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Miles Raymond, a failed writer and divorcé who teaches junior high school English takes his best friend, former hot actor Jack, on a weeklong drive up to California's wine country. There they explore the nature of their failures and question their relationships. Jack, about to get married, has an affair with a woman and wonders whether he should call off his wedding. Miles questions whether or not he made the right choice while trying to form a relationship with the woman's best friend, a fellow oenophile who is a waitress at a restaurant that he frequents often when visiting that part of the country.