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The movie opens in Bloomingdales as we follow the path of a pair of cashmere gloves carried from an upstairs office down to the sales counter. The second it is put on the sales rack it is snatched by Jon (John Cusak) and Sara (Kate Beckinsale), each grabbing one of the two gloves. It's just a few days before Christmas and they both want it for their boyfriend and girlfriend. Eventually Sara buys it and the two of them have an instant connection. Sara offers to buy Jon a cup of hot chocolate and she takes him to a coffee shop named SERENDIPITY. Sara loves the word Serendipity and everything it implies. She really believes in fortunate accidents.
Afterwards they go their separate ways but knowing that they hit it off real well. A few minutes later Jon realizes that he left his scarf at the shop and when he goes back he finds Sara there who left her package.
Sara knows this is fate and the two spend a wonderful evening walking around the city. Jon wants to see her again but she is really hooked on this whole fate thing. She writes her name and number in a book and says she will sell it to a used book store. If they are meant to be together, he will find the book. She also has Jon write his name and number on a $5 bill and makes a purchase with it at a news stand. Fate will bring that bill back to her. She gives Jon one of the gloves and she keeps the other. Someday, maybe they will have a pair again. One final test is the elevators at the Waldorf Astoria Hotel. They both are in the lobby and they will take separate elevators and choose a floor at random. Turns out they both choose floor #23 but Jon's elevator is interrupted by an annoying little kid who presses all the buttons. By the time he makes it to that floor, Sara has already left.
It's now a couple years later and Jon's best friend Dean (Jeremy Piven) is giving a toast at a dinner. He is to be Jon's best man at the wedding to take place a few days from now. We finally see his fiancé and it isn't Sara. It is Halley (Bridget Moynahan). Halley doesn't suspect anything even though Jon has secretly been searching for Sara ever since she left. He has scoured every used book store in the city but has finally given up and will marry Halley.
Meanwhile, on the other side of the country is Sara, now a counselor in San Francisco. She is also engaged and has never stopped thinking about Jon. Her fiancé is a New Age music star named Lars (John Corbett).
Just days before his wedding, all Jon can think about now is Sara. Everything he sees reminds him of her. He and his friend Dean make one last attempt to find her using credit card reciepts, housing offices and even talking to old roomates of hers. No luck though, they need to know her last name. On the night before his wedding, Halley gives him a present. She tells him that ever since she has known him he has been looking for this book so she bought him a copy. It's the same title as the one Sara wrote in and when he opens it up... there is her name. They track down where Sara is living and head to San Francisco. When they get to her house they see in her window a girl who looks like Sara, making love to someone.
Turns out it is actually a friend of Sara's who is just house-sitting. Jon decides it's over and heads back to New York.
At the same time, Sara just can't get Jon out of her mind and invites her best friend Eve (Molly Shannon), to come with her to New York to help her try to track him down. After many close encounters including meeting one of Eve's old friends who just happens to be Halley, they still can't find Jon. Sara gives up and boards a plane to back to California. The plane is delayed so the flight attendants decide to show the movie while they're on the ground. To purchase headphones, Sara hands the attendant a $5 and then notices Jon's name and number on it.
She rushes out of the plane, makes a quick call and goes to Jon's apartment. The caretaker of the building tells her that she is late for Jon's wedding at the Waldorf Astoria. She grabs a cab and speeds to the hotel. When she gets there she sees the custodian taking down the wedding decorations and chairs. "Is it over?" she asks. He says that yeah, it's over. As she starts walking away he says that it's over because the groom called the wedding off at the last minute. She walks around downtown and accidentally leaves her coat on a park bench out front of the skating rink they were at years earlier.
We next see Jon walking around downtown New York. He passes by the skating rink and sits on a bench to ponder what he is going to do. He sees the coat laying there and picks it up and heads into the middle of the rink and lays down, using the coat for a pillow. He is holding the one glove and just staring up into the star-filled sky.
It starts snowing and suddenly in the snowflakes, Jon sees a glove floating down. He grabs it, sits up and looks around.
There standing at the edge of the rink is Sara. They have an emotional embrace at center of the rink.
The final scene shows them drinking champagne back at the counter where they first met.
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