An unemployed art teacher accepts a job with the Santa Squad to help lift the spirits of a wealthy widower Gordon (Aaron Ashmore) and his two adorable daughters. As she helps the broken family rediscover the magic of Christmas, she finds something she didn't expect: True love.
Temporarily unemployed, Allie, a middle school art teacher, is looking for a job for the Christmas holidays. Her friend Tony, who works at a community center mostly shut down for the holidays, lets her know about a job posted on the center's bulletin board for people to be part of The Santa Squad, which does personal services all things related to Christmas. Showing her prowess to Mr. Karl who does the hiring, she is assigned to work on the important "church" file, which she learns does not refer to a religious institution upon her arrival at her work-site, but rather the extremely wealthy Church family headed by widowed businessman Gordon Church. Her responsibilities will be to help prepare the Church mansion for Christmas to very detailed specifications, the minimalist elegance of those specifications seemingly dictated by Gordon's girlfriend, Kimmee. Through those responsibilities, Allie can see that Gordon's two adolescent daughters, Rose and Iris, are not considered inherently in what is happening for Christmas, which is probably an indication of the emotional neglect they face from their father, in his preoccupation with business, and Kimmee in general, although she can see that Gordon does love them. Although not part of her responsibilities, Allie, in her natural caring attitude, tries to bring Rose and Allie into the goings-on of Christmas in their house, and in the process get them out of their respective shells, which largely hide their true character from their father. Allie's actions have unintended consequences in many respects.