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.