A lonely writer quits his job at a Princeton prep school and sets his sights on New York, where he forges an unlikely bond with an eccentric playwright who now earns his living as an escort for wealthy Manhattan widows. Upon arriving in New York City, Louis Ives (Paul Dano) quickly lands a job at an environmental magazine and leases a room from Henry Harrison (Kevin Kline), a celebrated playwright without a penny to his name. Later, as Louis attempts to strike up a relationship with his environmentally conscious co-worker Mary (Katie Holmes), his urban education gets a sizable jump-start thanks to Henry, who spends his evenings with high-society widows hanging off both arms. As the bond between Henry and Louis strengthens, the young protégé realizes he isn't the only one gaining something from their unusual friendship.