Donald Hollinger is waiting in line with children and their parents to see a department store Santa Claus, where Ann is working a side job as one of his helpers. While on line, he meets a woman who just so happens to be bringing a present to her because of a good deed she did for her son Tommy. During her break, she and Donald sit down for lunch and Ann explains that three years earlier she worked at a drama teacher at a boarding school somewhere in Upstate New York. The boy whose mother brought the present for him couldn't go home to see his parents, because his mother is an actress who is on the road. Feeling bad for the boy, Ann offers to take him to the Marie house for Christmas, but the headmaster, Mr. Merriman, insists that he stay out of fear that their insurance company would cancel their coverage, should anything happen to Tommy. Instead, Ann offers to spend Christmas with him at school. As the sky grows dark, Tommy and Ann anxiously await snow, but instead the thunder brings a huge rainstorm.
The activities consist of making jelly sandwiches, playing games and decorating the school's Christmas tree. The games include checkers, basketball, chasing each other around the school, and hide-and-go seek. Another student named Roger Green, a friend of Tommy's comes over to visit and plays with both of them, but later goes home, much to Tommy's dismay. Ann decides to call Roger's family and talk them into inviting Tommy over to their house for Christmas, and he gladly accepts the offer. However she starts to feel lonely. Later while talking to her father on the phone about how his Christmas had improved, Tommy returns with a large plastic toy truck that the Green family gave him. Though the family is Jewish, they decided to throw an elaborate Christmas party just for him. Donald is impressed by her story, but she finds she has to go back to work and tend to a crying baby who's frightened over sitting on Santa's lap.
|Marlo Thomas||Ann Marie|
|Ted Bessell||Donald Hollinger|
|Lew Parker||Lou Marie|
|June Vincent||Tommy's mother|
|John Fiedler||Mr. Merriman|
|Chris Shea||Tommy Phillips|
|Gerald Michenaud||Roger Green|
|Don Keefer||Mr. Carson|
|Richard Burton (uncredited)||Kid at Boarding School|
- Episode writer Jim Brooks later wrote a thematic sequel on The Mary Tyler Moore Show - "Christmas and the Hard-Luck Kid II".
- Chris Shea, who plays Tommy, was often heard in the 1960s as the voice of Linus van Pelt in the early Peanuts specials, including A Charlie Brown Christmas. His younger siblings were also child actors of note.
- Marlo Thomas' other Christmas roles include the voice of Bertha Plummer in the 1967 animated version of Cricket on the Hearth, and the protagonist in the TV movie It Happened One Christmas.
- John Fiedler, who played the headmaster at Miss Marie's school, also appeared as Art Carney's boss in The Twilight Zone episode "Night of the Meek".