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I had a BAD problem of this through my High School years. I couldn't ever go up and talk to a girl, I never knew what to say, and I was sure she wouldn't like me.
Honestly, I got over it by learning how to dance. We were in Texas in a small town, so the only thing to do on the weekends was to go to this dance hall (where any small town High Schooler drove +30miles to go to). I learned to dance, and all I had to do to talk to the girl was ask her to dance with me. In the 1on1 time on the floor, it was obvious this girl was just as shy and doubting as I was. After 20 approaches, I was shot down maybe 4-5 times.... pretty good ratio. Each one helped build my confidence.
Every once in a while I'll be hit by a girl so beautiful I'll be stopped in my tracks, and I still get shot down on occasion, however it's far and away easier than I ever had it before.
Keep the conversation light, ask her questions about her, let her talk as little as possible, and throw in some jokes based on what the conversation's about. You won't hit it off with everyone, but you won't pine after them like you and this rockabilly chick weeks/months afterwards if you don't.
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"Smite the rocks with the rod of knowledge, and fountains of unstinted wealth will gush forth." - Ashbel Smith as he laid the first cornerstone of the University of Texas
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