Oh, high school. You would think society would've moved past the point of '80s teen comedies to a world where geeks and jocks could walk proudly hand in hand through the halls together. The cheerleaders and meathead football players standing slack-jawed; your fellow geeks cheering you on from the lockers. You take off your glasses and let down your hair, revealing that you're in fact not a dork, but actually a beautiful quirky princess who's finally found her studly prince. Then someone starts a slow cap, "Kiss Me" blares on the soundtrack, you kiss, and the credits roll.

It sounds like you are friends with this guy. Take it to the next level and ask him to hang out. Or start showing up at places where he hangs out (without seeming stalkerish) and strike up a conversation. What do you guys talk about? Maybe he's into some of the same things as you are. There's a great episode of the brilliant TV show Freaks and Geeks where cool guy slacker Daniel (James Franco) gets stuck playing Dungeons & Dragons with the geeks. Turns out he's great at it, and has a fun time. I'm not saying ask him to dress up like anime characters with you, but you might find that you both have the same taste in music or that he's, say, secretly a closet Lord of the Rings fan. Try to draw him away from his usual social circle by mentioning you're going to a cool new coffee shop or concert. Something that shows you have interests that set you apart from the self-involved cheerleaders and snotty rich girls he usually dates. (I'm assume you go to the high school in every teen movie ever made.)

If he turns you down, his loss. You will go away to college and "popular guy" will blow out his knee during the big game, fail to go pro, and stay in your hometown. Flash forward a few years, when you're cool and into "geeky" things (which, turns out, are actually fun, creative, and interesting) and you run into the "popular guy" at the local bar where everyone from high school who's home visiting their parents for Thanksgiving goes. But he's there every Friday night, not just the one after Thanksgiving. He'll buy you a drink and tell you about his three kids and failed marriage and his job as the assistant manager at Walgreen's. He thinks you're unique and cool, but you've moved on, and turn down his offer to come back to the tiny room he's living in above his cousin's garage, secure in the knowledge that he successfully peaked in high school. 

Or maybe you'll hang out now, fall in love, get married and have beautiful children together who can toss a football and program code.