Three brothers get the surprise of their lives when they are forced to work together to care for a baby over the holidays. As they slowly get the hang of things, they find themselves on unexpected journeys of self-discovery and begin to rebuild their relationships as brothers, as well as the damaged romantic and professional relationships in their respective lives…all while rediscovering their love of Christmas.
Pee-wee Herman and pals are celebrating Christmas in the Playhouse in their own creative ways: Pee-wee makes a list for Santa Claus 1.5 miles long, teaches Little Richard how to ice skate, goes for a sleigh ride with Magic Johnson, enslaves Frankie Avalon and Annette Funicello into making Christmas cards, receives a long phone call from Dinah Shore, even has more musical fun with k.d. lang, the Del Rubio Triplettes and Charo! Finally, Big Red arrives and announces that Pee-wee's Christmas list was so big, he didn't have enough presents for all the children of the world. Will Pee-wee follow his own advice and help others?
Krissy Kringle receives a delivery intended for Santa Claus. A magical book that shows if a person has been naughty or nice. She uses the book's power to find out about those around her, which leads to some very unusual and unintended results. Krissy realizes that everyone has some good and some not so good in them.
Kristin, a cynical 34-year-old, drinks a mysterious champagne on Christmas Eve and wakes up seventeen years in the past, sharing a room with her 17-year-old self. Given the chance to change the worst Christmas of her life, she attempts to fix past mistakes, only to discover surprising truths about her family that may help her mend her present-day relationships.