You like totally described me.
I feel the same way, I was sort of a loner in high school. I mean I had a set of group of friends that we would hang out, chill, but that was because I wanted to fit in, not because I was compelled to do so. It was more out of necessity.
I played a lot of Warcraft 3, and gaming in high school, and while I went semi-pro,l I think that is what has led to my inability to connect emotionally with people. I learned some nuances, but most conversations relatively turn awkward, or I sometimes don't have the right way to express or convey what some people can do fluidly.
I think you just need to find the right group of people. Fitness usually has a wide array of people who are always looking to find other work out buddies. I also think yoga is a perfect way to meet women.
From self help books and materials I've read/girlchases articles by Chase, I believe you must have 6 qualities.
1) Have a thick skin, and caring less about what people think of you. The statement itself is contradictory, because social proof and social norms dictate that you must have a strong sense of knowing yourself, and you should care what people see you as. Just don't let the negativity affect or cloud your thinking. I have a penchant for doing this a lot, so I always tell myself to remain positive.
2) Find some way to break free from stress. I mediate now. I also do some yoga, and when I was younger, I used to breakdance, (bboy.) I'm pretty sure fitness or working out can be the same exact methodology!
3) Patience.
4) Be warm to others, express gratitude, and empathy. You don't have to be a push over or Mr. Nice-Guy, but when other people see how you treat others, it will reflect on how they view their perception of you.
5) Humor.
6) If your passion is getting with girls, then I believe you need to make friends with a lot of girls. I was never good at connecting with guys at high school, but I was always good at being friends with girls, who would then hook me up with their friends or try to match make.
___
What is your main purpose or goal when you talk to someone? Is it to be friends or lovers?