A couple search for each other years after the night they first met, fell in love, and separated, convinced that one day they'd end up together.
Jonathan Trager and Sara Thomas met while shopping for gloves in New York. Though buying for their respective lovers, the magic was right and a night of Christmas shopping turned into romance. Jon wanted to explore things further but Sara wasn't sure their love was meant to be. They decided to test fate by splitting up and seeing if destiny brought them back together... Many years later, having lost each other that night, both are engaged to be married. Still, neither can shake the need to give fate one last chance to reunite them. Jon enlists the help of his best man to track down the girl he can't forget starting at the store where they met. Sara asks her new age musician fiance for a break before the wedding and, with her best friend in town, flies from California to New York hoping destiny will bring her soulmate back. Near-misses and classic Shakespearean confusion bring the two close to meeting a number of times but fate will have the final word on whether it was meant to be.—Lordship <[email protected]>
While each grabbing for the last pair of black cashmere gloves at Bloomingdale's in New York, Sara Thomas and Jonathan Trager meet. Despite each being in a relationship with other people at the time, they spend an amazing afternoon together. Jonathan wants her contact information "just in case", but Sara, a fatalist, plays games of fate with Jonathan to determine if they are indeed meant to be together now or in the future. At the end of the day, the two only have a few pieces of information about the other, which does not include the other's last name or telephone number as they part company. One of Sara's last games of fate that day has each leaving a identifier to the other (Jonathan and Sara scrawl their full name and telephone number on a $5 bill and a used book, respectively), which if each comes into the possession of the other by happenstance, Sara believes they are meant to be together. A few years later, Jonathan is engaged and soon to be married to a woman named Halley. Concurrently, Sara, now living in San Francisco, has too just gotten engaged to Lars, a new ageist musician. However, the thought of Sara is foremost in Jonathan's mind. Sara too is thinking about Jonathan rather than Lars. As Jonathan's wedding day approaches, Jonathan, with his best friend Dean at his side, uses a methodical approach to locate Sara. On the other hand, Sara, with her best friend Eve at her side, uses a more fatalistic approach to finding Jonathan. Will either of their search efforts result in success, especially before Jonathan's scheduled wedding?—Huggo
Jonathan is shopping at Bloomingdales for the perfect Christmas gift. Ironically, so is Sara. They both grab the last pair of black gloves, forcing them to look up from the chaos. Meeting by chance, they have an incredible night out together. Realizing they're both in committed relationships, they part ways... but not before giving fate a chance to prove they're truly meant to be together. Years go by and both Jonathan and Sara have found love with other people. While planning their weddings, the universe keeps sending them signs reminding each of them about that one night in New York. This leaves both of them questioning their current relationships. The curiosity of "what might have been" has both Sara and Jonathan searching for answers. No matter how hard they look or try to figure things out for themselves, the ultimate decision is left in fates hands.—Carrie DeCosta
Jonathan Tragger meets Sara Thomas by chance in the Christmas eve, in Bloomingdale's, both trying to buy the unique pair of black gloves available for sale. They decide to go to the cafeteria Serendipity and Jonathan asks for her name and phone. Sara decides to write it in a book, and his on a five dollars bill. She gives the bill to a newspaperman and she says that she would sell the book in a New York used books store. She states that if destiny wants them two together, Jonathan will get that book back. Or she will receive that bill again. From this day on, Jonathan will 'chase' Sara's book trying to reach his lost love.—Claudio Carvalho, Rio de Janeiro, Brazil
During the Christmas shopping season in New York City, Jonathan Trager (John Cusack) meets Sara Thomas (Kate Beckinsale) as they both try to buy the same pair of black cashmere gloves at Bloomingdale's. They feel a mutual attraction, and despite the fact that each is involved in other relationships, they end up eating ice cream at Serendipity together, 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.
Considering this to be a stroke of fate, Jonathan and Sara decide to go 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 writes hers down, but it flies away with the wind. Wanting fate to work things out, 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 copy of Love in the Time of Cholera. If they are meant to be together, he will find the book and she will find the $5 bill, and they will find their way back to each other.
Jonathan is not satisfied with this, so they go into a hotel with 28 floors and enter into different elevators to see if they both choose the same floor. They each take a single glove from the pair they purchased. They both press floor 23, but a child gets on the elevator with Jonathan and presses all the buttons, so it is too late by the time he reaches floor 23. The two believe they've lost each other forever.
Several years later, Jonathan is at an engagement party with his fiance Halley Buchanan (Bridget Moynahan). On the same day, Sara comes home to her house to find Lars Hammond (John Corbett), a famous musician, proposing to her. As their wedding dates approach, each find themselves with a case of cold feet, and decide to return to New York in an attempt to find each other again.
Jonathan and his best friend Dean Kansky (Jeremy Piven) return to Bloomingdale's in an attempt to find Sara. They meet the same salesman (Eugene Levy) and eventually end up with only an address. They meet a painter who recalls that she lived there for a short time after being referred by a placement company, which he identifies as being located in a shop next to Serendipity. Jonathan and Dean follow the lead to find that the agency has moved, and its former location is now a bridal shop. Jonathan takes this as a sign that he is supposed to stop looking for Sara and get married to Halley.
Sara takes her best friend Eve (Molly Shannon) with her to New York, where she visits the locations of her date, hoping that fate will bring back Jonathan. At the Waldorf Astoria, Eve bumps into an old friend--Halley--who is there to get married the next day. Halley invites Eve and Sara to the wedding without anyone realizing the groom is Jonathan. Failing in their search, Sara and Eve console themselves with a coffee at Serendipity. Eve is handed the $5 bill as change.The day before the big event, Halley hands Jonathan a copy of Love in the Time of Cholera as a gift, having noticed him picking up the book every time they're in a bookstore. It is the copy that Sara had written in, and he immediately sets off to find her. He sees people in her house being intimate, when it's actually Sara's sister and her boyfriend. Jonathan then comes back home for the wedding.
Sara decides not to attend the wedding and starts to return home. She goes to the Waldorf to retrieve her belongings, 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. On the plane the next day, Sara finds that her wallet got exchanged with Eve's. She realizes she has the same $5 bill which Jonathan wrote on several years earlier and gets off the plane to search for him. His neighbors tell her he's getting married the same day. She rushes to the hotel, only to see a man, apparently cleaning up at the end of the ceremony. She is in tears until the man says the wedding was called off. Sara later remembers the jacket she left in the park.
Jonathan is wandering around Central Park. He finds Sara's jacket and uses it as a pillow to lie down. As the first snowflake drops, he sees Sara. They introduce themselves to each other formally for the first time. The film concludes with Sara and Jonathan at Bloomingdale's, enjoying champagne on their anniversary at the same spot where they first met.
