It primarily stars David Schwimmer, Jason Lee, Mili Avital, Kari Wührer, and Vanessa Angel.

Max (David Schwimmer), an alpha-male commitment-phobic sports broadcaster, and Jay (Jason Lee), a neurotic novelist, have been best friends since childhood in Chicago.

Jay has just broken up with his girlfriend, Natasha (Vanessa Angel) and is writing his first book about their relationship in Milan, Italy.

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.

Later, Jay crashes at Sam's, and after finishing reading the manuscript, she goes upstairs to talk to him, and before they have a moment where they almost kiss, her cousin Dre interrupts them.

Max is shocked but then he starts to laugh, thinking it's a joke, spilling the beans about the fidelity test he'd asked Jay to do on her.

In the closing scene, Max gives them his blessing at their wedding, remarking "Love cannot be found where it doesn't exist.

The Original Motion Picture Soundtrack was released on March 24, 1998, with music composed by Joseph Vitarelli.

Other notable songs not featured in the soundtrack include: Filmed in Chicago, Illinois, Kissing A Fool utilises several locations within the area.