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. Three weeks before her 28th birthday, Michael tells her that in four days, he will marry Kimberly Wallace (Cameron Diaz), a 20-year-old University of Chicago student from a wealthy family.
Julianne is upset that Michael will marry someone so wrong for him, and someone he has known for such a short period of time. She realizes that she is in love with Michael, and heads to Chicago, intent on sabotaging his wedding. Soon after arriving she meets Kimberly, who asks her to be the maid of honor. This sets off a comical scenario in which 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 - for example, taking Kimberly and Michael to a karaoke bar after discovering that Kimberly is a terrible singer - and later asks her gay friend George Downes (Rupert Everett) to pretend they are engaged, hoping to make Michael jealous.
When these tactics fail, George convinces Julianne to do the obvious: tell Michael she is in love with him. On the morning of the wedding, Julianne confesses her love to Michael, asks him to marry her instead, and kisses him passionately. Kimberly witnesses this and runs off; Michael chases her, and Julianne pursues him unsuccessfully. Julianne finally accepts that she has lost Michael to Kimberly, so she apologizes to her and explains that she kissed Michael unexpectedly, but he didn't kiss her back because he loved Kimberly. Michael marries Kimberly, and Julianne wishes them well, consoled by her platonic friend George.
- Julia Roberts as Julianne Potter
- Dermot Mulroney as Michael O'Neal
- Cameron Diaz as Kimberly Wallace
- Rupert Everett as George Downes
- Philip Bosco as Walter Wallace
- M. Emmet Walsh as Joe O'Neal
- Rachel Griffiths as Samantha Newhouse
- Carrie Preston as Mandy Newhouse
- Susan Sullivan as Isabelle Wallace
- Chris Masterson as Scotty O'Neal
- Paul Giamatti as Richard the Bellman
- Harry Shearer as Jonathan P.F. Ritt
Some memorable quotes from imdb.com
Kimmy's Mother: I insist you stay on for lunch.
Julianne Potter: No, no, no, no, no... Absolutely -...
George Downes: Love to! Love the bag, love the shoes, love everything. Love to!
Julianne Potter: Michael... I love you. I've loved you for nine years, I've just been too arrogant and scared to realize it, and... well, now I'm just scared. So, I realize this comes at a very inopportune time but I really have this gigantic favor to ask of you. Choose me. Marry me. Let me make you happy. Oh, that sounds like three favors, doesn't it?
Kimmy Wallace: You kissed him!
Ladies in the bathroom: [gasps]
Kimmy Wallace: At my parents' house.
Ladies in the bathroom: [gasps]
Kimmy Wallace: On my wedding day.
Ladies in the bathroom: Bitch!
Ladies in the bathroom: Tramp!
Kimmy Wallace: I love this man, and there is no way I am going to give him up for some big-haired food critic.
Kimmy Wallace: I think I'm going to cry.
Julianne Potter: Me too.
George Downes: When you kissed Michael did he kiss you back?
Julianne Potter: What do you mean? We were lip to lip.
Michael O'Neill: Kimmy says if you love someone you say it, you say it right then, out loud. Otherwise the moment just...
Julianne Potter: Passes you by...
Michael O'Neill: Passes you by...
Julianne Potter: It is the duty of the best man to dance with the maid of honor.
Michael O'Neill: Dance? You can't dance. When did you learn how to dance?
Julianne Potter: I've got moves you've never seen.
George Downes: Kindred spirits, eh?
Julianne Potter: No, he's nothing like me. He's like you, actually, only straight.
Julianne Potter: I had the strangest dream. I dreamt that some psychopath was trying to break the two of you up. Luckily, I woke up and I see that the world is just as it should be. For my best friend has won the best woman. I didn't buy you a gift. But this is on loan until you two find your song...
Julianne Potter: I'm pond scum. Well, lower actually. I'm like the fungus that feeds on pond scum.
Michael O'Neill: Lower. The pus that infects the mucus that cruds up the fungus that feeds on the pond scum. On the other hand, thank you for loving me that much, that way. It's pretty flattering.
