Hmmm, just now noticed this thread...
Here's an idea that didn't come up in the other Posts: get into the arts more. My school years were miserable up until the end of my junior year (11th grade). Starting then, I picked up playing guitar (Note, chicks dig: guitarists, scars, guys who can/do cook/clean, guys who listen
). After that, I started leaving the house more, doing things. After that, I went to a summer program in Information Technology that was offered by Pennsylvania's Dept. of Education (I lived in PA then).
Senior year (12th grade), I kept playing guitar, took an art class (sure, I was in a class with all the freshmen, but a friend and I decided we focused too much on academics and we took it together), and just felt a lot better. I also joined the school's tennis team... which was only possible because there was just barely enough interest to keep the program alive, and the team was perpetually in the cellar for the rankings. But, I met people from other schools, and had a good time, even while losing. In fact, to this day I have yet to win a tennis match
As for the situation with your female friend, I don't really have any advice to offer, as I'm still working on figuring that out myself. Tried asking a girl out once, and was given a resounding "NO" in a fashion that was quite harsh... never tried again since. I'm just sticking with meeting new people until I find one who I think is worth it.
I hope all this helps you find a solution to your troubles.