Regarding social skills, I feel like I can relate to how you describe your situation. I was extremely socially anxious when I was younger and basically avoided any social interactions I could. Throughout highschool and college I never had any friends to speak of or dated. I mostly shut myself away with video games and other solitary interests.

I moved to a new city away from my family when I was 27 and that was when I finally pushed myself to start changing things as the loneliness really hit me. I started going to meetup events and work lunches with people. I started reading up on social skills and trying my hand at dating. Roughly 5 years since then I've actually done pretty well for myself, made some good friends, had some good experiences with dating, and I'm rather happy with how things have shaped out. I'm still kind of awkward socially but gotten more comfortable with putting myself out there anyway and found that a lot of people don't really mind.