Nick (MICHAEL CERA) is a normal teenage guy -- save for the fact that he's the lone straight member of the gay band The Jerk-Offs that's comprised of Thom (AARON YOO), Dev (RAFI GAVRON) and new follower Lethario (JONATHAN B. WRIGHT) -- who's fixated on and longing for his ex-girlfriend.
She's Tris (ALEXIS DZIENA) who's grown tired of him continually sending her CD mixes of songs and his verbalized thoughts about her. Her schoolmate Norah (KAT DENNINGS), however, thinks the mixes are good even if she's never met their creator. Yet she eventually does just that, albeit by dumb luck, when Tris is showing off her new boyfriend and making fun of Norah for not having one, considering that her ex, Tal (JAY BARUCHEL), is now just a "friend with benefits."
In a moment of desperation, she spots Nick and asks if he'll be her boyfriend for five minutes, all to get Tris off her back. His band-mates think they'd make a cute couple and hate seeing him pine away for Tris who they can't stand, so they agree to take Norah's drunk friend Caroline (ARI GRAYNOR) home so that Nick and Norah can get to know each other.
As they spend the rest of the night and early morning together bickering and traversing their way through New York City looking for their favorite band's next guerilla performance and then Caroline when she ends up missing, the two teens start to develop feelings for each other and must decide who they want in their romantic lives.