I got coffee with a girl once after talking about some sign posted about religion on campus. She had a boyfriend, so the convo ended up being more about brainy stuff and personal beliefs than just a fun shoot-the-shits. In the middle of talking to me, she said, "I feel like I'm at a job interview."
This is a huge problem for me. I like being really straightforward, I like serious and academic conversations and debates. I like learning about people's histories and what makes them tick. But none of that is applicable in any way to pickup or even just good beginning conversations. It just doesn't go that way.
I know this. I don't do it all the time. But I still keep reverting to it when I'm nervous or running dry on things to say because it's easy and familiar.
The same goes for being overly polite and platonically/formally conversational. Another poster here told me for simply not holding my frame on a joke that I'm a yes-man, that I agree too much with what women say, too polite and too straightforward, too boring.
Maybe he's right, but is that something that can be cured? I'm not always like this - I'm a completely different person when I drink and I'm in good state, but otherwise trying to meet new girls and people is like pulling teeth for everyone involved. It's not right.
My last sticking point is that I am terrible at coming up with things to say unless the other person initiates. I'm a rockstar at coming up with stuff that relates to what others say, but most of my conversation starters are usually some form of "x thing in the background reminds me of y thought," or even just "random thought," hoping that they'll find some way to relate. I don't really know what good open-ended questions are, either, because they come off too interview-ish or aren't actually questions that tell me something I'd really want to know about the other person.
Has anyone else had these problems, and what did you do about them if so?
(If it helps, I'm pretty much culturally illiterate. I don't listen to most music, I rarely watch any movies or TV, I don't have any interest in or knowledge of sports, and I spent several years of my life in online gaming. I'm just being brutally honest here so I learn what I need to do to compensate.)