The answer to your question is to buy the book "How to Win Friends and Influence People." This was written by Dale Carnegie, probably before your parents were born, but it has remained firm favorite for decades because it WORKS!!!! There is no better book on how to relate to other people and it helps you understand how to get the responses you want when in a social situation. Mr Amazon.com has copies right now for about $15, so all you have to do now is read and understand the principles and your shyness and awkwardness will be ancient memories.... I cannot recommend it too highly - it transformed my life and that of my two daughters - as it can for you and your destiny. lol....
Say hi to everyone honestly, prepare yourself-think before speaking. Be around people whom you are confortable with. Try different cloth more often, even colors you dont like, just be different-less shy. Be good in a sport or hobby, practice it, let others know, so show off a bit-less shy on what you do.
Are you sure you're not an introvert? All these years I thought I was shy but it just turns out I'm just an introvert with social phobia (and arachnaphobia, but that's not important). They say to get over a fear is to dive into it, now diving into a pile of people sure won't help but practice conversations and speech with people you know and STEADILY expand from them- talk to people you don't normally talk to, meet someone new. That's what I try to do, still working on it, but I've gained many great friends since middle school because of trying this.
Do something weird or make friends with silly people :3 Once me and a couple friends were hugging a statue in our school in the middle of lunch while screaming " HE'S MINE!!! " " NO HE'S MINE!!! " And yelling out " PENIS!!! " :3 Good times, good times... Point is, I think if you're around silly people, you'll feel less shy about being silly yourself.