"what would you do if you were stuck in one place and every day was exactly the same and nothing that you did mattered?"

A slacker on Slackers.

When an ambitious nerd with a bad crush discovers three fellow college students cheating the system, he blackmails them into helping him seduce the girl of his desire.

Makes Tomcats look like a Merchant-Ivory picture. Re-adjust the levels of cinematic hell, because Freddy Got Fingered just got bumped up a notch.