Julianne Potter (Roberts) is a restaurant critic from New York who, turning 28, realizes she's getting dangerously close to being a stale Old Maid. In college she and her best friend, Michael O' Neal (Dermot Mulroney), had made a pact that the two of them would marry each other if neither of them were married by the time they reached 28. He calls close to her birthday... only to tell her that he's found a pretty, wealthy, cheerful young bride in the person of Kimberly Wallace (Diaz), who wants her to be her maid of honor. A Green-Eyed Epiphany follows. She heads to Chicago, to not only be said maid of honor, but also try and sabotage the wedding and get Michael for herself. Hilarity Ensues.
The film opened, embarrassingly, behind Batman & Robin in theaters, but went on to make nearly $300 million at the box office. It also received mostly positive reviews.
This film provides examples of:
- Almost Kiss: Lampshaded; "sometimes the moment just... passes you by."
- The Beard: Julianne asks George, her Gay Best Friend, to pretend to be her boyfriend to make Michael jealous.
- Best Woman: According to Michael's father, Julianne was close to becoming one. Can you say "friend-zone?"
- Bittersweet Ending: Julianne gives up on Michael and he goes on to marry Kimberly, making amends to both for her actions. While she's happy for the two, is visibly saddened that she did not get the guy she's been fawning over since college. However George, probably sensing this, quickly books a flight back to Chicago from London and arrives at the reception to come cheer her up.
- Chewing the Scenery: George, while demonstrating a guy he knew who thought "He was Dionne Warwick". It gets contagious.
- Chick Flick: Romance, weddings, karaoke, etc.
- Clingy Jealous Girl: Julianne can't stand the thought of any girl with Michael that is not herself.
- Cool Big Sis: Kim really wants Julianne to become this to her. Little did she know Jullianne exploited the position to give her bad advice.
- Crowd Song: "I Say A Little Prayer." It's the gay guy that starts it off to try to make the ruse of being Julianne's boyfriend convincing. The rest just join in and even the restaurant staff help out by providing the music.
- Derailing Love Interests:
- Invoked, as Julianne plots Relationship Sabotage by derailing Kim.
- Averted regarding Julianne, who shows clear signs of being a psycho bitch through the film (which are at first concealed by our expectations of the genre), and the script is not shy about how bitchy she is... But that is the point. Julianne gets chewed out for her actions. The Gay Best Friend constantly tells her that her idea is stupid, the Nice Guy is upset when Hell breaks loose, and when Julianne has to confront Kim on the shit she did to her, all the women in the scene side with Kim and call Julianne "bitch", "slut" and "couple breaker" in the most hilariously awesome way ever possible.
- Did Not Get The Guy: Julianne, our Villain Protagonist, does not marry her best friend.
- Fag Hag: Julianne's best friend (apparently her Only Friend aside from Michael) is the homosexual George.
- Fallback Marriage Pact: The setup for the whole plot; Julianne is still single when the pact expires but Michael is not.
- Fiery Redhead: Julianne's temper is shorter than Hair of Gold, Heart of Gold Kimberly and she is more prone to shouting.
- Focus Group Ending: Executive Meddling wanted Julianne to get together with a random guy at the wedding reception, but audiences didn't like it, so the originally-written ending where her gay friend George comforts her was made instead.
- Fourth Date Marriage: Part of the reason Julianne is so mad that he'd marry Kimberly, since he barely knew her while she and Michael have been friends for years already.
- Genre Deconstruction: A romantic comedy where the protagonist comes to realise that she is the Romantic False Lead. Several Zany Schemes are scuppered when Reality Ensues and/or the couple make up because they're genuinely in love.
- Getting Crap Past the Radar: Kimmy snuck out without anyone noticing because everyone was more focused on a woman who got her tongue stuck to an ice sculpture of Michelangelo's David.
- Green-Eyed Epiphany: While Julianne knew Michael might have feelings for her, she thought of him as her best friend until she heard he was getting married.
- Heel Realization: At one point, Julianne even says "I'm the bad guy."
- Helium Speech: The boys sing a ballad with helium sucked from the wedding's balloons.
- Heroic BSoD: Happens to Kim, when Julianne kisses Michael. The poor girl runs away in tears and disappears.
- Hollywood Tone-Deaf: Kimberly is an aversion. Cameron Diaz's karaoke sounds realistically off.
- Ignored Epiphany: There are several moments during the film where Julianne appears to realize how awful the things she is doing are, but they don't really stick until the end.
- Irrevocable Message: Julianne sends an e-mail from Michael's account in an attempt to cause trouble between him and Kim. She realizes how wrong it was once it's too late.
- It's All About Me: Julianne is all about this trope. She wants Michael for herself, and is willing to do anything to get him. Who cares that he's in love with (and about to marry) someone else?
- Must Make Amends: Julianne forcibly kisses Michael. Kimberly catches them, believes he's cheating on her, and runs away in the middle of an Heroic BSoD. Julianne realizes that Michael really cares for Kim, so she's the one who has to convince Kim to come back for Michael's sake. By the time the two met again, Kim had decided to fight back for Michael. Most of what Julianne did at that point was to assure her that she just kissed Michael suddenly when he wasn't expecting it and that Michael never kissed her back, and to let Kim know that she was giving up.
- No Sympathy: This is subverted in the karaoke scene. The crowd's initial response to Kimberly's Hollywood Tone-Deaf singing is a humiliating stunned silence, but then they start to cheer and clap and she starts to laugh along with them.
- Old Maid: Julianne didn't care about her age and not being married yet... until Michael told her "I'm getting married to Kim, whooo!"
- Poor Communication Kills: Subverted. Julianne engineers a huge row between the fiancés, but just as Michael is about to storm off, Kimberly bursts into tears and apologises.
- Precision F-Strike: When Jules is trying to convince Michael and Kimberly that her gay male friend is really her boyfriend. "He's coming over to um fuck me."
- Protagonist Journey to Villain: Jules's schemes get more diabolical and mean-spirited as the film goes on to the point where she is basically a Villain Protagonist. She gets better by the end.
- Relationship Sabotage: The whole plot is about Julianne's attempt at breaking up the engaged couple.
- Romantic False Lead: The subversion of this ends up being the crux of the story. One expects the two leads to hook up as Victorious Childhood Friend and the third to be a Disposable Fiancé, but that is not the case here.
- Springtime for Hitler: Julianne arranges for Kimberly to humiliate herself at a karaoke bar, but (what with it being a karaoke bar) everyone cheers and applauds her awful singing and Michael looks impressed that she has guts to go along with it.
- Villain Protagonist: The major gimmick of the film is having the Romantic False Lead as the main character.
- What the Hell, Hero?:
- As said before, the script does not try to pass Julianne's actions as acceptable, and that goes double for the characters after she kisses Michael. Which leads to a rather funny scene in a ladies bathroom:Kim: You kissed him [Michael]!
Kim: In my parent's house!
Kim: ON MY WEDDING DAY!
Spectators: [GASP!!] Bitch Tramp
- George tells Julianne right off the bat he doesn't approve of what she's doing when she ropes him into her scheme. It's implied he deliberately overdoes the acting while posing as her boyfriend in the hopes Julianne will come to her senses.
- As said before, the script does not try to pass Julianne's actions as acceptable, and that goes double for the characters after she kisses Michael. Which leads to a rather funny scene in a ladies bathroom: