The Opposite Sex tells 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 to 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.