Throughout the Christmas season in New York City, Jonathan Trager satisfies Sara Thomas trying to purchase the same set of black cashmere gloves at Bloomingdale’s. They feel a mutual attraction, and regardless of the fact that each is associated with other relationships, they end up eating ice cream at Serendipity 3 together, and soon exchange bye-byes. Both realise that they have left something at the ice cream bar, and return only to discover each other once again.

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Considering this to be a stroke of fate, Jonathan and Sara choose to head out on the town together, and ice skate on the Wollman Rink at Central Park. Jonathan teaches Sara about Cassiopeia, saying that the freckles on Sara’s arm match the pattern of the Cassiopeia constellation. At the end of the night, the smitten Jonathan suggests an exchange of phone numbers. Sara composes hers down, but it flies away with the wind. Desiring fate to work things out, Sara asks Jonathan to compose his name and telephone number on a $5 costs, while she composes her name and number on the within cover of a copy of Love in the Time of Cholera. If they are implied to be together, he will discover the book and she will discover the $5 costs, and they will discover their method back to each other. Jonathan is not pleased with this so they enter into a hotel with 28 floorings and get in into various elevators to see if they both pick the exact same flooring. They each take a single glove from the set they bought, and each of them selects flooring 23. A little kid gets on the elevator with Jonathan and presses the buttons, for essentially every flooring, triggering Jonathan to get here on floor 23 seconds after a rather disappointed looking Sara vanishes inside an elevator. The two believe they’ve lost each other for ever.

Several years later on, Jonathan is at an engagement party with his fiancée Halley Buchanan. On the same day Sara comes house to find her partner Lars Hammond, a famous artist, proposing to her. As their wedding dates approach, each find themselves with a case of cold feet, and decide to go back to New York in an effort to find each other once again.

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Jonathan returns to Bloomingdale’s in an effort to discover Sara. He meets a salesperson and eventually, with the help of his friend Dean Kansky and the salesperson, Jonathan ends up with only an address. After additional research study, Jonathan and Dean meet an artist who recalls that Sara dealt with him for a brief time after being referred by a positioning company, which he identifies as being found in a store next to Serendipity 3. Jonathan and Dean follow the cause discover that the company has actually moved and its former location is now a bridal store. Jonathan takes this as an indication that he is expected to stop looking for Sara, and get married to Halley.

Sara takes her friend Eve with her to New York, where she checks out the locations of her date, hoping that fate will restore Jonathan. Celebrating Eve’s birthday, Sara and Eve check out Serendipity. Eve is handed a $5 costs as modification. At the Waldorf Astoria, Eve run into an old friend– Halley– who is there to obtain wed the next day. Halley welcomes Eve and Sara to the wedding without anyone realizing the groom is Jonathan. Sara goes back to her hotel room, where she finds Lars, who followed her to New York. While with Lars, she sees Cassiopeia in the sky, and breaks her engagement with him.

The night prior to their wedding event, Halley hands Jonathan a copy of Love in the Time of Cholera as a gift, having observed him getting the book whenever they’re in a bookstore. It is the copy that Sara had written in, and he right away triggers to discover her. When he gets to her house, he sees someone inside making love. Thinking it is her and now feeling foolish and defeated returns home for his own wedding.

Sara chooses not to go to the wedding event, and begins her journey home. On the airplane, she discovers that her wallet has been incorrectly changed with Eve’s. As she reaches inside to spend for a beverage she understands the $5 bill she hands to the flight attendant is the one which Jonathan composed on a number of years previously. She gets off the airplane to look for him. His neighbours tell her he’s getting married the same day. She hurries to the hotel, only to see a guy, obviously cleaning up residues of the end of the event. She remains in tears and relying on leave, when the guy tidying up remarks, how unfortunate that the wedding was cancelled. She leaves and later on remembers she left her coat in the park.

Jonathan, while roaming around Central Park, discovers Sara’s coat on a park bench and wanders out onto what was the ice skating rink when they first met, and now is a roller snowboarding rink throughout the warmer weather where they invested that very first day together. He lies down on the rink surface and utilizes the coat as a pillow. As the first snowflake drops, he sees Sara. They present themselves to each other officially for the very first time. The film concludes with Sara and Jonathan at Bloomingdale’s, taking pleasure in champagne on their anniversary at the exact same spot where they first satisfied

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