I'm not an otaku or "socially awkward" myself, but I can't imagine dating an otaku, much less one I met at a con.
I'm not sure why, but I think I'd find it creepy more than anything. Maybe because to me, watching anime is a hobby, not a lifestyle, but most otaku seem to take anime way too seriously. Heh...
My boyfriend barely has any idea what anime even is (though he does lurk 4chan). I think if he was an otaku, our relationship would be really strange. I have otaku friends who date other otaku, and their relationships always end up turning into "I'm a bigger nerd than you"/"My anime are