Serendipity is a 2001 romantic comedy, starring John Cusack and Kate Beckinsale. It was written by Marc Klein and directed by Peter Chelsom. The original music score is composed by Alan Silvestri.
It is the height of christmas shopping when Jonathan Trager (John Cusack) meets Sara Thomas (Kate Beckinsale) as they both try to buy the same pair of gloves at Bloomingdale's. Two strangers amid the bustling crowd of New York City, their paths collide in the mad holiday rush and they feel a mutual attraction. Despite the fact that each of them is involved in other relationships, Jonathan and Sara go out on the town around Manhattan. They end up eating ice cream at Serendipity 3, and soon exchange goodbyes. However, both realize that they have left something at the ice cream bar, and return only to find each other again. They then head to Central Park. Upon seeing Sara's freckles, Jonathan mentions that they look like the constellation Cassiopeia. He then tells her that Cassiopeia was a very beautiful queen, but when the gods got jealous, they turned her into a constellation. At the end of the night, the two are forced to decide some kind of next step. When the smitten Jonathan suggests an exchange of phone numbers, Sara balks and proposes an idea that will allow fate to take control of their future. Sara asks Jonathan to write his name and phone number on a $5 bill, while she writes her name and number on the inside cover of a used copy of Love in the Time of Cholera. If they are meant to be together, she tells him, he will find the book and she will find the $5 bill, and they will find their way back to each other. They each get a glove from the pair both of them purchased.
Five years later, Jonathan is at an engagement party with his fiancé Halley Buchanan (Bridget Moynahan). On the same day, Sara comes home to her house to find Lars Hammond (John Corbett), a famous new age musician, proposing to her. Before getting married though, both Jonathan and Sara go to New York City to make one last attempt to find each other.
Jonathan tries to find out who the mystery girl was by using the time he had scheduled for a bachelor party with his best friend Dean Kansky (Jeremy Piven). They try to obtain her contact information by going back to Bloomingdales. They meet the same salesman (Eugene Levy), and obtain a record of Sara’s old address. (her name still was a mystery since they smeared it on the receipt). They venture to Sara’s old house where they meet a painter Mr. Mignon. who has very little recollection of Sara. Having failed at this attempt, he remembers the ice cream shop they went to and goes to check the place out again. To his dismay, it’s now a bridal shop. With this finding, Dean suggests that Jonathan quit and accept the inevitable, that they may never see each other again.
As for Sara, after receiving the proposal, she asks her best friend Eve (Molly Shannon) to go with her to around New York, where the two romantic leads almost, but not quite, meet. (One character is seen walking in to one door of a building at the exact same instant as the other character walks out of a different door in the same building, etc).
Towards the climax of the film, Jonathan receives a groom's gift from Halley—to his surprise it is the same book where Sara wrote her name and number. Jonathan then sets off and tries to find Sara, but he sees someone in her house being intimate with someone. Upon seeing this, Jonathan tells Dean that he wouldn’t have wanted to break off what they have and comes back home for the wedding. Sara, on the other hand, was surprised by Lars following her to New York. they two of them go to Central Park for stargazing. Sara sees Cassiopeia and realizes that she doesn’t want to be with Lars. She breaks it off with him but absentmindedly leaves her jacket behind.
At the wedding rehearsal, Jonathan is late due to his search for Sara. Coincidentally Eve is Halley’s college classmate and is invited to the wedding. Sara sets off home while Eve goes to the wedding. On the plane, Sara is asked if she wants a headset. To her surprise, she finds her wallet got exchanged with Eve’s. She pays the flight attendant $5 for the headset, and realizes she has the same $5 bill which Jonathan wrote on five years earlier.
Sara gets off the plane to continue the search for Jonathan. His neighbors tell her he’s getting married the same day. She rushes to the hotel only to see a man cleaning up. She is in tears until the man says the wedding was called off. Sara and Eve then get in a cab to go home, and Sara remembers the jacket she left in the park.
Jonathan, in the meantime, is wandering around Central Park. He finds Sara's jacket and uses it as a pillow as he lies down. As the first snowflake drops, the other pair of the gloves floats to him and he sees Sara. They introduce themselves to each other formally for the first time. The film concludes with Sara and Jonathan at Bloomingdales enjoying champagne on their anniversary at the same spot where they first met. Just when they are about to buy a black pair of gloves,which they do every year for luck, the same salesman appears. The film ends with the couple speaking with the salesman, once again arguing upon the dividing line in between the counter and personnel area.
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