I have read all of Plan9's posts on this thread that are "lessons" etc. and have loved every one of them. Although I haven't applied any of techniques, this thread has inspired me, because now I know there is hope for me!

. I have used some of the advice in general with girls I know, and it works so well. I am not getting any from them but I keep their attention for much longer.
First a little about myself: I am 5'9" and 270 lbs.! I have pretty much been fat all my life and so getting in shape, working out, etc. were just completely foreign to me until about a year ago when I tried (unsuccessfully) to lose weight. So needless to say, I just don't have much confidence when it comes to girls. I am a guy who likes to joke around a lot. I am the type of guy who can make people laugh with just a little twist of my face or one word. Most people would describe me as goofy.
My serious problem is always becoming friends with girls that I am attracted to. It ALWAYS happens. I am a "nice guy" and have been taught to respect women from a very early age. I see guys doing the stuff described in this thread and think, why the hell are girls going for this stuff. I guess I really just didn't want to be another one of "those" guys. Of course I end becoming another friend.
My girl to guy friend ratio is about 10:1, which probably says a lot. The problem is that I just don't like hanging out with guys. I am really interested in stuff like classical music and art. Most guys don't want to go to concerts and stuff.
So here is my question.
There is a girl in one of my classes who is really smart and a girl who studies a lot. She basically DOESNT date. I thought she was really boring until I got to know her a little better. She actually is pretty attractive though, and lately I have been trying to knock down her no dating walls. I am good friends with her roommate and she basically told me that "she just doesn't think of guys that way". But here is the thing: I think I can, with the right approach, get her interested.
This is the type of girl I usually go for. Maybe I am just getting myself into a corner, but I just don't find the dolled up girls attractive. There is way more I could post.
So how do you get those girls who are really smart and make it a point not to date?
I know deep down she wants someone, but I just need to make her see that.
Edit: My last girlfriend was similar, but I think that all happened by accident and by me being insanely persistant.
Edit: She isn't gay.