Julianne Potter (Julia Roberts) is a successful and independent food critic. Her closest friend is George (Rupert Everett), who happens to be gay. Over dinner with George, she reminisces about another relationship in her past: her brief romance and long-term friendship with Michael ONeal (Dermot Mulroney), a freelance sports writer. Jules and Michael were such good friends, they made a half-serious promise to each other that if neither found a mate before they turned 28, they would marry each other. Soon afterward, Jules receives a call from Michael, who tells her he has met that special someone -- Kim Wallace (Cameron Diaz), the daughter of a billionaire baseball team owner. Michael is madly in love with Kim, but asks his "best friend" to visit him in Chicago to lend him support. Jules is shocked to hear this news, and suddenly becomes desperate to win Michael for herself. She travels to Chicago, meets Kim, and realizes that this girl really is perfect, not just to Michael. Nevertheless, she embarks on a campaign to turn Michael and Kim against each other. George joins her, and attempts to help her face the truth about what will make her feel good for the immediate moment and in the long term. As the wedding date approaches, Jules becomes more desperate, but her attempts fail. However, just before the wedding, Michael gets a message that throws his relationship with Kim seriously into doubt...and gives Jules her chance to share her true feelings with Michael. This romantic farce features the music of Burt Bacharach.