Sophie Jones has had more than her share of misfortune. Orphaned at a young age by a fatal car accident, her life has been the definition of tragedy, and every time she tries to move forward, her past drags her back. Her one consolation is discovering she's not alone when she whips up a batch of Misfortune Cookies that become a surprise hit with customers at her chocolate shop. Dipped in bitter chocolate, people delight in Sophie's unique handwritten fortunes far more than the unpalatable taste, even if reading, "Is it love or pity? Try not to dwell on it." isn't exactly the kind of thing to lift one's spirits.

It's not that Sophie is depressed, she's just a realist, and her luck seems true to rotten form when Garrett Black walks into her shop as a birthday surprise. He broke off their engagement with no explanation and disappeared. Now he wants to explain, but Sophie's far too wise to open herself up to him again. When he reacts with surprise and dismay to her Misfortune Cookies, Sophie sees the perfect opportunity to dodge the conversation.

She proposes Garrett take out a want ad in the local paper seeking sustainable happiness. When he gets a hundred responses she deems acceptable, she'll go out on one last date and hear him out. Sophie knows he has no chance of winning, but fate may have other ideas.