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Giselle (Amy Adams) lives in the blissful animated world of Andalasia, where magical beings frolic freely, animals are talkative companions and musical interludes punctuate every interaction. She dreams of her true love and builds a statue wearing a blue jacket to represent him from her dream with the help of her chipmunk friend Pip and other forest animals. She sings about her true love's kiss, and Prince Edward (James Marsden), a handsome and valiant but dimwitted prince, hears her voice in the forest and rescues her from a troll. Giselle and Edward get engaged, but her fate takes a turn for worse on her wedding day when his stepmother, the villainous Queen Narissa (Susan Sarandon), throws her through a magic portal to a place where there is no happily ever after in order to keep her step son single and thus remain queen.

But Giselle's plunge into darkness lands her in a strange new world - the unforgiving live-action world of modern day New York City. As the cruelty of this new place wears down the fairy-tale idealism of the once carefree princess, such as a homeless man stealing her tiara, the frightened Giselle meets divorcee Robert Philip (Patrick Dempsey), who takes her into his apartment despite believing that she is a little crazy, and he is nervous for his daughter Morgan. Robert is a divorce lawyer who doesn't believe in Giselle's gushings of happily-ever-after and true love's first kiss. The next morning he becomes aggravated when he and his daughter find Giselle has rats and other vermin cleaning their apartment and that she has constructed a dress using material cut from the curtains. Nancy (Idina Menzel), Robert's soon-to-be-fiancee, walks in to find Giselle in a towel and leaves assuming the worst. Robert takes her to his office and asks his secretary to find out where Giselle came from, which proves unsuccessful. Giselle starts to sob when she finds out that his client and her husband are getting a divorce, causing Robert's boss to angrily reprimand him. Robert takes Giselle, and they go outside the building to Central Park.

At the end of his patience, Robert gives Giselle some money and tells her to go find her prince. Giselle promptly gives the money to an old woman, which leaves Robert to shake his head in pity and join her. Robert is shocked when Giselle tells him that she and Edward only knew each other for a day, while Nancy and he have dated for five years. She starts singing "That's How You Know," and she spontaneously starts a musical production number with everyone in the park performing with her while Robert protests that he never sings or dances - ever. Giselle ends up sending Nancy a wreath of flowers as an apology from Robert along with tickets to the King and Queen's ball. Charmed, Nancy promptly accepts.

Meanwhile, Queen Narissa's henchman Nathaniel (Timothy Spall) goes after Edward and Pip, who have journeyed off to save Giselle. They stop at a motel, where Nathaniel sneaks out to give Giselle a poisoned apple, while Pip, unable to speak in this world, has a frustrating time alerting the Prince of the minion's intentions. Nathaniel tries twice to poison Giselle, only to be stopped by Pip, and Narissa becomes infuriated. Giselle stays another night in Robert's apartment and reads a book on famous women such as Rosa Parks and Marie Curie that Robert had given to Morgan as a present. Robert tells her he will help her because he doesn't believe Edward will show up. She yells at him, and becomes giddy when she finds out that she is experiencing anger for the first time. They both stare at each other for a moment and come close enough to kiss but Robert turns and bids her good night. Giselle falls into a chair, confused, realizing she is falling for him, and he does the same on his bed.

Edward finds Giselle the next morning and, at her insistence, go on a date around New York. She suggests that they go to the King and Queen's Ball that evening, and Edwards gets her to agree to leave and return with him (reluctantly) to Andalasia right after the ball. Giselle and Morgan go shopping with Robert's emergency credit card for the perfect gown.

At the ball, Nancy and Robert dance together wearing 18th century style costumes. Robert wears a blue jacket similar to what Giselle dreamed about what her true love would be wearing at the beginning of the film. Giselle and Edward arrive at the ball, and Giselle and Robert see each other. Nancy is smitten by the romantic Edward. The emcee tells everyone to switch partners for the next song, so Nancy and Edward pair off and dance with each other. Giselle and Robert dance to the song "So Close" sung by Jon McLaughlin, and Robert softly sings the lyrics to her as they dance. Giselle begins to finally realize that Robert is her true love. Nancy and Edward keep their eyes on the couple. Nancy decides to cut in and continue dancing with Robert. Giselle and Edward turn to return to Andalasia, and Giselle is visibly upset as they leave the ball. Edward leaves her by the elevators to get her wrap.

Narissa appears as the old hag. Seeing Giselle become distressed when she watches Nancy kiss Robert on the dance floor, Narissa offers her an apple that she says will make Giselle forget the whole experience. She takes it and collapses on the floor. Edward returns, and Narissa claims Giselle fainted as Robert and Nancy run to Giselle's aid. A remorseful Nathaniel appears and admits the plot that she was poisoned, sadly, with his help. He restrains Narissa with Edward's sword. If the spell isn't broken in a minute (when it will be midnight), Giselle will die.

Remembering her belief in true love's first kiss, Robert tells Edward to kiss her, only to find it doesn't work. Edward turns to Robert and realizes that his kiss has failed because Robert is her true love. Robert immediately denies this, but Nancy says it's okay and tells him to kiss her before it's too late. He does, and Giselle wakes up. Narissa breaks free from Nathaniel, seizes Edward's sword from him and then transforms into a dragon as she impales the sword onto the dance floor. Narissa declares that she will have to kill them all. She plans to start with Giselle, but Robert intervenes and is promptly seized. Narissa climbs on top of the building with Robert in hand. Giselle grabs Edward's sword from the dance floor and follows, leaving a slipper behind.

Giselle chases the dragon to the point where, thanks to help from Pip, it falls off the Woolworth Building and dissolves into glitter on the pavement. Giselle catches Robert just in time as he falls, and they kiss on the roof. Meanwhile, Edward puts the slipper on Nancy's foot, and they go back to Andalasia and get married. Robert and Giselle open up Andalasia Fashions where they are assisted by both humans and animals.

In the meantime Nathaniel becomes a successful author in the modern world writing a book entitled "My Royal Pain" and signing autographs. Similarly, Pip becomes a bestselling author in Andalasia, writing a book called "Silence Isn't Golden." The last scene shows Giselle and Robert with his daughter Morgan playing together and living happily ever after as a family in his apartment.