Drew decides to take night school classes to pursue a master's degree after a young man he was mentoring suddenly receives an executive position at Winfred-Louder. When his statistics professor recommends that the students find study partners, Drew pairs with Celia, a 62-year-old woman who is the only other ""old person"" in the class. They have a good time hanging out at Drew's house after a study session, and soon realize that they are attracted to each other. Celia stays the night, although they do not have sex. Drew's friends mock him after learning of the age difference, but he insists that he really likes Celia. He is puzzled when Celia ignores him in class and says that she doesn't want to see him anymore. Drew shows up at her favorite bingo parlor, and Celia explains that she dumped him because she thought he would eventually become embarrassed by her. Drew proves himself by taking over for the bingo caller and publicly announcing his feelings. Celia agrees to date him.

Drew's parents arrive unexpectedly for Christmas. They assume that Celia is his maid, and he is reluctant to reveal the true nature of their relationship. Celia's son, Chip, shows up at her house in the middle of the night. He has come to visit for the holidays. When Drew comes downstairs in Celia's bathrobe and tries to make conversation, Chip punches him in the face. Drew's parents are horrified when he finally tells them that he and Celia are dating. Celia and Chip come over to Drew's house to have dinner with Drew's parents and Steve. It proves to be a disaster. Meanwhile, Lewis and Oswald agree to help Mimi with door-to-door Christmas tree sales after she fires an associate. Kate comes along to help supervise the guys. They make very few sales (aside from Wick buying two trees to get them to go away), and accumulate several fines.

Celia returns from an out-of-town trip and learns about Drew's fight with Winfred-Louder. She offers her support. The store recruits Mimi to try to drive Drew out of the house. She points blinding lights at the house and constantly blasts ""Panama"" by Van Halen. Larry and Chuck later tell Drew that Winfred-Louder's investors gave up and backed out of the mall project. The store decides to rent all of the houses it had purchased to employees. After learning that Mimi continued to torment him for days after he had already won the battle, Drew gets revenge by tricking her into sending her outfits to a fake dry cleaner, who ruins them. Drew asks Celia to move in with him. Lewis, Oswald and Kate become creeped out by Drew's relationship with Celia, as they feel that they are acting like mother and son. The store's contractor reassembles Drew's house in an improper fashion, causing the kitchen to slope. Wick refuses to pay for the repairs, so Drew has to contact a lawyer. Drew and