Jennifer Cullen (Brooke Burns) is a single, working mom who has become somewhat of a Scrooge when it comes to the Holiday season. Even her six-year-old son Brian is having trouble believing in Santa Claus. When Jen’s Uncle Ralph (Henry Winkler), a retired police officer, comes to visit for Christmas, he brings along a new friend, a nomad and Jack-of-all-trades named Morgan Derby (Warren Christie). The two met on a flight, and Morgan’s plans to continue on to Denver are cancelled when he finds out the city is completely snowed in. Jen is wary of the stranger, but at Ralph’s request, agrees to let him stay the night. She warms up to Morgan, especially when she sees how he interacts with Brian. Uncle Ralph approves of Morgan, too, but Jen’s boyfriend Richard isn’t nearly as receptive. Meanwhile, Morgan has started to really like Jen, but if she can’t manage to make Christmas about anything more than business, Morgan will be on his way to Denver, and she’ll have missed the opportunity that was right in front of her. Uncle Ralph has done what he can to keep Morgan around, but it’s going to take something more than that to get him penciled into Jen’s long-term plans. Jen just needs to learn “how to do Christmas,” and it turns out Morgan is the perfect one to teach her.
Christie Reynolds (Krakow) and Penny Miller (Frigon) have been archrivals ever since a memorable fight over a coveted Christmas recital solo in elementary school. Now adults, they work side-by-side at the same school where they still constantly compete over everything. As the holiday season approaches, the entire school is getting into the spirit with the annual fundraising festival, which will feature an exciting new event—a teacher Christmas Cookie Bake-Off, judged by a tough five-star chef, Chef Krueger (Thicke). Penny and Christie immediately clash over the contest, both wanting to beat the other to win the grand prize, a free class trip. Christie, however, is hopeless in the kitchen, despite help from her mom, Bev (Laura Soltis, "Hiccups"). She doesn't think she has a chance—until she meets James, a new student's handsome and sweet single dad. In addition to running a charitable shelter, James is also an excellent cook. As both Christie and Penny vie for James's attention in yet another aggressive battle, Christie starts to tutor his precious, kindhearted daughter Lily (Genae Charpentier, "Girl Vs. Monster") and gets to know James outside of school. As their relationship starts to deepen, and James' baking expertise guides Christie's cookie creations, Christie’s competitive edge starts to soften. But at the final bake-off challenge, James is finally caught in the middle of Christie and Penny’s petty feud, and Christie comes to realize life’s most rewarding prizes don’t come with a trophy.
