D.J.'s old bedroom is being converted into a nursery for the new baby. After discovering that a new baby crib is out of her price range, Roseanne schemes up a baby shower in hopes of getting at least forty $10.00 gifts, that she can exchange for the $400.00 crib. This plan threatens to backfire when the gifts are mostly homemade, or are otherwise nonexchangeable. After being unable to work together to paint the nursery without squabbling, Roseanne reassigns Becky and Darlene to throw the baby shower instead, but the girls are still at each other's throats because Darlene refuses to pull her weight, sticking Becky with all the work. Roseanne gets David to throw a "guy" baby shower for Dan with the men at his shop, hoping for even more exchangeable gifts, but that backfires as well.

Roseanne sparks a fight with Jackie when she feeds Andy junk food against Jackie's orders. Dan spends some "quality" time with DJ to show his son that he does more than watch television and drink beer all day.

A new diner is opening up across the street from Roseanne and Jackie's diner, and they are worried that it will spell the end for "The Lunch Box". To promote the new restaurant's grand opening, the owners hire Pat Harrington Jr., who played Dwayne Schneider from the 70's sitcom One Day at a Time (1975). When Roseanne discovers that they have a salad bar, and are serving loose meat sandwiches, she declares war. When adding a waffle bar, staying open late, and dressing up the menu doesn't seem to work, Roseanne decides to sabotage the new diner with raw fish, only to wind up stuck in an exhaust vent over a stove. The cast of Stomp does a dance at the diner.

Roseanne and Dan decide to go out on the town one final time before the baby is born. After finding out that their diner table at the nice hotel they're staying at will be unavailable for quite some time, they crash a Bar Mitzvah taking place in the private dining room. Becky and Darlene discover a bottle of peppermint schnapps at the restaurant after closing and get wasted.

Roseanne goes into labor on her favorite holiday (Halloween) and gives birth on a pain-medication-induced psychedelic trip.

The Conners are caught in a time warp back to the 1950s in which Roseanne is a cheerful, frilly housewife, Dan is the head of the house, Jackie is an eccentric next door neighbor, Becky is a poodle-skirt wearing teenage girl with a hunky boyfriend, David is an exchange student from Canada, and DJ is an aspiring rock star who's under pressure from his dad to be a football player.

Roseanne and Jackie's shopping trip turns into a road trip when they pick up a hitchhiking teenage girl. Dan gives Mark relationship advice that severely backfires.

DJ's teacher lets the class design their own Thanksgiving pageant, which turns into a Pulp Fiction spoof that offends many parents. Roseanne invites some new Native American friends over for Thanksgiving.

Dan is regretful and depressed when his old band comes to town to play a gig. Roseanne talks the band mates into giving Dan a chance onstage, which he enjoys to the fullest.

Roseanne narrates a video for her baby and wants everyone in the family to have a part in it. Darlene and Becky find Dan and Roseanne's old love letters. Fred is determined to seem intelligent and interesting to Jackie but only succeeds in making her feel more crushed by their divorce. Dan attempts to comfort Jackie while Mark prepares a special dinner for the family.

Roseanne finally gets to meet Leon's fiancé, Scott, and learns that they are planning a wedding. In order to free Leon up to travel to Minnesota to meet the minister, Roseanne volunteers to finish planning the wedding - which becomes "one gigantic, offensive, Roseanniacle ball of wrong". Leon develops a bad case of cold feet, and it is Roseanne to the rescue.

Roseanne and Jackie get jobs as product promoters in the local supermarket. Once they start giving out samples, however, sibling rivalry takes over. Roseanne's jealousy runs high when Jackie begins outselling her and their friendly competition turns into a literal food fight.

The Conners receive a small inheritance from their Great-Aunt Harriet and decide to spend it on a nice dinner out. The evening takes a dark turn when Darlene unexpectedly comes home. She spends most of her time alienating and insulting her family until a surprising fact about her is revealed and her family bites back.

Mark tries to cheer up a glum Becky by inviting the family over for a surprise get-together. As the night goes on, Becky's mood only worsens which prompts Roseanne to pull her aside for a heart-to-heart talk. Becky admits she feels like she missed her chance to go to college and become a therapist or an EMT. Becky even admits to having second thoughts about her marriage to Mark.

Nana Mary visits Roseanne and Jackie at Jackie's house, and brings a box of their childhood belongings. Among them was a doll that Jackie thought was lost forever, and causes a huge fight when Jackie realizes that Roseanne was the one who hid it from her all those years ago out of jealousy. Dan has a poker game at the house, and Roseanne convinces him to invite Leon and Scott, but is worried that they will spend the whole night nagging each other like housewives. The men have a spirited discussion about how blacks, gays, and poor white men are looked upon in this country.

Dan is at a crossroads when a promising new construction job opens up that could make him and his old crew a lot of money. He struggles with whether to continue his job at the garage or to strike while the iron is hot on the construction job. Meanwhile, Jackie reluctantly starts using the internet on her new computer and is amazed how much she likes it. She becomes so obsessed a concerned David has to intervene.

The Conner family decides to throw caution to the wind by spending Dan's last paycheck from the garage on a vacation to Disney World.

Magic, wonder, and whimsy surround the Conner family on their tour of Disney World. The only person not amused is Darlene...until she meets Winnie the Pooh.

David moves out when he gets a job at a strange local theme park. Soon, David is transformed into "Hans the Hare", a hyperactive and perky park employee. Roseanne steps into action in order to get the real David back.

After proposing marriage to David, Darlene tells him that she is pregnant. They plan to wait to tell the family, but Roseanne smells the fear and jokingly guesses, correctly, that Darlene is pregnant. Dan is convinced that they are not ready to start a family, and is openly not happy for them at all. Roseanne, knowing that there is nothing she can do, feigns happiness and tries to give Darlene advice and support.

A producer and reporter from "Wake up Chicago" come into the diner wanting to do a "Man-on-the-Street" interview about the diner owners - to which Roseanne, Jackie, and Leon readily, and eagerly agree. Leon stumbles through his interview nervously, like a deer caught in headlights. Jackie babbles through hers like a hyper manic who's been off her medication. But Roseanne nails her interview, and gets a job offer to do a one-minute spot on the air - where Roseanne gets to speak her mind about whatever she wants. God help TV.

Bev is smitten with her charismatic ballroom-dance instructor until he starts putting the moves on a newly divorced Jackie. When Jackie agrees to a date with the instructor, jealousy takes hold of Bev.

Darlene and David get married. Dan suffers a heart attack during the ceremony.

Dan is rushed to the hospital after having a heart attack and Roseanne tries to pull herself together while she's stuck in the waiting room.

Dan returns home from the hospital but Roseanne finds out he's not sticking to the doctor's orders.