Emily is known for two things, her honest take on life in her column Everything Emily and her love of Christmas. When her boss gives her a new Christmas themed assignment, she's both intrigued and apprehensive. For the month of December, Emily has to go on twelve blind dates related to the Twelve Days of Christmas song. Her biggest question about her assignment is, how could twelve blind dates possibly be related to the song? Since the assignment isn't optional, she decides to keep an open mind, after all, how bad could twelve blind dates really be?

Emily soon finds out that there are a lot of very good-looking eligible bachelors in New York City. Despite that fact, the dates are not going as planned. As Emily writes honestly about each bad date, her readers are loving her column on a scale she never could have imagined, and her boss couldn't be happier.

Without her best friend, hot co-worker, and a mystery tree elf, she probably would have given up, but Lacie encourages her to have fun, and spending time with Matt is the best part of the terrible dates. But Emily's curiosity starts to get the better of her and she begins to realize that things are adding up when it comes to Matt.

Will Emily be able to make it through all twelve disastrous dates? And can she trust her feelings for Matt? Or will everything about this Christmas make it the worst one in history?