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I think part of it has to do with me thinking too much about what to say, instead of just letting it flow. For instance I met this very attractive girl at a bar and we had a great conversation. I got her number and before I left kept saying how we should hang out sometime. She says, "you have my number, you know what to do." I call the next day no answer...Even leave a text and get no reply. Similar situations have happened like this before where I get the number and nothing happens after that.
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