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 tow, 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.
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?
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.
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.
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.
- Can once in a lifetime happen twice?
When Jonathan and Sara meet for the first time, there's a definite attraction between the two of them, but they're both attached. Sara is a big believer in "meant to be", and when she gives Jonathan her phone number only to have the wind blow the number from his hand, she sees this as a sign that the two of them are not meant to be together - at least not right now.
Years pass, and now Jonathan (John Cusack) is engaged to marry someone else. He loves his fiancee, but suddenly he's thinking a lot about Sara. Across the country, Sara (Kate Beckinsale) has also just gotten engaged, but she's starting to wonder about Jonathan. They're both starting to wonder what might have been.
The two launch a search to find one another, armed with very little information about the other - they don't even know each other's last name, let alone an address or phone number.
The plot twists as the two try to find one another in New York City, seemingly against all odds, although they're closer than either of them knows. Their paths ALMOST cross several times, but not quite. Will they ever find each other? Will they find each other again before Jonathan marries Halley? Or will it be too late?