Winter Holliday lives for her friends, her career, the tiny town of Anneville and Christmas (not necessarily in that order). She has no place in her life for romance, no matter how much her friends, coworkers and neighbors insist otherwise. After all, the Anneville Special Events Council can hardly be expected to operate if their chairperson, top volunteer and sole member of the Decorating Committee trades in her giant tissue paper pom-poms for a chance to live out her schoolgirl fantasies with her high school crush Avery Sumner.

After leaving Anneville, Avery has found success and a steady stream of exasperation as a record producer in New York. Thanks to her capricious top star's most recent set of demands, Avery finds herself in a jam. Suddenly Anneville seems much more welcoming.

Despite an immediate attraction between Winter and Avery, a series of missed opportunities and often hilarious obstacles always seem to interfere with them doing the simplest thing in the world: fall in love.