Kissing A Fool (1998)

Max (David Schwimmer), an alpha-male commitment-phobic sports broadcaster, and Jay (Jason Lee), a neurotic novelist, have been best friends since childhood. Jay sets Max up with his editor Samantha (Mili 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. Though when Jay hits on Sam, they end up falling in love with each other.