Deacon gets a sandwich named after him at Cooper's, infuriating Doug. Holly (Nicole Sullivan) announces she is moving away with her boyfriend, but Carrie is not fond of the idea and Arthur cannot seem to say good-bye.
Spence wants to go to a Fantasy Fest with Lou Ferrigno but dumps him after Adam West agrees to go to the Fest with Spence. Meanwhile Doug frequently visits a very pretty hairdresser.
Doug and Carrie's weekend at a quaint bed and breakfast turns out to be less than desirable. Worse, they do not feel comfortable about leaving because they are the only people at the inn for the entire weekend.
Doug and Carrie try to get Deacon and Kelly to buy the house next to them, but a couple with eight kids moves in instead. Meanwhile Danny and Spence compete over a girl from Albania named Zana.
Carrie goes away with Arthur to visit her mother's grave and finds out she's not who she thinks she is; Doug and Ray spend the weekend trying to pick up girls, attempting to outdo each other in a nightclub.
After Carrie is told she might not get a promotion because of her accent she seeks Spence for help. Doug's mom comes to visit and after seeing her play poker, Doug takes her to Vegas to hustle some people out of their money.
Doug, Deacon, Spence, and Danny all secretly rent an apartment, but soon Deacon, Spence, and Danny move out and Doug lives by himself; Carrie tries to sell a condo to Kirstie Alley, which takes more work than she expected.
On the party for their eleventh anniversary, Doug and Carrie get a portrait of the two of them from Deacon and Kelly. They dislike it so much they stage a fake robbery to get rid of it.
It's Doug's 40th birthday and Carrie begins to try to make Doug realize that he should start wanting to do more with his life. So Doug decides he wants to ride a roller coaster that he was to afraid to ride when he was younger.
Carrie is finally fed up with Arthur, so she decides to put him in a retirement home. Doug, of course, is excited but after a touching story told by Arthur, Doug tries to decide whether or not Arthur should go.
