Drew is a recently divorced middle-aged Hollywood writer/director who arrives back in New York looking for a path to start his life over and upon arriving at his old apartment, finds three young women residing there until the end of the day. They are the free-spirited Lucy a multi-career woman and part-time actress who wants to move to Hollywood to start her life over; Annie is a photographer Lucy's best friend who wants to move to L.A. with Lucy, but unsure at what she wants to do with her life; Winona is a 30-year-old magazine editor who feels her biological clock ticking and wants to start a family. On his long day, an assortment of people soon arrive at the apartment for a party where they talk amongst each other about their stance in life in which Drew sees the inspiration from the conversations on deciding to start his life over.