This post is for you if:
"But Mattyanon, if I could just meet a nice girl to fuck, I'd have all the friends and motivation and money and I wouldn't have these problems"
Nope - doesn't work like this, it's the other way around.
You need to have a good life FOR YOURSELF. If you want women, they'll want to see that you have friends and are respected. Women do not aspire to meeting a guy with no friends, no social skills with no friends. This means that socialising is first (which is good because you want it for yourself anyway).
This post does NOT cover meeting women. You might meet women socially as a result of this, you might not, but we're not going to cover meeting women in this post. Think of socialising as a pillar of your life. Other things go on top of the pillars. Women are the bit on top of the roof. But you need the pillars.
I feel/am awkward
I can relate... this post is what I've learned over decades. I've been at the bottom... in fact worse than most of the people reading this. I had negative SMV at school. I'd have been better off invisible.
Feeling awkward is concentrating too much on yourself, and not knowing WHAT to do. If you knew what to do you wouldn't feel awkward. So you're going to learn what to do.
You're going to have to put aside your own feelings about yourself and your awkwardness. IGNORE THEM. Do not focus on them - instead focus on who you're talking to, the conversation, the situation. As you learn how to actually do this, you'll feel better about it all.
Don't define yourself as awkward. Do not say "I am....". This is defining yourself and holds you back. Instead say "I sometimes feel awkward when...." but ideally just say "I am going to learn how to do X by trying it".
In friendly environments people are very open to being friendly. NOT in bars: these are actually semi hostile in many ways. But in environments where people aren't drinking, have a common interest and are likely to see each other again, people are remarkably friendly and easy going. You're the outsider though, so you have to do 75% of the work.
Maximise your looks - short term
Looking unclean, badly groomed, rough clothes makes others feel uncomfortable around you. There is no excuse for having a bad haircut. Sort out your hair, your face, your clothes if you need to. If you have money get good decent clothes and shoes. If you're balding trim it right down: combovers look pathetic, trimmed or shaved looks strong.
Maximise your looks - long term
I shouldn't have to say this around here, but I will: you need to lose weight and hit the gym. If your bodyfat is >10% then you can do better. Women like slim predominantly and muscular second. Fat with muscles is less attractive than slim. What applies to women applies to men: men know attractive when they see it and it does get you a measure of respect. For friendship (not women) you can get away with excess fat, but you really should be working on this as it benefits all areas of your life. If you're thinking "it's what's inside that counts", you have a long way to go.
"But mattyanon I'm a 4 foot dwarf with one leg, three eyes and a conjoined twin"
In this case you REALLY need to do what you can do maximise your looks. Swap that extra eye for a leg and lose the twin if you can.
Spend money on fixing anything you realistically can. It won't fix your problems but it will help. Certainly for meeting women: anything reasonable (less than $10k) you spend on yourself saves you money while dating in the long run. The more attractive you are the cheaper and better your dates will be.
Value
Be a person of value. This means showing/having talent. Hard work. Trying to do things. Passion.
Avoid neediness
No whining. No social taking or neediness (this usually takes the form of manipulating conversations to get a result you want, and people hate this but don't quite know why). If you're new to this: do not aim to benefit emotionally from your conversations. Go into them expecting to get nothing. Do not try to get something from people. Do not aim to get approval or even worse: sympathy. Do not complain about god damned anything. Before you unload your problems on people or hijack conversations: remember that other people have their own shit to deal with - it's not just you.
So you put aside expectations, sex, fears and negative thoughts about how people see you. And stay positive!
Speak fucking clearly
If there is one dealbreaker to quickly forming friends it is quietness, mumbling, speaking quickly, or speaking incoherently.
This creates misunderstanding, people hate saying "pardon?" and "what?" over and over again - in fact most people won't say this at all, they'll say something nondescript and move away from the source of the discomfort (you). So don't do these things.
