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Well. I'm the usual "Nice Guy", except that I don't really fit into the same criteria that most people seem to hate about "Nice Guys" (ie, "Nice Guys" hate anyone that is in a relationship, Romantic delusions, etc). I know I'm the one with the problem.
I also came to the realization that, technically, I don't have an actual personality. I talk with friends freely about interests and hobbies, but when it comes to conversing with acquaintances and people I generally don't know enough about, I freeze up. I'm a blank tape. Considering how, you know, normal people talk freely, it's like I have an extreme case of social anxiety. I get nervous, tense, jittery, and invoke a mild stutter when talking.
I was really quiet when I was in Elementary school. The kid that got picked on, etc. In High School, the exact opposite experience; talked with people freely, and I was socially accepted. But members of the opposite sex, no go there.
Now, I still tend to be relatively quiet with acquaintances and general people out there. I just tried talking to this girl [I have a thing for] where I work, and needless to say, I'm pretty sure I creeped her the fuck out without realizing it (Used to talk to me, Doesn't anymore. And the "Hey"s and "Hi" are have an added unspoken "Now go away" layer added to them"). When it comes to "Flirting" or "Chit Chatting" with me, imagine Chris Farley's explanation in the movie Tommy Boy, when he's talking to the waitress in the restaurant about his failed attempts at selling Callahan Brake Pads. Yeah. Friends give the usual "You have to act like an asshole", but I can't even begin to attempt to do that, if I get socially anxious the instant I talk with an acquaintance.
So I don't really know where I stand here. I want to fix this, but the usual "Talk with more people" ends with the same social anxiety, and me cutting my losses and aborting as fast as possible.