Sydney Ragsdale (Thompson), recently divorced, decides to spend Christmas in a house she inherited with her young daughter. As Sydney begins to spend more time at the local bookstore, she meets a teacher, Mac (Paevey), who also fills in for the town Santa. Mac tries to make Christmas wishes come true, and this year Sydney is at the top of his ‘nice’ list. As a new opportunity with the bookstore unfolds, Mac helps Sydney open herself up to life, love, and believing in the spirit of Christmas again.

Jess Parks (Hudon) has a good job, great friends and a cool apartment in the city. She has it all, except the ability to find her perfect match that would appreciate her quirky humor and outgoing nature. The only person that ever truly understood Jess is her lifelong Best Friend Ted (Paevey). Jess and Ted grew up together as neighbors in the suburbs and were inseparable. When Ted reveals to Jess that he’s getting married and asks her to be his Best Man, or in this case Best Woman at his wedding, Jess is happy until she finds out that he’s marrying her high school rival and mean girl Kimberly Kentwood (Kruger). As Jess and Ted spend time together planning his big day, Jess realizes that her perfect match has been Ted all the time but is it too late to be his BFF bride?