Rafi (Uma Thurman) is a recently divorced, 37-year-old career woman from Manhattan. David (Bryan Greenberg), a talented 23-year-old Jewish painter from the Upper West Side, falls in love with her. Rafi shares all her secrets with her therapist Lisa (Meryl Streep). Unbeknownst to Rafi, Lisa happens to be David's mother.
Following the relationship of this unlikely couple, the story touches upon the difficulties of marriage and partnerships. It explores the possibility that love is not enough to make a relationship work and becomes a philosophical display of emotion and comedy.