Drew suffers a constant series of mishaps at work, from dumpsters blocking his parking space to broken chairs and a seemingly endless supply of faulty pencil points. He begins to suspect that someone is out to get him, but his friends feel that he is just paranoid. However, Chuck shows Drew a videotape in which three men sit around discussing how much they hate Drew, and all the things they have done to make him miserable for the last decade. The men indicate that they will pull their ultimate prank the next day. When they cannot be found at work, Drew evacuates the store. The men then show up, and Drew demands to know why they dislike him. One of them says that Drew caused him to lose his fiancée by getting jelly on his collar; she mistook it for lipstick and dumped him. Drew got the second man in trouble by repeating his insults about the boss when he was in earshot, and the third guy didn't like being reported for drinking at work. The guys decide that they are tired of hara

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.

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

Drew has trouble getting another date with Tracy because Lewis and Oswald are keeping her booked. He meets one of Winfred-Louder's catalog models, who complains that she and her model friends haven't been invited to any parties while in Cleveland. Drew follows Kate's suggestion by organizing a slumber party at his house for the models. Drew plans to sneak out for a date with Tracy during the party. Unfortunately, a blizzard keeps the models away and prevents Drew from going on the date. Lewis and Oswald learn of his plans and vow revenge. They suggest that the guys at the party learn swing dancing to impress the ladies, and proceed to injure Drew as many times as possible. They decide to set aside all rules or attempts to act gentlemanly as they pursue Tracy. Mimi holds a women in business seminar, where Kate sucks up to Mrs. Louder to get her job back. Steve also attends, explaining that the fact that he dresses as a woman means that he faces the same disadvantages as women i

Drew's dog Speedy disappears from DrugCo while taking part in clinical trials for a new canine medication, so the gang breaks into the facility to find him.