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, he begins to reminisce (and exaggerate) about his old high school daze and 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 persuades Holly to go with her to Lowe's because the van has more cargo room. A macho waitress at Slappy's Diner threatens to kick Doug's ass after he insults her. Arthur and George throw a casino party that 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.