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Clay, what you need is a reliable wingman. Someone to talk strategy with, get input, help with icebreaker maybe even help with a quick getaway if needed. Everybody has at least one friend that is the smoothest mother****er around and can pull almost any ass he wants... or a chick friend that will introduce you to random stranger chicks she thinks are hot. Ice breaking is what seems to be your problem... for whatever reason; fear of rejection, former fattiness, you meet them on the net cause you have more experience with internet conversation. You need icebreakers. You are clever, so once the ice is broken, you should do ok... I had an Army buddy that was just like you. I would always go talk to girls for him or drag them over to him and put him on the spot. Eventually his confidence came up, and he was a true poonhound.
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