Max (Schwimmer), an alpha-male commitment-phobic sports broadcaster, and Jay (Lee), a neurotic novelist, have been best friends since childhood. Jay sets Max up with his editor Samantha (Avital). Although they share few interests, they are engaged within two weeks. Still, when Max is confronted with the fact that Sam will be the last woman he will sleep with, he proposes a test: Jay will hit on Sam. If she shows no interest, then Max will be confident enough in her loyalty to go ahead with the marriage. However, while Jay initially doesn't want to, it doesn't take long before trouble arises.
This film features examples of:
- Cluster F-Bomb: Max's retort to Jay's comment about something being fair:Max: Fair? You're telling me that the girl I wanna marry is thinkin' about fucking my best friend?! Fuck fuckin' fair! Fuck you! Fuck her! Fuck everybody fair!
- Drowning My Sorrows: Jay does this to an absurd degree.
- Fidelity Test: Pretty much the whole plot of the movie is that Max enlists Jay to test his fiancée Sam's loyalty by trying to seduce her.