30s/m here. ADD, anxiety, depression, dysfunctional parents, probable sexual abuse as well. Brought up traveling a lot, never felt comfortable or right with any social group, was hard to understand where people were coming from. Different languages, cultures, etc. Felt out of place and laughed at a lot. Spent my mid teens in an all boys boarding school. Back in 'regular' schools afterwards, sex just wasn't something I understood people had. Happy healthy relationships didn't really compute. Spent a lot of time hanging out with people who weren't really my type but I didn't know what else to do and they liked my company. Most of the girls weren't into me or I wasn't into them or I missed the signs. I would try to relate my interactions to characters and people I had seen and tried to mimic them but it never lasted or worked too well. Even work was too taxing to keep up so I felt too useless and undesirable to try. Never really did college or activity groups so work and friends were my only outlets. I did meet an occasional girl who liked me up until I revealed too much and/or emotionally fell apart on them before anything had really happened. That happened repeatedly. A lot of girls I liked were too young to relate where I was coming from but older girls intimidated me and were less attractive. Sometimes I would confess my feelings to lady friends and friends of friends and just make everything awkward. Sometimes the good friends I liked a lot would sleep with my friends but not me. At one point my friends' in a band were all dating girls I was into first. It hurt a lot, a lot of the time. I had great porn though and that didn't require me to relate to anyone, so I'd fap to that sometimes for hours a day. Went on occasional dates with girls I never talked to again. Made out with an occasional non-date that didn't last. Wasn't until I moved to a new city, had a steady job and started an OKCupid profile with sex as the intention, specifically omitting a lot of the lack-of-sex and antisocial shit I wanted to say and found a lot of high matches with polyamorous girls. Went on three separate dates and found an awesome girl on the third try who had a lot in common. She was a few years older, not as thin as I would have liked but she was pretty and cool and that was enough. Third date or so, after many drinks, I finally made the move from across the table to sit next to her, we kissed, went back to her place, and screwed. Afterwards I asked her if she'd believe it was my first time and she laughed and said don't lie. I told her why would I lie, it's embarrassing. We laughed and were together for 6 months or so, until I got depressed again, sex became repulsive, and I stopped wanting to be around people. It didn't solve my problems but I guess I'm glad I got it out of the way.