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.
Oswald fails the Nurse exam again and needs a job. One has opened up at Drew's work but Drew doesn't think Oswald can do the job. When Oswald is offended Drew gets him the job and Oswald trains well. Mimi vs Traylor fighting escalates.
After the gang buys a trip to Florida, Drew decides he needs to attend a computer-programming class to earn better money. He changes his mind and tells his bosses his grandma died so he can go, but then he's sick the whole time.
At karaoke night at the Warsaw, Kellie tries to sing but needs Drew's help. They are told of a karaoke contest with $1,000 and an Olympic gold medal for winning. Drew and Kellie prepare to compete but for some reason Drew pushes too hard.
Drew bumps into his former pastor and his daughter Elaine at the Warsaw. Drew asks her out and she accepts. Drew finds out she's gay and she reveals she wants him to play along to quiet her parents. Then they start vying for the same woman.
Kellie says her "birthday is next week and I have nothing to be happy about." Lewis and Oswald have termites and give Drew an invitation to a mountain condo so they can stay at his house. At the condo when staff hits on Kellie, trouble.
Evan gives Drew an old rundown Rolls Royce, but Drew can't afford to restore it so he gives it to Lewis. But Lewis goes power-mad and thinks himself above the "mortals," so Drew must somehow take back the Rolls.
When Drew throws out some mugs given to him by Lewis and Oswald, it sets off a prank war that includes moved furniture, painted bar stools and ends in an unneeded colonoscopy, which costs Drew a shot with his new doctor.