Kissing a Fool Cast

David Schwimmer plays Max Abbitt, a commitment-phobic sportscaster who makes a bet that his best friend can't stay faithful to his new girlfriend.

Jason Lee portrays Jay Murphy, a successful novelist who becomes the subject of a bet between his best friend and a colleague.

Mili Avital takes on the role of Samantha Andrews, Jay's new girlfriend who unwittingly becomes the focus of a wager between friends.

Bonnie Hunt appears as Linda Streicher, Max's no-nonsense agent who provides him with guidance and support throughout his romantic entanglements.

Vanessa Angel plays Natasha, a glamorous and alluring woman who captures Max's attention at a critical moment in his relationship.

Judy Greer portrays Andrea, a friend of Samantha's who offers advice and perspective on the challenges of modern dating.

Kari Wuhrer takes on the role of Dara, a bartender who provides Jay with an unexpected opportunity for personal growth.

Frank Medrano appears as Cliff Randal, a tough and no-nonsense colleague who becomes embroiled in the romantic bet between friends.

Bitty Schram portrays Vicki Pelam, a friend and confidante who offers support and insight to the main characters as they navigate their romantic challenges.

Jerry Springer makes a cameo appearance as himself, adding a touch of reality TV drama to the unfolding romantic comedy.

Sammy Sosa also makes a cameo appearance as himself, adding a touch of star power to the comedic proceedings.