Holden Spence (Edward Norton) and Skylar Dandridge (Drew Barrymore) are a happy couple living in the city. Their best friends are another married couple, Steffi and Joe who also have a young child. After Joe and Steffi’s relationship ends, Joe moves to Italy and falls in love with a beautiful Italian girl. Steffi now single, becomes even closer with Skylar and introduces her to a friend of hers (Tim Roth) who has recently been released from jail. They fall in love and Skylar’s marriage also ends, leaving all of their friendships in serious jeopardy. It also forces them to come to grips with their wasted and immoral lives.