When Doug and Carrie notice that their really good friends Deacon and Kelly are spending time with a new couple, Doug and Carrie do whatever they can do to find new friends.
Carrie discovers a romantic line Doug once said when they were dating comes from a film where the main character said it to a monkey. Meanwhile, Danny falls for Holly and thinks she feels the same way about him.
When Doug delivers a package to his old high school, Doug reminisces about the time when he went there and played football, which makes him act very childish.
Deacon finds a new friend and Spence convinces Doug that the reason his has been spending time with him is that he is black; Carrie's mani/pedicurist 'cancels' her.
Carrie gets Doug to take Arthur on a recently won game tickets and trip to St. Louis after they make a deal that he never has to do anything with him any more.
Carrie gets Holly to go with her to Lowe's secretly because of her large van. A masculine waitress at a restaurant frightens Doug. Arthur and George pull a casino party to earn some extra cash which ends up backfiring.
During a snow storm: Carrie gets an iPod for free after a cashier is busy talking on the phone and accidentally does not scan it, but Carrie's guilty conscience gets the best of her.
When Doug finds out that he can earn a free Plasma screen TV at a timeshare ski resort, he tricks Carrie into going. But they both find out it will be difficult in getting that TV when the sales people enter the picture.
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 mothers 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.