Comedy drama which follows Miles (Paul Giamatti), an unsuccessful novelist, and Jack (Thomas Haden Church), an equally unsuccessful actor who is about to get married. They decide to take a trip to California in an attempt to sow their wild oats. There they explore the nature of their failures and question their relationships. Jack has an affair and wonders whether he should call off the marriage. Miles, recently divorced himself, questions whether or not he made the right decision.