Ok, so...
1.) Like what's already been said... stop being his lackey. >.>;; I can tell you right now, being at the grand old age of 23 that Highschool doesn't matter. If you make some really good friends, you'll keep them, but other than that, it's weird to be friends with someone more than 5 years after you've met. Anyway, have you got any kids you consider friends? Why don't you ask them to go do things with you? Once you've asked someone to hang with you, and you go to some arcade* or to the park to play soccer or something, then they'll probably ask you to do things too. It's a Quid Pro Quo situation, really. I moved around a lot when I was a kid, and I went to two different High Schools. I've kept friends with both, and got invited to do all kinds of things because I invited people to do stuff too. After the second or third 'cool kid' party I went to... I decided that the Scene was Completely and Utterly B O R I N G. I quit going because I wasn't into beer kegs and excuses to sex up your peers. There's music and people to talk to, but otherwise it isn't really like the movies. It's a... a Glass ring. You think it's a diamond, then you break it.
It's much, much more fun to go somewhere with friends and do all kinds of crazy shit together. Like go to concerts, go to a park after hours* and swing on swings, or lay around and play video games... There's plenty out there that's fun to do.
It just sounds to me like you're starving for friendship and/or popularity. Popularity isn't necessary for happiness, and if you're not actively trying to get it, you end up part of the in crowd, whether you want to be there or not.
2.) Man, ask her to do something with you. Don't try to sex her up on the first date, damn. But be like, "Hey, do you like pizza? because this place is fecking amazing!" or some shits. Just ask her to do something with you, and try to think of it as you're just going to do something fun with a friend. . . Or otherwise, find something random to do. Like, maybe there's some art center where you can make pottery or something. You get to be Creative* and there's plenty of time to just talk about whatever. Movies, music, school, DRAMA. Highschool is full of drama.
3.) I'm nervous about getting a job too, but I'm sure once I've been there a while I'll get over it... And so will you. XD I have faith in your skills bro, don't prove me wrong.
/end Tasty's Wall-O-Text.