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Originally Posted by Akathriel 
Patrick have you ever been diagnosed with Aspergers lol?
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Ye that was the first thing that came across my mind too... and I know something about aspergers, I'm slightly autistic myself. Used to be kinda freaky too but in the last 3 years I've learned alot about social interaction and I have no problems what so ever when talking to a girl now.
1 tip though, it doesn't matter who starts first but always try and have a point in the conversation where you show interest in her and what she's talking about. On the other hand, don't be to nice, a simple, funny sexist quote or whatever, else they'll easily think you're a wuss

But don't try these tips in the beginning, if you really are an asperger, they'll sound weird. Go out more do some stuff, etc and get used to having more social interaction.