Carrie is excited to attend her company's retreat but Doug is dreading it and in a fit of boredom he lies to Carrie's boss and tells him he has climbed Everest.
After Arthur smashes Doug's pumpkin and forbids Halloween, an angry Doug decides to go overboard with decorations, causing Arthur to have a heart attack.
Carrie and Doug argue over getting life insurance in order to care for her father and install an Arthur cam to watch him while he is alone in the basement.
When Barb announces that she and Pete are divorcing, Christine agrees to let her move in and tries to be supportive; Matthew is forced to move in with Richie.
After admitting her attraction to Stan, Christine feels guilt from Marly and Lindsay into serving lunch at Ritchie's school and finds herself serving with Stan.
Ritchie gets to go on a playdate with his fourth grade teacher Mr. Harris after Christine wins a raffle; Richard's father-son plans could spoil the fun.
The Conners take a trip back to the 1950s, living the life of the sitcoms wherein Roseanne is the always happy housewife and Dan is the workhorse husband.
D.J.'s teacher decides to give his students free reign for the upcoming Thanksgiving pageant which begins to upset some of their parents about the idea.
Dan's old band visits Lanford to play, but when Dan thinks the band will let him back in to play this show, he is denied and becomes upset over the issue.
While Roseanne creates a video time capsule, Becky and Darlene find some old love letters and D.J. is upset to learn that his baby book was never done.
Roseanne and Jackie decide to take up jobs at the local supermarket demonstrating new products, but their sibling rivalry gets the better of them both.
The Conner family receives some inheritance from their recently passed Aunt Harriet, so they decide to go out for a nice dinner until Darlene shows up.
Becky is still feeling depressed as Mark plans a surprise get-together with their friends and family, but it still has no effect on her and her aspirations.
Dan is given an offer by his old crew that leaves him confused on what to do since his current job is steady, but he could make a lot of money with this offer.
The family becomes elated when Dan brings home his final check from the Lanford City Garage and announces they are going to Disney World for their vacation.
The Conners arrive at Disney World for their vacation that everyone is excited about except for Darlene, who just wants to sit there until it is time to go.
Darlene shocks both the family and David when she proposes to him, but he gets another surprise announcement when she informs him that she is pregnant.
Bev has quickly become attracted to her new ballroom dance instructor, but becomes infuriated with him when he begins flirting with the divorced Jackie.
Jerry gets a date with a Miss America contestant, only to be foiled by Kramer, who acts as a chaperone; Elaine gets a job as Mr. Pitt's personal secretary.
George gets upset when his girlfriend is thanked for a dinner he bought; Jerry becomes obsessed when he finds that his current girlfriend once dated Newman.
In an effort to please his new girlfriend, Jerry agrees to host a pledge drive for PBS; George is convinced that a waitress keeps giving him the finger.
Jerry feels misled when his mysterious Chinese date ends up not being Chinese; Elaine ruins her friend's latest relationship with a man who likes to talk.
Jerry's excitement about dating a gymnast diminishes after bad sex; George's girlfriend catches him eating out of the trash; Kramer passes a kidney stone.
Jerry accepts an Armani suit from Kenny Bania, provided that he will treat him to a meal; Elaine dates a bouncer from England; Kramer decides to eat fresh.
George passes up hiring a beautiful secretary for an ordinary woman, in the hopes of less distraction; Jerry catches his dry cleaner wearing his clothes.
Jerry attempts an impossible switch when he finds that he likes his girlfriend's roommate more than her; George is convinced that his new girlfriend is bulimic.
Carrie remembers her wedding day and how she was looking for a sign from God that Doug was right for her; Arthur makes Doug's family to pay for the wedding.
Carrie is hurt that Doug thinks of himself first when their plane makes an extremely rough landing and he takes the only available oxygen mask for himself.
Carrie worries that Doug will embarrass himself when her boss asks him to testify in a court case as the expert witness; Danny and Spence fight over Holly.
Christine receives a notice from Ritchie's private school that his tuition is going to rise and decides that some expenses are going to have to be cut.
Ritchie does a horrible job on an assignment for his snobbish school, which will be put on display, and Christine makes Richard responsible for the monstrosity.
Richard attempts to get Ritchie's interest in his career; Christine, being a helpful sister, tries to re-ignite the relationship between Matthew and his ex.
Richard's unbelievably attractive brother Joe stops by for a visit and has some surprising news, news that Christine discovers after she sleeps with him.