''27 Dresses'' is a RomanticComedy, released in 2008, starring Katherine Heigl and James Marsden.

The story follows Jane Nichols (Heigl), a young woman in love with her boss George, but she [[CannotSpitItOut does not have the courage to tell him]]. A notorious doormat, she has been a bridesmaid in 27 weddings, usually shouldering much of the responsibility for planning the weddings as well. We're introduced to Jane the same night she meets Kevin Doyle (Marsden), a cynical young man who covers weddings for the local paper (though Jane is unaware of this). He is intrigued by the fact that she seems to be in two different weddings on the same night. Through a bizarre set of circumstances, they share a taxi ride home. Jane accidentally leaves her planner/calendar behind. Kevin finds it and realizes her bridesmaid duties are a regular phenomenon.

Soon after, Jane's spoiled and vain younger sister Tess (played by Malin Akerman), comes home to visit. She [[BoyMeetsGirl meets and falls in love with George]], despite the fact that they are complete opposites. Tess continually lies to George to convince him that they are soulmates, much to Jane's dismay. Meanwhile, Kevin has been using Jane's calendar to find her and continually hound her for a date. Unfortunately, he has an ulterior motive. He is planning to write a story on the "perpetual bridesmaid", a piece that he believes will further his career.

After a very short courtship, George proposes to Tess, who of course assumes that Jane will plan everything for their wedding to be held in several weeks. Jane's emotional state deteriorates rapidly, while Tess' diva behavior increases dramatically. On top of that, Jane learns Kevin is actually a wedding journalist who plans to cover George and Tess' wedding (though still unaware of the perpetual bridesmaid article he plans to write). Kevin eventually deduces that Jane is in love with George, and pushes her to stand up for herself and what she wants. At the same time he asks his editor to hold the article about Jane. He is beginning to realize that there's more to her than he first thought, and the article doesn't portray her in a flattering light. His editor says she'll hold the story, but unbeknownst to Kevin, goes back on her word and publishes it anyway.

While running an errand, Jane and Kevin get stuck overnight due to weather, and realize they have feelings for each other, [[RelationshipUpgrade which they act on]]. But the following morning, Jane sees the article. She's understandably humiliated, and leaves him. Tess is furious with her for allowing herself to be manipulated, which furthers her depression. But when Jane finds out that Tess has cut up their mother's wedding dress (which she had planned to wear to her own wedding), she comes to her senses and realizes that George needs to know the truth. At the rehearsal dinner that night, Jane gives Tess one more chance to come clean. She refuses, so Jane proceeds to humiliate Tess during her speech with a slideshow that vividly demonstrates the lies Tess has fed George. The wedding is called off.

Eventually the girls' father forces them to see each other and work out their differences. Tess learns that she needs to be less selfish and more compassionate before she deserves a guy like George. Jane realizes that Kevin was right, and she needs to learn to take care of others without completely ignoring herself. Later that evening George invites Jane to a charity event, as he needs a date. She meets him at the office, where she finally confesses her feelings for him. He kisses her, but they both realize they have zero chemistry. Jane realizes Kevin is actually the right guy for her, and she [[TheyDo ends up with him instead]].
!!This film shows examples of the following tropes:

