History Film / TwentySevenDresses

* PromotionToParent: Jane.

The story follows Jane Nichols (Heigl), a young single woman who's in love with her boss George (Edward Burns) but [[CannotSpitItOut doesn't have the courage to tell him]]. A notorious doormat, she has been a bridesmaid in 27 different 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's intrigued by the fact that she seems to be in two different weddings on the same night. Through a bizarre set of circumstances, the two share a taxi ride home, and Jane accidentally leaves her day planner behind. Kevin finds it and discovers her bridesmaid duties are a regular phenomenon.

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.

Soon after, Jane's spoiled and vain younger sister Tess (Malin Akerman), comes home to visit. She [[BoyMeetsGirl meets George and falls in love with him]], in spite of 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's got an ulterior motive: he is planning to write a story on the "perpetual bridesmaid", a piece that he believes will further his career.

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.

* LoveTriangle: Between Jane, George and Tess.

* MeaningfulName: Jane is supposed to be your typical "plain Jane" type.

* NoSparks: Jane and [[spoiler:George]].

* HorribleJudgeOfCharacter: George. Big time. He swallows every single lie that Tess tells him without question, so unfortunately he gets a ''very'' rude awakening when Jane puts together a slideshow that demonstrates just how much lying Tess has done since she met him. He is rightfully angry and becomes truly furious when he finds out she asked Pedro to do all the cooking and cleaning for them since she can't be bothered to do it herself. It's a wonder he's able to smile at her [[spoler: at the very end after all she put him and Pedro through, but it also shows what a NiceGuy he is that he eventually forgives her.]]

* HorribleJudgeOfCharacter: George. Big time.

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]].

* TheReasonYouSuckSpeech: After having to endure Tess lying to George to win him over and her constant demands for their upcoming wedding, Jane finally [[RageBreakingPoint snaps]] after Tess has the audacity to [[spoiler:cut up their deceased mother’s wedding dress (that Jane had been planning on wearing when she eventually got married) to make it more “modern”.]] After chewing her out, Jane gives Tess an ultimatum.
-->'''Jane:''' God, you don’t care! You don’t care about anyone but yourself, do you? I have made excuses for you because Mom died when you were little, but enough is enough!\\
'''Tess:''' I have no idea what you’re talking about.\\
'''Jane:''' I can’t undo what you’ve just done, but I won’t let you hurt George. He thinks he knows the truth about you, but all he knows are the lies you’ve told him! You even had ''Pedro'' keep a secret from George! You tell him the truth right now! He is not one of your Euro-trash boyfriends, Tess, he is a good person. And you cannot start a relationship based on ''lies''!\\

'''Jane:''' I’ve been to ''three''.

** Held by Kevin's editor, of all people. After Kevin [[HeelRealization begins to realize that he's treated Jane badly]] in his "perpetual bridesmaid" article, he calls his editor and asks her to hold the piece for a week. She agrees...then goes behind his back and runs the story anyway. Absolutely no justification is ever given for this; as someone on the Headscratchers page points out, the entire thing ends up feeling like a highly-contrived way to create tension between Kevin and Jane. Furthermore--and also appearing on the Headscratchers page-- publishing a story when an author has specifically requested it not appear opens the paper up to a big libel suit, something any editor worth their salt would know.

** Tess weaves an elaborate web of lies to make George believe that she's a healthy living, cooking and cleaning, outdoors-loving person. This works while they're dating and engaged, but what were her plans for ''after'' the wedding? Either she aims to change her lifestyle (which seems quite unlikely, since she'd constantly be doing things she hates) or to continue lying to George, which is ''bound'' to blow up in her face sooner or later.

* VillainBall: Held by Kevin's editor, of all people. After Kevin [[HeelRealization begins to realize that he's treated Jane badly]] in his "perpetual bridesmaid" article, he calls his editor and asks her to hold the piece for a week. She agrees...then goes behind his back and runs the story anyway. Absolutely no justification is ever given for this; as someone on the Headscratchers page points out, the entire thing ends up feeling like a highly-contrived way to create tension between Kevin and Jane. Furthermore--and also appearing on the Headscratchers page-- publishing a story when an author has specifically requested it not appear opens the paper up to a big libel suit, something any editor worth their salt would know.

* 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.

