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.
Drew lets obese ex-wife Nicki live in his house and moves into the basement so Kellie could stay too and have his bedroom. At The Neverending Store, which replaced Winfred-Lauder, he lets Mimi be Office Manager.
When Kate announces she's getting married in a few days, upset Drew locks her in the basement while he, Lewis, and Oswald try to find dirt on her fiancé. When they find some, Kate escapes and says it doesn't matter.
To get over losing Kate, Drew sets a goal to be married by May 19. Meanwhile, Kellie struggles to replace Kate as one of the four. During a night out, Lewis goads her to steal a cutout of Jim Thome from a liquor store, and she does so and runs from the cops.
Drew is messing up dates so Kellie agrees to go along to help. When Oswald can't be her date as planned, Drew brings a very young guy from work who is taken with Kellie, but trouble ensues when he sweet-talks her.
Drew's mom likes his planned marriage date and sets him up. Things progress well and "the fur begins to fly." Oswald seems to be psychic, dreaming of a volcano eruption in next day's news. Lewis and Mimi put money down on his race pick.
Drew is seeing Dawn but discovers she's still seeing four of her exes as "just friends" with one living above the garage and each one handling an aspect of work around the house. Then she meets a guy with a sailboat sailing to Bermuda.
Drew must do an analysis/evaluation of the store's website and inventory system; clueless, he hires a high-school girl to help, then Drew and Kellie help her when her boyfriend asks another girl to prom. Steve moves in with Lewis and Oswald.
Drew takes salsa dancing lessons to prepare for his planned wedding day. Roselyn Sanchez plays his sexy dancing instructor. When Drew practices with Kellie, he has feelings for her. Kellie visits the class and sees him dancing with Roselyn.
Kellie's ex-husband Daryl comes to the Warsaw in a wheelchair with two broken legs, having fallen off her mom's roof doing free repairs. He returns her engagement ring as Drew starts having feelings for her. Drew tries to obstruct him.