After Drew is released from the mental ward, he sees Nicki at the Warsaw and they get married but no one else knows. Meanwhile, Kate discovers she has feelings for Drew and tells Lewis and Oswald. Kate declares her love for Drew.
Drew is stretching himself thin trying to keep Kate and Nicki from knowing he is married to both of them. He is telling Kate that Nicki's on drugs and he tells Nicki that Kate is delusional and thinks she and he are married. Mimi meddles.
The new boss makes his appearance and he and Drew hit it off. He's such a good egg they throw a Halloween party but things go terribly wrong for the boss. Can Drew orchestrate the moment to become boss a la Weekend at Bernie's?
Drew's parents are visiting and his mom tells Mimi that her husband isn't satisfying her in the bedroom. Mimi convinces Drew to tell him. Lewis and Oswald build a battle robot for a competition at the Warsaw. First design does poorly.
Drew comes to in an animal shelter with John Ratzenberger having no idea how he got there. He begins to unravel how it happened, remembering a horrible event that made him want to end it all. Did he really share a night with Mimi?
The new boss at Winfred-Lauder, played by Wanda Sykes, has a mandate to trim the staff and treats everyone harshly. But she's sweet on Drew. He spends the night with her but she thinks it is because he was bribed by the staff to do so.
Drew feels like a kept man when his girlfriend/boss has him run many personal errands. When driving her poodle, Mr. Laffoon, to a dog groomer in her 'Vette, he races Mimi in her new Mustang, hoping his girlfriend Christine doesn't find out.
Drew inadvertently demonstrates to Winfred-Lauder execs he is no longer needed and so is fired. Needing income, he rents a room to a gay couple played by Adam West and Max Gail. Lewis and Oswald build a home but need clowns to finish it.
Bothered that Kate is not sharing about her life with him, Drew gets a transfer as security guard near her job at the Rock and Roll Hall of Fame at the Elvis exhibit. When his girlfriend, played by Wanda Sykes, finds out, she's not happy.
Mimi and Steve enter King Gus in Winfred-Louder's baby pageant. Drew then thinks it's time to ask Mimi to let him babysit Gus when Mimi and Steve go out for the day. But Drew accidentally teaches Gus certain inappropriate gestures, so he must try to get Gus to stop doing them before the pageant. Meanwhile, Oswald recruits his girlfriend's nephew for the pageant and tries to improve his chances by teaching him a magic act.
Drew angers neighborhood dogs when he runs one off. Because the rest of the gang aren't coming by, he sends out word there's an emergency. They arrive to find a pack of menacing dogs are blocking exit. Has Lewis' famous bucket-head scene.
The new owner of Winfred-Louder gives it to his spoiled 19-year-old daughter and warns Drew that if she fails at running it, he'll lose his promotion. She repays him for intervening in her in-store romance by moving him to the loading dock.
Drew persuades Lord Mercer to re-hire his daughter Milan as president of Winfred-Louder. She holds an in-store rave that seriously boosts sales but he still isn't pleased. Lewis eats the human liver that Oswald brought home for medical classes.
Because of his support in her struggle to manage Winfred-Louder, Milan invites Drew to her birthday party with supermodels in Spain. When security lines delay him from catching his flight, he tries to bypass them and is pulled aside.
Steve is uncharacteristically violent, assaulting a man at his son's daycare center and one at Winfred-Louder's cosmetic counter where Drew got him a job. Drew is convinced that Steve's aggression comes from jealousy of him.
Milan, the manager of Winfred-Lauder, sets up Drew with her mom (played by Julia Duffy from "Newhart"). Although she is wealthy, she is attracted to the normality of Drew's life but has a difficult time coping with middle class life.
Lewis wants to bring a date to the wedding of a former girlfriend who told him he would always be alone. The gang tries to help him but each fail. His mom arrives and reveals he has a 162 IQ but doesn't know it. Then he tries a Mensa party.
Drew's ex-wife Nicki re-connects with Drew but she has re-gained the weight because of her anger issues. Winfred-Lauder has been nearly ruined by embezzlement so Drew suffers the humiliation of working the men's underwear counter.