I think I might have experienced a small miracle today; suffice to say that things turned out for the better.

Chatted in length with an old friend from high school, and he provided the brutal honesty I needed to hear:

( LOOOOONG Bro talk about Girls, Relationships, and Whats My Problem? )

We then talked about how I didn't want attract a girl just because I may make a lot of money in the future, comparing that to beating a game with cheats on; hollow. Then I asked for specific guidelines on how to approach girls and what factors to consider when deciding to ask a girl who you've befriended out. How TV shows and a common like for anime are insufficient, and how common interactive interests are necessary... like Tennis.

Now that I've had my refresher course its up to me to execute.