During the bustling Christmas season in New York City, Jonathan Trager and Sara Thomas meet by chance while shopping for gloves at Bloomingdale's. Despite both being in relationships, they feel an undeniable attraction and spend the evening together. Sara, a firm believer in fate, tests their connection by asking Jonathan to write his name and number on a $5 bill and then spends it. She, in turn, writes her contact information in a book, which she plans to sell to a secondhand store. If they are truly meant to be, Sara believes the items will find their way back to each other.

Years later, both have moved on with their lives but can't shake the memory of their brief encounter. Jonathan is on the verge of marrying another woman, while Sara is also preparing for marriage. Influenced by a lingering sense of destiny, they embark on separate quests to find each other using the clues from their past meeting. Jonathan searches for the elusive book, while Sara hunts for the $5 bill, both hoping that fate will bring them together again.