* HateSink: It is really, ''really'' hard not to completely hate Tess by the end of things. She's a spoiled brat who does not care about anything substantial, though it is at least suggested she sincerely likes George, but her behavior is reprehensible. She lies about every single thing about herself so he'll like her, fall in love, and marry her. She convinces his ward to do the cooking and cleaning so George won't find out she can't cook and clean. She expects Jane to plan her entire wedding without being paid for it and to get it done in ''only three weeks.'' She is fully aware that Jane had a dream wedding of getting married where their parents were married and wearing her mother's dress, then thinks it's fine to [[spoiler: ''cut up their mother's wedding dress'' and use ''parts'' of it for her own wedding.]] There is no excuse for that level of selfishness and there is no excuse for her being fine with lying to George throughout the entire relationship and if Jane hadn't [[spoiler: told George the truth]], Tess would have ''kept'' lying to George. The movie frames Jane [[spoiler: humiliating Tess in front of their family and friends]] as a bad thing, but honestly, Jane gave Tess every single chance to do the right thing and Tess chose not to do it. Tess' humiliation was fully earned by this point and she still doesn't even seem all that sorry for what's she's done by the end of things.

* AMinorKidroduction: the movie starts with Jane and Tess at their first wedding as kids. They see the bride in the bathroom with her dress ripped, so Jane takes Tess's hair ribbon to fix it. The bride then asks Jane to hold her train, showing the first time with her fate as a bridesmaid.

* 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.

* VillainBall: Held by Kevin's editor, of all people. After Kevin [[HeelRealization begins to realize that he's treated Jane badly]] in his "perpetual bridesmaid" article, he calls his editor and asks her to hold the piece for a week. She agrees...then goes behind his back and runs the story anyway. Absolutely no justification is ever given for this; as someone on the Headscratchers page points out, the entire thing ends up feeling like a highly-contrived way to create tension between Kevin and Jane. Furthermore--and also appearing on the Headscratchers page-- [[CriticalResearchFailure publishing a story when an author has specifically requested it not appear]] opens the paper up to a big libel suit, something any editor worth their salt would know.

* UnfortunateImplications: Invoked in-universe by Jane. George mentors a Latino boy named Pedro through Big Brothers Big Sisters, and at one point, Tess pays him to clean her apartment for her. During the speech/slideshow at the rehearsal dinner, Jane uses the information and a picture of the deed in question to deliberately suggest that Tess is racist for exploiting a Latino person for cleaning services.

* {{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.

* HateSink: It is really, ''really'' hard not to completely hate Tess by the end of things. She's a spoiled brat who does not care about anything substantial, though it is at least suggested she sincerely likes George, but her behavior is reprehensible. She lies about every single thing about herself so he'll like her, fall in love, and marry her. She convinces his ward to do the cooking and cleaning so George won't find out about it. She is fully aware that Jane had a dream wedding of getting married where their parents were married and wearing her mother's dress, then thinks it's fine to just ''cut up their mother's wedding dress'' and use ''parts'' of it for her own wedding. There is no excuse for that level of selfishness and there is no excuse for her being fine with lying to George throughout the entire relationship and if Jane hadn't [[spoiler: told George the truth]], Tess would have ''kept'' lying to George. The movie frames Jane [[spoiler: humiliating Tess in front of their family and friends]] as a bad thing, but honestly, Jane gave Tess every single chance to do the right thing and Tess chose not to do it. Tess' humiliation was fully earned by this point and she still doesn't even seem all that sorry for what's she's done by the end of things.

* HateSink: It is really, ''really'' hard not to completely hate Tess by the end of things. She's a spoiled brat who does not are about anything substantial, though it is at least suggested she sincerely likes George, but her behavior is reprehensible. She lies about every single thing about herself so he'll like her, fall in love, and marry her. She convinces his ward to do the cooking and cleaning so George won't find out about it. She is fully aware that Jane had a dream wedding of getting married where their parents were married and wearing her mother's dress, then thinks it's fine to just ''cut up their mother's wedding dress'' and use ''parts'' of it for her own wedding. There is no excuse for that level of selfishness and there is no excuse for her being fine with lying to George throughout the entire relationship and if Jane hadn't [[spoiler: told George the truth]], Tess would have ''kept'' lying to George. The movie frames Jane [[spoiler: humiliating Tess in front of their family and friends]] as a bad thing, but honestly, Jane gave Tess every single chance to do the right thing and Tess chose not to do it. Tess' humiliation was fully earned by this point and she still doesn't even seem all that sorry for what's she's done by the end of things.