So for what its worth I only started to figure myself out in my 30s and I think the goal of being comfortable in your own skin is a worthwhile one.
The coolest people are able to be themselves without being worried how people feel about it. Its cool to not worry if people think you are cool. Its cool to treat everyone with respect. Its cool to be yourself even if its kinda weird (unless its like socially unacceptable, obviously).
I guess when it comes to other people…we only have to like some part of other people…like the things we have in common and/or the common endeavor we are working on.
George Harrison was the quiet Beatle and he was the coolest one (my opinion). Just be you man.
As for social skills, its like woodworking or anything else…something people might be naturals at it and others like us have to work hard at it. You will get better with it in time and I have found that having a positive attitude (or just acting like it) is helpful. I have also found that people pretty much universally love compliments and I generally limit it to something they have chosen (hair style, shoes, nails, etc) and not like, their eyes or their looks etc…but maybe that is only because I lack the confidence, but I don’t want to act like a creep.
If nothing else metal my goals have been to act like a person I would think is cool and would respect if I met them and then I would kinda be that person (…if that makes sense). If I act like someone I would like…its easier to like myself. As for meeting women, I think if you are positive and confidant/comfortable as well as “not too eager” I think that is pretty much 90% of what makes a person attractive.
The short version is take it easy man. The person you are is already cool.