When Tracy and his wife Alicia attend a parent-teacher conference, they find that while their 13 year-old son Derrick receives high marks in his studies, he is lacking in social skills. To improve the situation, Tracy makes it his mission to help Derrick woo his dream girl Simone until he and his 7-year-old son Jimmy see her in the flesh and determine that she is out of Derrick's league. Meanwhile, Tracy is frustrated by the mechanics at his shop when they do work for a customer who prefers barter to cash payment.

A frightened Jimmy causes a scene when his mother Alicia takes him to the doctor's office for a routine physical, prompting her to give Tracy the task of accompanying their son to his rescheduled appointment. When Tracy reveals his own fear of going to the doctor, his mechanics Spoon and Bernard offer encouragement and therapy--based on their own phobias--to help him and Jimmy overcome their fears.

While reading through Jimmy's letter to Santa - which includes a detailed confession of how he destroyed his dad's special edition ""Planet of the Apes"" DVD - Tracy discovers that his son lied to him and decides to teach him a Christmas lesson with the help of Old St. Nick. However, when Santa doesn't cooperate, Tracy decides to get a little physical and leaves Jimmy believing that Christmas is ruined. Meanwhile, Alicia attempts to discover what Derek wants for the holidays, and Spoon, Bernard and Freddie attempt to write the perfect black Christmas carol.

Tracy uses his 15th wedding anniversary as second chance to properly propose to Alicia, planning an elegant dinner as the perfect setting to drop down on one knee and present her with a new engagement ring. However, his magical night hangs in jeopardy when the couple is unable to find a babysitter -- prompting Tracy to put his faith in Derek to take charge and watch the house and Jimmy

Derrick and Jimmy volunteer in a church program that takes food to the elderly and they find stuff on the street to bring in the Mitchell house hold; Tracy goes to jury duty; Spoon and Bernard fight for second-in-command at the shop while Freddie prepares for his annual bike tour.