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.
Geoff Stults
as Vince
Mena Suvari
as Jane
Jennifer Finnigan
as Stephanie
Josh Hopkins
as Kenny
Eric Roberts
as Mr. Campbell
Kenan Thompson
as Mitch
Josh Cooke
as Kendrick
Debra Jo Rupp
as Tracy
Joey Fatone
as Delivery Guy
Tom DeNucci
as Reno
Jonathan Silverman
as Tom
Kristin Chenoweth
as Mrs. Kemp
