It's the winter of 1990 and Jonathan Trager (JOHN CUSACK) and Sara Thomas (KATE BECKINSALE) are doing their holiday shopping in New York City. They meet when both go for the same pair of gloves and find themselves immediately smitten with each other.
After spending the evening wandering around Manhattan, Jonathan would like to continue seeing her. Sara, on the other hand, wants to see if fate has them destined to be together and so runs a series of small tests that will prove whether or not the two are meant to be a couple. Unfortunately, the tests fail, leaving Jonathan not even knowing Sara's name or address and the two going their separate ways.
A few years later, Jonathan is a TV producer still in New York, engaged to marry Halley (BRIDGET MOYNAHAN) in just a few days. Sara, on the other hand, is now a counselor living in San Francisco with her new fiancé, Lars (JOHN CORBETT), a musician.
Despite the distance and the passing years, however, the two have not been able to shake the feeling that they may have missed out on the perfect person for them. Accordingly, Jonathan - with the aid of his best man, Dean (JEREMY PIVEN), and a reluctant Bloomingdale's salesman (EUGENE LEVY) - and Sara - with her best friend, Eve (MOLLY SHANNON) - set out to track down the other and see if their feelings are legitimate before it's too late to turn back.