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Shyness affects men both unattractive and handsome. I remember David DeAngelo once saying he's coached men who looked like male models who were terrified of approaching a woman.
Practicing is the way to go. Start by going to a clothing store and asking the female working there to help you find a shirt/pants/whatever that will compliment your body. She's there to help you. She'll talk to you. Seriously - keep doing things like this and it will get easier. Once you feel comfortable with that, ask a random woman the time. Or while at the grocery store, when you see a woman picking up a box of something, ask her if it's any good. She's going to be friendly. I promise she won't throw the box at your head and call you named. It will get easier.
^ This is good solid advice. It all starts with that first tiny step, which leads to the next. Next thing you know, you LOVE speaking with women and getting to know them.