- Directors: P J Hogan
- Genres: Comedy, Musical, Romance
- Actors: Julia Roberts, Dermot Mulroney, Cameron Diaz, Rupert Everett, Philip Bosco
Julianne Potter (Julia Roberts), a 27-year-old New York restaurant critic, receives a call from her longtime friend Michael O’Neil (Dermot Mulroney). In college, the two made an agreement that if neither of them were married by the time they turned 28, they would marry each other. Four days before her 28th birthday, Michael tells her he has fallen in love with, and is about to marry, Kimberly Wallace (Cameron Diaz), a 20-year-old University of Chicago student from a wealthy family. This causes Julianne to realize she has always been in love with Michael and cannot stand to see him wed another woman.
Julianne heads to Chicago, intent on sabotaging Michael’s wedding. Soon after arriving she meets Kimberly, who puts her on the spot and asks her to be the maid of honor. Julianne reluctantly agrees. This sets off a comical Jekyll and Hyde scenario, where Julianne must pretend to be the dutiful maid of honor while secretly scheming ways to prevent the wedding from happening. She engages in petty sabotage â€” for example, taking Kimberly and Michael to a karaoke bar after discovering Kimberly is a terrible singer, and making her sing in front of a large crowd â€” and later invites her gay friend George (Rupert Everett) to Chicago and pretends she is engaged to him, hoping to make Michael jealous.
At the wedding reception, Julianne makes a toast and finally bids goodbye to Michael, literally and figuratively. The bride and groom depart for their honeymoon, and Julianne is left sitting alone at a table. She receives an unexpected phone call from George, who is surreptitiously calling from an adjacent table, knowing that Julianne would be depressed. The two friends dance together as the film ends.