Cusack plays Jonathan Trager, who falls for Sarah (Beckinsale) at a chance meeting at Bloomingdale's in New York City. They spend the rest of the perfect night together, as if in a fairytale. Sarah, who is naturally kooky, decides to invest in destiny by urging them to carry on with their lives. Writing her name in a book for selling to a used book shop, she urges Jon to do the same. He writes his name on the back of a five dollar bill. Of course, if one is to find the other's item, it means that they are meant to be together.

Several years later when they are both on the verge of marriage or engagement to a different person, they both look back to that one golden night spent together, imagining the what-could-have-beens.

The beginning is okay on its own, as their is an enjoyable chemistry between the two actors. Once we're back in the present time, the film never quite recovers the momentum. The movie becomes tone-deaf and hard to buy into.