Some of the things that have worked for me:
* Find extroverted people you can tolerate, they can introduce you to a lot more people.
* Find the groups of people who have problems with the tech/startup world but are still interested in tech (Who I'm assuming you're one of), there's a lot of people out there like that and you'll have a lot to talk about.
* If you're not great at conversation, try to focus on just being with people, say something like "I don't really have a lot to say, but I appreicate the company". Find people who want to just be around others.
Then this: http://www.mindtools.com/CommSkll/ActiveListening.htm
Focus on learning to really listen to what people say. IMHO that's generally the most important and underdeveloped social skill, the rest will follow.
I was once very shy, and decided to change. It took work, but people I know today think I am the most outgoing person they know. They simply do not believe I used to be terrified to talk to other people. I also used to think no one liked me. It just so happened the vibe I gave off was to stay away because of my shyness.
Even a few sessions can do a lot to point out your blind spots, give you objective feedback, and drill down on questions that you subconsciously avoid asking yourself.
I hated bars, so I figured I'd go to a few just to get out of my comfort zone. A couple girls offered to buy me a drink, big ego boost. Get used to being around people and interacting with them.
The end result is that I am still quite introverted, but no one except my wife really knows that. I understand that people aren't rejecting me, it's just the way they are or they're having a bad day or want to be left alone. It's not all about me.
And by extension, it's not all about you. Accept your lack of importance to the universe and life becomes easier to live in.
Make sure to take a few hours learning dancing from someone who's really good at it, or go to some sort of dance class, and pick the right club for your dance.
In my experience, your appearance only matters for the first 3 seconds of meeting someone, after that it's all down to your personality.
Remember: everyone is attractive to someone. The point of mentioning women buying me drinks wasn't to brag, it was to point out that as you become more at-ease and confident, it shows.
There is also Dale Carnegie's 'How to win friends and influence people' https://en.wikipedia.org/wiki/How_to_Win_Friends_and_Influen...
Apart from that, maybe join some kind of regular group that is more oriented for social than physical? Toastmasters or something like that or even board game groups (most games have some social aspects to them). Wine tastings also come to mind. Just choose activities where you know you will have to speak with people.
You have Aspergers?
Have you considered any improv humor stuff, where un-planned-ness is almost the goal?
He's got some great videos like how to warm up to conversations
https://www.youtube.com/watch?v=AtZUx6VLoY0
His stuff was so helpful to me I went to a seminar and then hired him and my social skills went through the roof. I got better clients (I run a consulting company), my marriage improved, and I just feel all the more outgoing despite a lifetime of being introverted.
* Read How to Win Friends and Influence People
* Read The 7 Habits of Highly Effective People
* Join Toastmasters (and, importantly, participate!)
* Make it a part of your life to continually study psychology and human nature
My life has also improved personally/professionally/socially since I got fired from my last job in 2013 and went freelance. Having to run my own business has forced me to develop social skills and freelancing has given me the opportunity to regularly change the group of people with whom I'm surrounded, which has allowed me to "collect" people I like along the way, which can happen at a regular job but much more slowly.
Read How to Win Friends and Influence People
This is a book that very much should not be judged by its cover.
Assuming you work in technology, you really know and work with middle aged people who are not aware of the terms selfie and Twitter?
As part of a PIP* I got assigned to Toastmasters. I have no use for that since I already know how to tell stories, but... that's what they do.
If you have nieces, nephews, read to them. That's how I learned it.
oh yeah it ended ... like that why do you ask.
And please understand that I am probably risking my immortal soul by saying this. But life is more fun when you can tell stories. It's the* basic fundamental thing of human cognition.
For me social dancing ended up being great, even though I never would have thought of myself as a dancer.