I started working at a local radio station in the small town where I was living at the age of 16. Once I got over the terror of the mic fright and became comfortable doing the job, I started getting flirty with the girls who called in on the request line. Since I didn't have to actually see them, it was easier to relax and they were impressed with the job which, to them made me seem like a sort-of celebrity. After awhile I started going to meet some of the regular callers, dated a few, lost my cherry to one of them (at eighteen) in a moment that was awkward, embarrassing and disappointing for us both, but as soon as it was done we didn't have much time to bumble and feel stupid because her Dad came home and I exited in comedy-movie fashion, trying to step into my pants as I ran for the door. She wasn't allowed to see me anymore after that.
Then my family moved and I started working in a slightly larger market. The girl I really learned things properly from was a young single Mom known to the other DJs at the station as a notorious 'groupie' - who collected DJs as souvenirs. She invited me over, literally grabbed me by the junk and led me to the bedroom. From that point on, I quit worrying that no one was ever going to want me - I was still awkward and socially uncomfortable, but I figured there were at least some girls out there who would like me for who I was. Turned out there were a lot who did. It just took for me to stop being an Eeyore about it.
Once I had a little faith in myself, things just seemed to work themselves out. I was never as smooth as a lot of guys, but it didn't keep me from making a connection every once in a while. Looking back, it happened a lot more frequently than it seemed at the time. Back then if I went three months, it seemed like an unbearable dry spell.