didnt know her before, and if you fail you still dont know her. You lost NOTHING and gained social xp. everytime there is a random girl you are guaranteed to gain something from trying to talk. Dont try to bed her,lol, dont put that pressure on yourself. Just try to talk an meet her. and if you dont get very far , you gained xp. and if she happen to just come out of a relationship with some dumbass jerkwad, she may be attracted to someone treating her human and being friendly and she might be ready to try to hang out with and see what respectful smart guys are like. cause you are part of the smart crowd if you enjoy the challenge that is dwarf fortress.
TLDR; if this is something to skip to the TLDR for, then you are not willing to put in the effort to make significant change and are just posting for social proof that you should give up.
Actual TLDR; Be confident, you like dwarf fortress, you must be smart and are a good catch.