The Opposite Sex (1956)

Director: Jonathan Silverman, Jennifer Finnigan
Cast: Dana Ashbrook, Eric Roberts, Geoff Stults, Jennifer Finnigan, Josh Hopkins, Kenan Thompson, Kristin Chenoweth, Mena Suvari

Synopsis:

The story of Vince, New England’s most successful divorce attorney. To Vince, life is one big competition, and losing is unacceptable. This also applies in his dating life with his love ’em and leave ’em approach. Then Vince meets Jane, who is beautiful, successful and also extremely driven. Together they enter into a series of entertaining wagers with each other where the winner gets to decide the fate of the loser.