Many people will tell you that shy could mean just about anything...and there's a different answer for each situation. My personal experience is that MOST guys feel some kind of shyness or nervousness at least SOMETIMES with women. The key is to get yourself into the situations and LEARN HOW TO DEAL WITH EACH ONE.
Experience builds confidence and confidence creates action which leads to more experience. Just get out there and start making friends with women. Get online and start chatting if you're nervous about doing it in person. Keep working on it and taking steps until you can talk to anyone anywhere.
You wouldn't believe how many other guys are dealing with a similar situation... If I were you, I would stop beating myself up over this, and just start doing thethings that will make her feel more attracted to you. It's important to treat yourself well.
Instead of asking "Why am I so shy?" and such, commit yourself to doing something each day and getting better and better; keep working on this and improving.
It is important to realize when you are TRYING to impress and show off to women as this will ultimatley be your greatest downfall. This is where you're going to freeze up as a result of trying to force something you're doing naturally. I personally can talk about stupid anything. One example I can give is starting a conversation about something as abstract as my legs being tired from exercising on Wii Fit and we will go off on random threads such as how often we exercise, being rambunctions and high energy, liking to keep fit, ect.
I can remember the akward silences and the girls favorite phrase being, "well talk to you later." I can remember all of this perfectly so don't ever feel bad about it. Interestesting conversation is FAR easier than you think but they key is to NEVER force it or else you're going to draw blanks. Like anything else the best working things are the most natural.
- Chris 
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). I know like 1/4 of my highschool (theirs like 2,000 kids here). The only problem is i cant find a way too hook up with any HBs because they are always in groups and alot of them are shy as well when i try to talk to them..I can start a easy conversation with someone but cant find anyway to continue them... What do i do?
