Kissing A Fool is a 1998 American romantic comedy film directed by Doug Ellin. 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. 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.