Jack Blanchard is just another self-pitying soul, drifting through life, not especially miserable, not especially content. Riddled by anxieties, he leads a solitary lifestyle, claiming a kind of self-deluded satisfaction with his station while presuming no one can tolerate him.

Now, however, he is facing the most terrifying prospect of his life: a destination wedding where he knows almost no one while being absolutely confident no one wants him there. The destination: the quaint college town of Williamsburg where Jack attended university and the only place he actually felt at peace with the world

Very quickly, Jack will start to find his world view challenged thanks to a chance encounter with a fellow guest at the wedding: a striking, acerbic, and witty sister of the bride named Jessica. Surprisingly, Jessica tolerates Jack's presence sometimes. Unsurprisingly, she is engaged and dismisses most of his life philosophy as utter nonsense.

A fascinating woman with a strange appreciation for Carl Jung, Jessica compels Jack to serve as a kind of tour guide while she explores every aspect of the town and ignores the fact that Jack is falling for her.