* ArmorPiercingSlap: One PlayedForLaughs from Casey to Jane when she's mooning over George. Later on, Jane herself gives one to Kevin after she finds out about the article.
* AtomicFBomb: Jane becomes so pissed off about the fact that Kevin sent her flowers instead of George that she leaves the party temporarily to scream one in the hallway.
* AnguishedDeclarationOfLove: Jane couples George's with a "quitting my job" speech, then gives [[spoiler:Kevin a real one minutes later.]]
* BigApplesauce: Set in New York, with the wedding to be held in Central Park.
* BitterWeddingSpeech: The main character gives a very sarcastic and bitter speech (which was actually written by the sister to be said under different circumstances so that the main character wouldn't "embarrass" her) at her sister's rehearsal dinner, revealing to her sister's fiancé that she (the sister) has been lying to him about various things and causing him to break off the engagement.
* BlondeBrunetteRedhead: Tess, Jane and Casey respectively. Each with typically associated personalities.
* BouquetToss: One of these gone wrong is how Kevin and Jane meet.
* {{Bridezilla}}: Tess. Oh God, Tess. It even gets mentioned by name in the article Kevin writes.
--> '''Tess''': Someone alert sky traffic because Bridezilla is on the loose!
* BrilliantButLazy: Casey. She's a free-spirited and lazy HardDrinkingPartyGirl who ReallyGetsAround, and yet in an easily-missed line, it's revealed that she's an ''accountant''.
* BrokenPedestal: Jane is horrified to learn that the deeply cynical Kevin (using a pen name) is the one who writes the wedding articles she reads.
-->'''Jane:''' It's like finding out my favorite love song was written about a sandwich...
* BuxomIsBetter: Jane mentions an aunt used to joke about Jane having small breasts, which seems ridiculous now. What's even stranger is that it's Tess that brings this up, even though Jane is significantly bigger than her.
* CantLiveWithThemCantLiveWithoutThem: Part of Jane's speech to [[spoiler:Kevin]].
* CaughtInTheRain: This is exactly how Jane and Kevin first hook up.
* ConsummateLiar: Tess continuously lies and bullshits George about being a healthy-living, outdoorsy girl, much to Jane's chagrin. Naturally, this blows up in her face.
* CynicismCatalyst: Kevin's cynicism regarding weddings is because [[spoiler:he had his big fancy wedding planned, but then his bride left him for his roommate]].
* DeadpanSnarker: Kevin.
** Also Jane.
--> '''Jane''': Do you also go around telling small children that Santa Claus doesn't exist? 'Cause someone needs to blow that shit wide open.
* EveryoneCanSeeIt: Everyone knows how Jane feels about George.
** Except George, who's completely ObliviousToLove.
* ExtremeDoormat: Jane, of course.
* FoolishSiblingResponsibleSibling: Jane is the elder, responsible sister and her younger sister Tess is Foolish.
* FourthDateMarriage: Tess and George go from dating to engaged to wedding in an alarmingly short time.
** Jane and [[spoiler: Kevin]] are a subverted example. They marry a year after they get engaged.
* GentlemanAdventurer: George is a well-done modern version of this.
* GiantPoofySleeves: Many of Jane's dresses have giant pouffy sleeves, like the southern belle dress and teal dress.
* TheGloriousWarOfSisterlyRivalry: Jane's PromotionToParent averted this when they were young, but said war is declared and played straight during the movie's events.
* {{Goth}}: Gina, the secretary at Jane and Casey's job. Even her wedding is gothic.
* IDidWhatIHadToDo: Jane's justification for publicly humiliating Tess. It's clear that even she doesn't buy this explanation and realizes there were other methods to achieve her goal.
* IMissMom: Even though they were quite young when their mother passed away (Jane was eight and Tess was several years younger), her loss is implied to be a huge factor in Jane's personality, a cause of sadness in the family (especially for their father), and a significant contributor to several plot points.
* KimonoIsTraditional: One of Jane's bridesmaids dresses is a purple kimono that she wore at traditional Japanese wedding.
* MeaningfulName: Jane is supposed to be your typical "plain Jane" type.
* MissingMom: Jane and Tess's mom died when they were young.
* MomentKiller: Kevin. Jane's overreaction is what makes him realize she has feelings for George.
* {{Mondegreen}}: An excellent lampshading of this occurs after Kevin and Jane get wasted in a bar and both demonstrate that they have no idea what the real lyrics are to "[[Music/EltonJohn Bennie and the Jets]]". But that doesn't stop them from singing and dancing to it anyway.
* NoSparks: Jane and [[spoiler:George]].
* PairTheSpares: Jane's loose friend Casey and Kevin's girl-crazy co-worker Trent are implied to hook up at the end.
* PimpedOutDress: Some of Jane's bridesmaid gowns, a few of them pimped to [[ImpossiblyTackyClothes truly epic/horrific proportions]].
* PluckyComicRelief: Casey. She does give Jane some much needed advice more than once in the story, though.
* PromotionToParent: Jane.
* RaceForYourLove: Jane uses a taxi and jumps a boat ramp in high heels during her race [[spoiler:to get to Kevin]] at the end of the movie.
* RageBreakingPoint: Jane's personality and upbringing are the reasons she can stay so calm throughout the whole movie, even when she's grinding her teeth to respond, but when [[spoiler:she finds out that Tess cut up their deceased mother's wedding dress to make it more "modern"]] she finally [[TheReasonYouSuckSpeech cracks]].
* ReallyGetsAround: Casey, unashamedly so.
* SiblingTriangle
* SiblingYinYang: Jane is smart, responsible, and selfless, while Tess is irresponsible, selfish, and carefree.
* TestKiss: Jane and George, after Jane finally confesses her feelings for him; [[spoiler: they mutually decide there's no spark.]]
* WasItAllALie: Jane asks Kevin this after she sees his article about her. She doesn't believe him when he says "no".