Aim to be fucking HEARD. This is hard if you're shy. It's also hard if people your whole life have awkwardly avoided you. You don't need to shout, but speak slowly. VERY slowly. Speak to be heard by someone who is half a yard further away than the person you're speaking to. Speak slowly - practice this with someone you know if you can. Slow it down. 10x more than you expect.
And speak simply. It's very hard to follow complex sentences from someone you don't know. Slow it down, speak up, and convey simple things. If you need to convey complicated things then break it down into smaller sentences. Don't run it all together. Don't worry, people will give you chance to get your point across - ESPECIALLY if they can hear you clearly and you're smiling.
Smile and eye contact
Eye contact should be around 90% while you're speaking, and around 50% when you're listening.
Smile if you can. I know the tendency is not to smile when
Find ways to socialise
This has to be something IN PERSON where you meet and interact with others.
Ideally it's on your mission (you have a mission, right??). Ideally it's something you're passionate about. But that's not essential, because the aim here is to be more sociable. This will take effort and it's scary, but this is doable for anyone with $20 per month spare and can leave the house. This is probably you.
Here's what you do: join a club or group or activity or something. Meetup has thousands of them close to you unless you live in a volcanic cave in Iceland. Women will be under represented in all groups you are interested in and that's fine.
This could be a tightrope group, a climbing club, an improv group, a public speaking group. Anything you're even vaguely interested in. Ideally it even helps with skills you need. Join a few. They're all different, but here's the simple secret of 99% of clubs you'll find: they always want to grow their numbers with people of value. And you ARE a person of value, because I've told you that this is who you are now, and you are now that person.
Whatever you do, NEVER say "I'm here to meet people" or "I'm here to socialise". That makes you look like a loser from the start. Instead say "I've always been curious about naked striptease skydiving, I did come to the right place I hope". Ok so that might not work for you, but "I'm curious about X" works fine.
When you turn up to most groups (in my experience) it goes like this:
First time: people will be friendly but slightly wary. They don't know you and most importantly they don't want to invest in you. All clubs/groups have a churn or newbies who don't come back. The way that you get round this is that you go straight back the following week.
Second time: now you're a regular, believe it or not. They've seen you before, you didn't stab them last time (hopefully), so now you can proceed with being slightly more friendly.
Making Friends - small but definite increments
Friendship can be cultivated. What you do is just try a little bit. Doesn't take much, but you have to try a bit, especially in established social groups. You basically do slightly different things that put you in more contact with slightly different people (sit someone else, go somewhere else, etc). Either you've joined a new group, or maybe you're walking a different route or sitting somewhere else in the company café.
So you see/meet a new person and you say "hi" (or whatever's normal for your group). That's it.
Second time you meet them you introduce yourself and get theirs and for the love of god remember it. That's it.
Third time you say "hi xxxx, I'm xxxxx again" [obviously use your real life name and don't say xxxxx. The reason you do this is because you know to make the effort to remember people's names, but they don't know to do this, and they'll be uncomfortable if they forget. Then you tell them something about your day, and let them do the same if you wish. In group settings allow other people to catch your name again for the same reason. If there's a "hi my name is X" badge, where this always even when you think everyone knows you. It helps people start talking to you.
The point of this is that you keep it short and simple the first time. The second time a bit more, and so on. It's like a video game: first you do level one. Next day you do level one and level two. Next time you do level one, two, three. (Err... obviously don't keep introducing yourself).
Making friends - continuing
After that you put in whatever effort you think is necessary, being careful not to be too friendly with eager losers who have no friends, looking for commonalities, but always expanding your circle.
If you're seen to be having fun and positive interactions with people (doesn't have to be anything over the top) then more people will be more friendly and open to you in future.
It's actually really simple, but the steps and the gaps matter. It's very comfortable for everyone. You're not aiming to go from strangers to best buddies in 20 minutes. It's more like gradually increasing steps.
Men bond through shared experiences, or building something together, or trying to achieve together, or by competing. Do things you want to do and bond with the people you meet doing it. It's basically the only way to do it.
