Don't dwell on perceived popularity differences.
Your perceived notions about old hierarchy systems are played out, dude.
You might have been that awkward goth kid who didn't figure how his penis worked until college, but you're an adult now. You wear matching socks, and more importantly, you've evolved into a more self-aware human being. Instead of remembering the stereotypes about the social groups you two fit in years ago, and then acting on them, focus on your current steez (and hers). Forget marching band and the bad acne.
Yes, this means you can (and should) go for the girl you once considered out of your league. LEAGUES ARE ALL IN YOUR MIND. Mostly.