I was like that. Actually, I'm worse. I never got laid before I was 32. I've always been very respectful of boundaries, didn't want to impose, and due to social awkwardness, that meant I had a hard time approaching women. And to be honest, I don't really have an easy solution; in the end I met my wife and we've been happily married for 12 years now.<p>For a while I did give up. Particularly in university, I wasn't very interested in the dating game. I did have the occasional crush, didn't know how to act on it, and when I did, it generally amounted to nothing. After 30, I decided to try this online dating, went on lots of dates, most of them amounted to nothing, then I met a woman I fell madly in love with, and she apparently with me, but we soon realised it wasn't going to work: she smoked, I hated smoking. I wanted children, she didn't. We broke up, and I soon met my wife on that same site. And I believe she was the one to contact me first, which definitely helps.<p>That site that got me two hits in a row, wasn't a normal commercial dating site, though. It was really cheap, low threshold, aimed specifically at Christians, and not just at dating, but also at friendship. And it supported blogging. Maybe that lowered the threshold somehow. I don't know. But I've become a strong believer in non-commercial, focused on special interest, dating-but-also-friendship sites.<p>For one thing, commercial dating sites are mostly scams. OKCupid used to love exposing those scams, but I believe they've been bought by the biggest dating scammer, so they're likely as useless as the others now.<p>Ultimately, all you really need, is a way to meet new people with similar interests to yours. Not identical, but it helps to have some common interest, whether it's a hobby, religion, activism, or whatever. It doesn't have to be a dating site, it can be a real-life activity. It can be an online game (I know a couple that met on World of Warcraft). Make sure you can talk about something other than dating. See if you can talk to them about other stuff than dating. If it turns out you can talk to each other, ask her out for a coffee or some other small thing. Or maybe do something hobby related together, see how that works out. I suppose you've got to become more confident at making the first move if you don't want to be totally dependent on the whims of the other, but the move doesn't have to be aimed straight at dating.<p>Though to be honest, I don't know how much my advice is worth. People like me never get a lot of dating experience; once we find the right person, we stick with them.