Winter Holliday is devoted to her friends, her career, the quaint town of Anneville, and Christmas?though not necessarily in that order. Romance is not on her agenda, no matter how much her friends, coworkers, and neighbors try to convince her otherwise. As the co-chair and vice president of the Anneville Special Events Committee, she can't imagine abandoning her duties for a fling with her high school crush, Avery Sumner.

Avery left Anneville to become a successful, albeit often frustrated, record producer in New York. When her top star makes some capricious demands, Avery finds herself back in Anneville, where life suddenly seems more inviting.

Despite an undeniable attraction between Winter and Avery, a series of missed opportunities and hilarious obstacles constantly seem to get in the way of the simplest thing in the world: falling in love.