In this romantic comedy, wealthy Chicago publisher Linda (Bonnie Hunt), hosting a wedding at her suburban estate, narrates the tale of how the couple arrived at the altar: Womanizing sportscaster Max (David Schwimmer) and novelist Jay (Jason Lee), friends since childhood, have different attitudes toward women. Incurable romantic Jay still carries a torch for his departed girlfriend Natasha (Vanessa Angel) and is unable to picture himself with any woman in the future. When Jay matches Max with his book editor Samantha (Mili Avital), the two strike such sparks that they get engaged within 14 days. The thought of settling down puts Max in such a panic that he proposes a peculiar loyalty test -- one that involves Jay seducing Sam. If Sam remains faithful to him, then he will proceed with the marriage. Jay doesn't agree to this, but book revisions keep bringing him together with Sam, forcing them to deal with the way they really feel about each other. Director Doug Ellin (Phat Beach) filmed at locations in Chicago.