I will say up front I am a 38 year old virgin.
From the age of 7 to 16 during school and college I had very little in the way of friends. I was bullied constantly and I was suicidal at 16.
After finishing school, I decided to concentrate on ME and my self-improvement. I decided that life would be worth living but I knew it would take a long time sort myself out. So when it came to going to college I made the very conscious and deliberate decision not have friends because I couldn't trust anyone and I stopped associating myself with the kids who I was at secondary school with (because some of them went to the same college).
When I finished college and went to university I was chronically shy. This was 1994. In my second year of university I ended up sharing a house with some guys who I am still friends with and we chat once a week, almost twenty years later. In the late 90s, I started working in a supermarket and I am still in regular contact with some friends I met through that.
But when it came to socialising with strangers or going somewhere and meeting a group of individuals I had not met before was difficult but I was up for the challenge because I felt I was comfortable to do it but that has only been in the last 6 months.
I said that my self-improvement started at 16 and I feel it is only now that I am beginning to feel comfortable in my own skin. Up until now, the relationship side hasn't really bugged me too much (say compared to ten year ago) and I feel more comfortable now with the idea that I've never had a girlfriend than I've ever done before. I am saying I am happy single.
What I suggest you do is go to
http://www.meetup.com and join a local group. It doesnt matter the age group. You just need to get yourself out of your comfort zone. As you get more used to expanding your zone, you can push your boundaries a bit more.
Life can be crazy sometimes but it is what you make it so the best advice I can suggest is: JUST BE YOU. Don't feel you need to live up to other people's or society's expectations.