Upset about his dating troubles, failing writer Marty Sachs (Ron Livingston) considers leaving New York City. At a party, he meets acerbic Nina Cohen (Cara Buono), who is just as bitter as Sachs. They begin seeing each other but Cohen, sensitive after past relationships, insists they take it slow. Marty also begins seeing Nina Harris (Amanda Peet), whom he finds physically attractive but less interesting. Unwilling to give up either Nina, Marty tries to conceal them from each other.