Louis Ives (Paul Dano) heads to New York City following an embarrassing incident that forces him to leave his job. He rents a room in the apartment of Henry Harrison (Kevin Kline), a penniless, wildly eccentric playwright, and accepts a position with an environmental magazine, where he encounters green-obsessed Mary (Katie Holmes). But it's Louis' new home life with Henry that really sparks his imagination. Developing a mentor/apprentice relationship, Henry exposes Louis to the duties of an "extra man," a social escort for wealthy society widows.
