Merry Griffin is a relationship expert whose blog, which espouses her checklist of dating rules, has a substantial following. She is parlaying that blog into her first book outlining how those rules have led to her finding her Mr. Right, fiancé Dale Westfield. In this approach to Christmas, the book is being edited by her best friend, Darlene Walters, for Littlefield, the boutique Boston publishing house where she works as a junior editor, it ready to hit the store shelves in time for next Christmas. The problem is is that Dale is not actually her Mr. Right, but someone she encountered briefly in a coffee shop as he was waiting for a blind date, he solely the inspiration for Merry's fantasy love life, something that Darlene knows, but which they learn Darlene's boss, publisher Sonia Hendricks, would have issue with in the reality being what makes Merry's manuscript stand out from the pack. As Darlene and Merry head to Darlene's hometown of Snowbridge, VT for the Christmas holidays to strategize about how they will deal with this problem which was unintentional in Merry just wanting to help people with the book, Sonia beats them to the punch when she tracks them down in Snowbridge in discovering that Dale is not real. As this book could make or break the company which also means Darlene's job, Sonia provides an ultimatum for Merry to come up with another solid book idea before she leaves town just prior to the 25th. What happens with the book and thus Merry's writing career is affected by whether she is able to demonstrate that her rules do lead to a love life, especially as they apply to herself. There are seemingly two potential men that could fill the void as that Mr. Right for Merry, each who has an issue in filling that void. The first is New York restaurateur James Smith, who happens to be Darlene's ex-boyfriend for who Darlene does not want to admit she still has feelings, despite his actions toward Merry. And the second is Darlene's brother, Adam Walters who unexpectedly came back to Snowbridge having long worked overseas doing charity aide work, the latest post in the jungles of Guatemala, while he figured out what he wanted to do with his life. His surprise visit is in part to make a geographic split with his now ex-girlfriend Julie and in part to make that declaration of his professional future: wanting to take over the family business, Walters Gift Shop and Tree Lot, he who would be the fourth generation of Walters to run it. That declaration surprises his and Darlene's parents, as he had never made any indication of wanting to do so before now. The primary issues with Adam and Merry are that they had a mutual attraction in their one and only encounter ten years ago which led to nothing for various reasons, but more importantly that Adam does not believe in any of the checklist items about which Merry writes.