When I was young, I think I shared some of your situation. I'm 44 now and have worked through some of the self-esteem issues. However, I felt a lot like you when I was thinking of asking women/girls out. I didn't date in high school - I was youngest in my class (grad. at 16), didn't get into social situations. I was introduced to my first girlfriend and it went great for a few years. But if I wanted to meet a girl - I was scared and held myself back. It really boiled down to how I was raised. My mom and I were it - and I was adopted. So, I think I was "shy" as a kid (now, we know that shyness is really self-esteem issues and other anxieties). I always felt that the girl would reject me or not be my type or not like what I like to do, etc. so, you may feel similar.

What I think you would want to do is just "get to know her". Forget looks - just ignore her body. Just go for her mind. "Hi - I'd like to learn who you are as a person." That kind of thing. If you set it up so that you're mind is talking to her mind, you can get over the "typical" stuff of dating that tends to be a big distraction. It's like stage-fright. But most stage fright goes away once you're on a stage. So, take the butterflies in your stomach out with you - and let them fly away at the door when you pick her up. Talk, don't flirt. Ask her questions but also share yourself too. Who cares if the bands you like are not her favorite - or your hobbies seem a little goofy. Who knows - maybe she'll enjoy those parts. If not, then don't punish yourself - every couple has a lot of differences, maybe more differences than similarities.

Best part of dating is sharing what you know "truthfully". definitely don't lie. don't say your dad is the owner of some great company - tell the truth. The old saying is "telling the truth means you have far less to remember." Works out well.