Susan Sullivan as Isabelle Wallace, wife of Walter, mother of Kimmy, and future mother-in-law of Michael.
Carrie Preston as Amanda Newhouse, twin sister of Samantha and one of Kimmy's bridesmaids.
Rachel Griffiths as Samantha Newhouse, twin sister of Mandy and one of Kimmy's bridesmaids.
He suggested that Julianne be Michael's best man, but had to go with Scotty instead. Emmet Walsh as Joe O'Neal, father of Michael and Scotty O'Neal and future father-in-law of Kimmy. He is a rich businessman who owns the Chicago White Sox baseball team.
Philip Bosco as Walter Wallace, husband of Isabelle, father of Kimmy, and future father-in-law of Michael.
Rupert Everett as George Downes, Julianne's gay friend and editor who pretends to be engaged to Julianne to make Michael jealous.
Cameron Diaz as Kimmy Wallace, Michael's bubbly and lovable fiancée who comes from an affluent family.
Dermot Mulroney as Michael O'Neal, Julianne's best friend and a sportswriter who is engaged to Kimmy Wallace.
Julia Roberts as Julianne Potter, a 27-year-old food critic who realizes she's in love with her best friend Michael and tries to win him back after he decides to marry someone else.
On the phone with George, Jules is surprised to see him at the reception, and they dance together. Jules and Michael share their goodbyes, both finally moving on. Jules allows the newlyweds to temporarily have "The Way You Look Tonight" as their song until they find their own song. The wedding proceeds, and at the reception, Jules gives a heartfelt speech as Kimmy's maid of honor. Jules apologizes, assuring Kimmy that Michael truly loves her, and they reconcile. Amid a crowd of onlookers, Kimmy confronts Jules for interfering with Michael. Jules finds Kimmy in the bathroom of Comiskey Park. He forgives her and tells her that here at the station is where he proposed to Kimmy and she accepted, and they split up to look for Kimmy. Finding Michael at Chicago Union Station, Jules confesses to everything. Jules calls George, who assures her that Michael loves Kimmy. Kimmy witnesses this and drives away, pursued by Michael, who is followed by Jules in a caterer's truck. Jules finally confesses her love to Michael and passionately kisses him. She tries to manipulate the couple into breaking up for good, but Michael and Kimmy decide to get married after all. The next morning, Jules discovers that neither Michael nor Kimmy have told anyone else that the wedding is off. Furious, he calls Kimmy, calling off the wedding. Returning to Jules' hotel, Michael receives a message from his boss notifying him of the email. Jules lies to enlist Michael's help, but they find the office locked. She saves the message rather than send it, but later realizes that Kimmy's father has unknowingly sent the email. The day before the wedding, at Kimmy's father's office, Jules uses his email account to forge a message from him to Michael's boss, asking that Michael be fired to allow Kimmy's father to hire him at Kimmy's insistence. They share a dance as Michael sings their song, " The Way You Look Tonight". Michael admits to feeling jealous and gives her the chance to confess her own feelings, but she lets the moment pass. George flies home, and Jules tells Michael that her "relationship" with George is over. George, who is gay, plays along but embarrasses Jules at lunch with the wedding party, singing " I Say a Little Prayer" as the whole restaurant joins in. On George's advice, Jules prepares to tell Michael how much she loves him, but instead tells him that she is engaged to George, hoping to make Michael jealous. She manipulates Kimmy into asking her father to offer Michael a job, which Jules knows will anger Michael, but this fails as well.įrustrated, Jules begs her friend George Downes for help, and he flies to Chicago. Jules schemes to break up the couple, but her attempt to humiliate Kimmy at a karaoke bar backfires. Arriving in Chicago, she reunites with Michael and meets Kimmy, who asks her to be the maid of honor. Realizing that Michael is the love of her life, Jules resolves to sabotage his wedding. Michael tells her that in four days, he will marry beautiful Kimmy Wallace, a college student eight years his junior whose father owns the Chicago White Sox. Years earlier, the two agreed that if they were both unmarried by age 28, they would marry each other. Three weeks before her 28th birthday, New York City food critic Julianne "Jules" Potter receives a call from her lifelong friend Michael O'Neal, a Chicago sportswriter.