You know, it's fine to ask questions. Some may seem too personal to ask on a first date. Hey, I never really tried dating. Actually, I've never dated at all, not in the traditional sense. I've hung out with some persons of interest before. These encounters were interesting. Hardly any of them went anywhere soon afterwards.
You can get a sense fairly quickly if there's no future in a relationship. At least, that's what I've come to believe. In my teenage years, though, I was pretty delusional. Weren't most of us? Very few of us knew what we wanted in a partner. Our teenage years mostly teach us what we don't want. That's actually probably more important at that point.
Hormones do some funny things. This isn't to say those I found attractive in my younger years really weren't. They were, at least physically. Just not in the way that matters. The only thing that matters is personality. And yet somewhere along the line you end up convinced that you have a type. Let me tell you: there isn't really a type. You just happen to meet someone and it works. No matter your differences, you just make it work.
The secret? Just do your thing. Get that picture of the perfect soul mate out of your head. But don't settle. It's OK to be shy. The right one will be interested. Just don't miss your chance. I followed this line of thinking. It worked for me.