Longevity is no guarantee of fidelity, as Cal discovers when his 20-year marriage to Emily breaks down following her affair. He moves out and promptly goes to a bar to drink away his sorrows, pouring his heart out to the bartender. Upon hearing his woes, the suave and charming bar regular Jacob offers to help Cal get back in the game by giving him a makeover and teaching him how to be a player. Along the way however, it might just be possible that Cal finds true love again.