Julianne Potter: Except it makes me fungus.
Kimmy Wallace: He's got you on a pedestal and me in his arms.
George Downes: Tell him you love him. Bite the bullet.
George Downes: It's amazing the clarity that comes with psychotic jealousy.
George Downes: The misery, the exquisite tragedy. The Susan Hayward of it all. I can just picture you there, sitting alone at your table in your lavender gown.
Julianne Potter: Did I tell you my gown was lavender?
George Downes: Hair swept up. Haven't touched your cake. Probably drumming your fingernails on the white linen tablecloth, the way you do when you're really feeling down. Perhaps looking at those nails thinking: 'God, I should have stopped in all my evil plotting to have that manicure, but it's too late now.
Julianne Potter: George, I didn't tell you my dress was lavender.
George Downes: Suddenly, a familiar song. And, you're off your chair in one, exquisite movement... wondering, searching, sniffing the wind like a dapple deer. Has God heard your little prayer? Will Cinderella dance again? And then, suddenly, the crowds part and there he is: sleek, stylish... radiant with charisma. Bizarrely, he's on the telephone. But then, so are you. And then he comes towards you... the moves of a jungle cat. Although you quite correctly sense that he is... gay... like most devastatingly handsome single men of his age are, you think... what the hell. Life goes on. Maybe there won't be marriage... maybe there won't be sex... but, by God, there'll be dancing.
George Downes: Why don't we stop and have a drink? You can take a later flight.
Julianne Potter: No, no, no, no. I'm a busy girl. I've got exactly four days to break up a wedding, steal the bride's fella and I haven't one clue how to do it.
Julianne Potter: He just came in for few hours to uh, to uh, FUCK ME.
George Downes: Huh! Takes a few hours.
Julianne Potter: Crème brûlée can never be Jell-O. YOU could never be Jell-O.
Kimmy Wallace: I HAVE to be Jell-O!
Julianne Potter: You're never gonna be Jell-O!
Julianne Potter: You're going to humiliate me, aren't you?
George Downes: Only if I can.
George Downes: Maybe there won't be marriage, maybe there won't be sex, but by God there'll be dancing!
Kimmy Wallace: He sucks soup through his front teeth.
Julianne Potter: That's a trademark move - don't touch that one.
Kimmy Wallace: But he sure can kiss.
George Downes: The misery! The exquisite tragedy! The Susan Hayward of it all!
Julianne Potter: This is my one chance at happiness. I have to be ruthless!
George Downes: Hmm, death by mini-bar. How glamorous.
George Downes: Bond, Jane Bond
George Downes: Coffee anyone?
Kimmy Wallace: You kissed him! At my parents house! On my wedding day!
George Downes: Michael's chasing Kimmy?
Julianne Potter: Yes!
George Downes: You're chasing Michael?
Julianne Potter: YES!
George Downes: Who's chasing you... nobody, get it? There's your answer. It's Kimmy.
Julianne Potter: If he were feeling what I'm feeling then he would know how it feels.
Michael O'Neill: The ring.
[handing the box to Jules]
Julianne Potter: [nervous] Why are you giving this to me?
Michael O'Neill: Because I don't trust Scotty.
George Downes: [George is about to be introduced to Kimmy's family] Oh my god, race you to the altar!
Julianne Potter: [under her breath] Underplay.
George Downes: Got it.
[to a relative]
George Downes: HEY! How ya doin? I'm Jules' fiance! Just stopped by for a little conjugal visit!
Julianne Potter: Getting what you deserve is totally unfair.
Julianne Potter: You have been introduced to the symponic range...
Kimmy Wallace: Of his snoring?... Yeah, he says it's worse than ever
Julianne Potter: What I mean, when I say annoyingly perfect, is that there is nothing annoying about her perfection. It's vulnerable and endearing... and that is annoying as shit.
George Downes: Ahh... you like her...
Julianne Potter: If I didn't have to hate her, I'd adore her.