I can relate. I went through puberty very late (15 before I even had a wet dream); and watched the whole junior high dating scene like an observer from Mars. I discovered drinking at 13 and distracted myself with that until I was about 17. I did go to dances and kissed a few girls, all one shots with no second or follow up date. I spend a lot of time in the proverbial friend box. At 17, I actually filled out pretty well and grew into my skin. Figured what the heck and just started asking girls out while a bit buzzed. I lost my virginity in a drunken one night stand, but for the most part, I was no sex animal and had no clue what to do. I did date a lot and was quite popular with girls but I really was insecure about my sex prowess because I figured everyone else was so advanced and far ahead of me. At 18 I quit drinking and lost the nerve to approach girls cold sober, all that old rejection fear came back, so I just stayed with an evil shrew of a girlfriend who I met pretty drunk initially, but college and professional school were filled with missed opportunities and times I was just so afraid to take that risk to close the deal with anyone else. I married the shrew very young. Many of those occasions still haunt me today because the marriage was pretty dismal. I just think of all the great girls I passed over because I was so chicken sh*t that I just stayed with someone because I was afraid to be alone and have to face the dating world sober.
Here is my advice for what it is worth. Start working out regularly at a gym with lots of girls. Take aerobics or yoga classes, the female-male ratio is 20-1. Talk to as many girls as you can about yoga, the class, or the instructor. At some point, ask one of them to go for coffee or something very no-pressure. Say right away, I'm not trying to pick you up, but I would love to have a cup of coffee and pick your brain about something. This first girl should be someone you have no interest in having a physical relationship with. After you've talked about yoga or aerobics, tell her about your problem and explain that you are taking the class to gain confidence, lose weight, and learn to approach girls for conversation, and ultimately for dating--and to get in shape and learn yoga. Tell her that you are not trying to pick her up but would love her her advice about meeting other single people and how she likes to be approached. Tell her that you want her to be honest with you because otherwise you won't learn and change your patterns. Tell her that you know she is out of your league and that you really are just trying to figure everything out after years of fear. (See you are doing research here). Then stay friends with her in the class and don't ask her out, unless she approaches you to go out again. Tell her that you are going to try and have similar conversations with at least 3-5 other girls in the class so you can learn how to relate. She might tell you others to talk to in the class. Stay friends with all of them. Repeat 3-5 times with other girls in the class until you become very comfortable and have learned something about what they like and don't like. Again, the point is to see women as human beings that have the same fears, desires, wants that you do. Learn to talk with them and find out what they look for in romantic partners.
Once you've done that for a month, then we will talk about stage 2. I would be very surprised if at least one of the 5 does not offer to fix you up with a friend in the meantime; or invites you somewhere herself. Again, you have to walk before you run. The goal is to go on a real date.