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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 wasnt 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 cant 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 Bloomingdales 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 others last name or telephone number as they part company. One of Saras 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 Jonathans mind. Sara too is thinking about Jonathan rather than Lars. As Jonathans 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 Jonathans scheduled wedding?
John Cusack
Jonathan Trager
Kate Beckinsale
Sara Thomas
Jeremy Piven
Dean Kansky
Bridget Moynahan
Halley Buchanan
Eugene Levy
Bloomingdale's Salesman
Lilli Lavine
Bloomingdale's Stock Girl
Michael Guarino Jr.
Customer At Bloomingdale's
Abdul Alshawish
Customer At Bloomingdale's
Stephen Bruce
Host At Serendipity
David Sparrow
Josh's Dad
Ann Talman
Bloomingdale's Saleswoman #1
Crystal Bock
Bloomingdale's Saleswoman #2
Gary Gerbrandt
Josh
Kate Blumberg
Courtney
Ron Payne
Louis Trager
Marcia Bennett
Mrs. Trager
Victor A. Young
Mr. Buchanan
Eve Crawford
Mrs. Buchanan
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