I'm a lesbian, so I can't speak from a male perspective, but I've always been super socially inept and also really find it hard to become infatuated with someone. It's my biggest downfall with other people.

I met my first girlfriend when I was 19 and in college, she just seemed to overlook all my obvious flaws and found my shyness endearing. She was super extroverted, I'm the total opposite. But I thought she was cute and we made plans to hang and that was that. If you just put forth even a little effort to the person you've got your eye on, they'll either turn out to be someone you can be with or not. Sometimes it works, a lot of times it might not just because it's not right. And sometimes an odd pairing is a surprisingly great one. We broke up ages ago (getting older and figuring our own shit out), but she's still one of my best friends in the world.

Just leap! Or even hop. I thought I'd be alone forever too, but I quickly realized I'd just been talking myself out of trying so I wouldn't be disappointed.