Peter Burton (Cusack) and best friend Tim Garrity (Spader) nervously await the results of Peter's 1990 congressional election. Tim is telling the story of how they all came to such a thing. The two met seven years earlier following an argument in the parking lot at the University of Virginia law school. After discovering that they are to be roommates, the men become close friends. Peter makes Tim believe he lives a privileged life as well. At Christmas, he claims to be travelling to London with his father participating in "some World Bank thing" when in actuality, he spends the entire holiday alone at school, often researching Senator Stiles, his family and staff. Peter attends a New Year's Eve party at the Stiles residence and shares an inappropriately long kiss with Diana that Tim does not notice. Later, when Tim decides to take them to a working class bar to continue celebrating, Peter is recognized by his ex-girlfriend and her husband, also an old friend of Peter's. An exposed and embarrassed Peter admits that his name is actually Burtowski and that he lied about his entire life. Tim is angry but soon after he forgives Peter and tells him that he understands. Tim plans a career with the Department of Justice, a fact that doesn't sit well with his girlfriend, Diana (Imogen Stubbs), the daughter of Senator Stiles (Widmark). Both men land dream internships is Washington, Peter with Senator Stiles' office and Tim at DOJ. Some of Peter's true nature is revealed while they are there and at the end of the summer, Peter decides to stay in DC and not complete law school. Tim intended to propose to Diana on a sophisticated date night but her doubts about his career plans make him realize she would turn him down and he keeps the ring and his marital intentions secret.