PS- You have been warned.
But yes, it's like Montez says- it's a matter of confidence.
But it's also an age thing, and that's something to be careful of. The older you get and the more confident you get, the more you come to appreciate women as just being people with more enjoyable sex organs. No reason to be intimidated by them, or feel devestated should they ruin your ego. They're probably as screwed up as you are.
But confidence matters, and part of that has to do with being comfortable with yourself and liking yourself. (Get your hand out of your pants Morgh, we all know what you like to paint a clown face on).
But there something about age that matters too. A lot of you guys are young so it makes sense that you have self-confidence issues and are shy. If you muscle up the courage to ask out a girl you like and she rejects you, it's a ego blow and sometimes it's hard to overcome that. The older you get, the more causal become your relationships with women, the more easier it is to form meaningful connections.
But back to that age thing- be aware that girls are going through their own issues as well. Just as a lot of you younger guys are getting issues of self-confidence, a lot of younger girls are figuring out who they are, what their sexuality means. That leads to a mess of emotions and some hurt feelings.
Accept that women are trying to get their shit together just as you are. So it's easy to get hurt when you are in high school or in college, or if one of the two are playing headgames or cheats or ends the relationship for stupid reasons.
This lasts, in my opinion, well through college. After college girls are often attached or bitter about something serious that didn't work out. But as girls get older they get more casual and more fun because they figure themselves out. Which is cool, because the guys are usually getting their shit together at about the same time.
In my opinion, the best dating years start after college, probably between 24-30. At that age they are usually past being girls and well on the way to being mature women. When I was 25 I was dating a girl that was 21, and swore never again. It's the age thing.
But you see, when you're thinking about girls you're usually thinking about how you see things, how you feel and it doesn't make much sense that they don't understand. Well the same goes for the girls. So be a little forgiving of each other and take it casual.
That last bit advice is, in my opinion, the wisest course. Don't take the first six months of a relationship too seriously. Have fun with it, enjoy it, get to know the person, and be yourself. If it doesn't work out, well, ok. It was fun while it lasted. If after six months, check it again and take stock of your relationship. Are you emotionally tight?
Honestly really matters. A good relationship is kind of like getting naked emotionally. Being yourself and being appreciated for that. That's the risk in a relationship- that the person you're with won't appreciate you for what you are about. But that's what a good relationship gives you- the freedom to be yourself, honestly, with someone you really value and to appreciate a person for who they really are.