Stillman is also in love with the Girl of His Dreams. Problem: she just dumped him. Does he man up and move on? Stand outside her window with a boom box? Nope, he and Evan build a time machine and go back to see where things went wrong. Dude, maybe you're just not compatible.
Maybe it was that double-date where you insulted the Girl's bffs (she has one of each, girl and gay guy). So they relive the moment, and other similarly prescient moments, a bazillion times. Every argument, every mior disagreement has to be ironed out. Wait -- he's basically conning this girl. How would you like it if someone kept re-arranging your life events without your permission?
Meanwhile, Evan meets the Girl of His Dreams and keeps using the time machine to redo every less-than-perfect moment. Guess what? They're all less than perfect.
Stillman finally realizes that going back in time was a bad idea: people get hurt, they hurt others, life is life. How profound! He wants to destroy the time machine, but Evan wants to keep it. They argue, break up, and reconcile.
They end up stuck in the past, having to relive the events that they've been playing all over again. But if they let life happen and not worry about making it perfect, maybe they can relax and have fun. Fade-out boy-girl kiss. Darn, I thought Stillman and Evan would finally recognize their love.
Heterosexism: A double-dose of 1980s teen nerd Girl of His Dreams, completely drowning out the gay subtext romance.
Gay Characters: Remember the Girl's gay bff, Ryan (Will Peltz)? He gets a boyfriend, too, and he doesn't even have to use a time machine.
I'm not sure about this next one, so I'm putting it under a jump break