Women at groups and clubs
Do not try to flirt before you are fun/popular: this will come across as creepy, so just don't even try it yet. Until you know what you're doing with the basics of being social, do not cling onto the women, do not try and flirt, certainly don't ask them out.
Women rarely make good friends for a man, so don't aim for much here. Women can sometimes be easier to be friends with, but do make sure you spend longer with the guys because that's your aim here. You don't want to be fucking a girl at your favourite group, break up with her, and then have all the problems that follow from there.
Conclusion and motivational "you got this, buddy" bit
This all might not seem possible, but it really is. I've learned all this without the benefit of this article, so you can do it much faster than I did. You can be social and even popular, and from there you can leverage that into talking to girls. This is gonna take a while, but you can do it. You got this.
TL;DR How to tackle all of this
I've covered a lot of ground here as concisely as I can, but let me tell you the secret to mastering it:
1. Actually get out there and do it. I give you permission to fuck it up as many times as you like.
2. Concentrate on mastering one bit at a time. Get that down and move onto the next.
3. Ignore setbacks. That's how you deal with setbacks: you fucking ignore them, got it?
It's not easy, but it is doable. Get out there and do it tiger.
How to break up with a LTR
This assumes that:
Agree to meet in public
Agree to meet in a public place with secluded areas (eg quiet coffee shop). Women can be unpredictable when their ego is hurt and being dumped is an ego bash for anyone. You want her to have to maintain a level of decorum.
Be clear with her
First tell her it's over between you. It's important you state this first. No wavering on this. Use words like "xxxx-girl, it is over between us". No apology, no hesitation. Lack of clarity about the change of arrangements will just increase the hurt and confusion.
Then tell her very roughly why: tell her it's not working for you, it's not what you want. DO NOT BE DRAWN ON DETAILS, say things like "I've made up my mind" and "it's not working for me" and "this is not what I want". Note that this is blame-free but without details. No matter how good your reasons are, this isn't the time for recriminations.
Do not negotiate
DO NOT ALLOW ROOM FOR NEGOTIATION... first she'll press for exact details, then tell you how she'll change in this area, and therefore you don't need to dump her, that she deserves another chance, etc etc. Don't go down this road, don't give details, don't negotiate.
If things are going badly, you can leave at any time. Don't forget that. You've delivered the news up front, so you can just say "I have to go" and walk out if you feel you're wavering, if she's getting too emotional, if she starts lashing out, if she tries to negotiate too relentlessly.
She'll suggest you remain friends, and you enthusiastically agree to this. This will make her feel better. Of course don't actually do it because male-female friendship is one-way and will drain you. You need to get her out of your system and to get on with your life.
Stand up, give her a quick hug if she's amenable, say something like "best of luck" and then get on with your life.
You owe her nothing
Remember this: YOU OWE HER NOTHING. Drum that in to your head before you see her. Most likely you've done far more for her than the reverse, she isn't somehow entitled to your continued help and support. You don't owe her a relationship, don't let her make you think you do.
After that she'll likely try to maintain a high level of contact (ie maximum girlfriend privileges but without sex)... you should gradually fade this out (ie increase the time before responses in order to create healthy distance).
If she goes all stalker (ie making any sort of threats against you) then you cut her off entirely, and ignore ALL contact. The only way to ditch stalkers is to give them absolutely zero response to any contact they make. They almost always fade away over time.
Bonus: optional continued fucking
If you want to continue fucking her (and this is frequently possible), then this has to be done AFTER the new boundaries are clearly agreed (this needs at least a month with no or almost no in-person contact). If she lashes out at you in any way due to the breakup then cut all ties - continuing to fuck her with no relationship isn't going to make her behaviour improve.
DO NOT FALL BACK INTO BOYFRIEND MODE.
Do not be her texting buddy.
Fuck a few other girls before you go back to avoid oneitis.