Let's Get Real said:
You and I are very similar. Did you get good at poker and everything else because there is a love there or is the love only generated from proving that you can do it and from the results of success?
I only wanted a girlfriend to prove that I could be loved by a pretty woman. It meant to me that I was a success. How is your relationship with your parents?
In response to your points:
1) I got good at poker because I wanted to make money, haha. Nah, you have a point: whilst I enjoy getting good at activities because I enjoy the activity itself, there is also a degree to which I get off on "success" more generally and the results of success. Most people who I know that are good at something are like this, I think.
2) I certainly don't ONLY want a gf to prove that I could be loved by a pretty woman. Firstly, I'm not even sure I want a gf at this stage- dating around and messing around with other people's "gfs" has opened my eyes to just how unsuitable most girls my age are to committed relationships. At the moment I just want to lose my virginity and have a bit of fun.
As I said in the OP, one of the reasons I was confused on Monday night was that I view myself as highly successful, and yet have trouble with girls. That is to say, in no way does my having a gf or not determine whether or not I view myself as a success. I just sometimes find it frustrating that I can do so many other things that most people can't and yet very "average" people have sex lives and I don't.
3) My relationship with my father is very very good. Okay, he's a classic beta male and in that sense a fairly poor masculine role model, but he's there for me and provides advice whenever I need him. I would trust him and value his judgement on just about every issue except girls.
My relationship with my mother is somewhat more rocky. She is by far and away the dominant force in my childhood home; her control over my father is so complete that I'm not sure he even notices this anymore. We are both extremely dominant personalities who like doing things our way, which inevitably leads to the occasional argument. When she's not emotionally charged with stress from work/ anything else, my mum can be a great sanding board for ideas. However, this is more the exception than the rule- most of the time she is fairly embittered and pessimistic.
Why do you ask?