Okay, they say take advice with a grain of salt, but I do this and it works, I swear! Like you, I was VERY shy before, would not be able to utter a word around women... until I started watching the Late Late Show with Craig Ferguson and seeing how Craig interviews beautiful young actresses. Go to Youtube and under search, type in malinky2stoatir. You'll bring up this user's profile who uploads all the Craig Ferguson shows broken up into segments. Now try to find an interview of Craig talking to some of the following:
Kristen Bell
Amy Smart
Emily Deschanel
Dr. Kara Cooney
Watch how he talks to them, makes fun of them, makes fun of himself and watch how he keeps them laughing. This is what you want to do (even if you don't have a foreign accent). It'll take a little practice but ask questions and play off their answers in a light humourous way. Remember, you want to go for "charming" not "creepy." Anyway, I've been doing this at work (we hire lots of attractive young women in my building) and it works, because a lot of them will continue to pop by my office during the day to chat and I'll just flip into "Craig mode" and keep them laughing. In the long run, you'll start to learn lots about this girl because you're continually asking her questions and finding out about her; also you'll build your conversation skills so when you do ask her out, you won't have those awkward silences during your date because you don't know what to say. See if that works!
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oh my I am in the same position as you! I have no idea how to start a convo...i personally feel that guys should be dominant and make the move, and I myself would love it if my crush came over to me and just started talking about anything, and I can laugh along and join in, the fact that he's shy and nervous is making me even more nervous...i kinda need my man to be dominant and take the lead, because I'm a shy person, so yea I recommend you walk up to her find some dumb excuse to talk to her, ask her for a pen to borrow, crack a joke about a teacher, anything I'm sure she will be relieved and will join in and give you her #
Maybe ask her if she likes you or what... If that's too hard, then maybe get someone else to ask her. Or just try to extend your conversations a bit. I don't know...
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