Helena Mora, the head of an eccentric theatrical family, has decided to sell her large estate in the Hamptons because of her recent money troubles. Before she completes the sale, she wants to have one last gathering of family and friends, with dramatic performances. Bringing everyone together, though, creates rivalries and tension, especially for Oona, a temperamental but successful movie actress who seeks the approval of her creative peers.

Naked in New York begins in the car of grown up Jake, he is talking to us about his girlfriend, Joanne, and to whom you can turn to for help while facing life. From there it flashes back to his memories of his parents, college, house across from a squirrel infested peanut factory, best friend, writing career and Joanne.

Jake takes out an ad in the newspaper after the suicide of his unfaithful fiancée, in an effort to understand the reasons for the betrayal. By soliciting the secret diaries of other women, he hopes to find some reconciliation with the truth.