GabrielDuquette comments on Mitigating Social Awkwardness - Less Wrong
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I'd add: cultivate an awareness of social dead ends/necessary evils. Determine when you can revel in your idiosyncrasies without consequence -- even to the point that you're deliberately putting people off or weirding them out for your own amusement. Doing this judiciously will release some of the pressure you're probably feeling when you interact with someone you really want to know.
I like the way you think!