Feeling at the end of their "privacy" rope, Roseanne and Dan decide to throw Becky and Mark out of the house. Becky confides that she and Mark are trying to get pregnant, so the plan to ask them to leave gets thrown out the window. Jackie argues with Fred about how she wants the baby to sleep in bed with them, and he wants Andy to sleep in his own crib. Upset, Jackie takes the baby and heads for Roseanne's already over-crowded house to stay there herself. To top it all off, D.J. is having a friend of his own spend the weekend. The straw that breaks the camel's back ...
Roseanne discovers that Darlene is seeing someone besides David, and that he knows about it, so she encourages David to fight for his relationship. Dan confides in Jackie that he is unsure how he feels about Roseanne's pregnancy, and finds comfort, but when he tells Roseanne about his insecurities, it blows up in his face. Roseanne confides in Jackie that she is having the same doubts.
Upset about Darlene breaking up with him, David tells the Conner's that Darlene experimented with drugs while away at school. Roseanne forbids Darlene to return to school, David volunteers to help "keep an eye" on her. Concerned that perhaps they are doing the wrong thing, and after confronting Darlene, Dan convinces Roseanne to at least reconsider her decision.
Roseanne and Jackie go to Chicago for Parent's Day, to surprise Darlene, and in hopes of meeting her new boyfriend, Jimmy. David wants to learn how to be tough, in order to compete with Darlene's boyfriend, who is a boxer, for her affections. Roseanne assigns Dan to help David feel good about just being himself. D.J. is getting picked on at school by a bully, but refuses to learn to fight back for fear that getting hit will hurt. Fred is impressed with Dan's parenting, until he figures out that Dan is only doing what Roseanne tells him to.
Dan and Roseanne find out that D.J. wants to skip participating in his school play because he has to kiss a black girl, and is uncomfortable about it. Roseanne wants to force him, and Dan is worried that D.J. might have gotten prejudiced ideas by something he has unwittingly said or done. Jackie is perplexed by the fact that Fred seems to enjoy spending time with her mother.
It's a Thanksgiving full of tension and anxiety when Roseanne gets alarming news about her baby from the prenatal clinic. The discomfort is only worsened when Nana Mary shows up with her new husband and upsets Bev, and the rest of the family, by discussing the two abortions she (Nana Mary) had years before.
Tensions are heightened at the Connor house as a short-fused Roseanne waits for the amniocentesis results. Dan tries his best to help devise a solution and comfort Roseanne but his good intentions are misinterpreted. Everyone seems to have an opinion on the situation, which only angers Roseanne and intensifies her doubts and fears.
Roseanne and Dan are called down to the school to see D.J.'s teacher because he refuses to write his homework on the board, and his teacher is concerned that D.J. may have a learning disability. Dan discovers that it is not because he can't do the work, but because he is at that age where boys sometimes get an involuntary erection, and D.J. is embarrassed to stand up. The family meets David's new girlfriend, Dinah. Darlene discovers that David is actually developing feelings for Becky.
After being arrested for D.U.I., Beverly is forced to attend Alcoholics Anonymous (A.A.) meetings, where she discovers that she might really be an alcoholic. This new realization does not bode well for the family, since Roseanne is forbidding anyone to drink while Beverly is in the house, which quickly puts an end to Dan's super-bowl party. Dan, Jackie, and Fred sneak out to the garage to drink and watch the game on an old portable TV, until Beverly catches them, and pitches a fit, prompting Roseanne to pitch a fit, or two, of her own.
Roseanne pretends to be ill in order to get some rest and relaxation to the exhaustion of everyone else in the family, who are at her beck and call. David discovers Roseanne's faking but when he confronts her, Roseanne strikes a deal with him that he reluctantly accepts. Meanwhile, Jackie confronts Beverly about being an awful mother and is stunned by her reaction.
Fred tells Jackie that he doesn't want D.J. to visit their house so much anymore, because he gets weirder every time he comes over. In order to protect Fred, Jackie tells Roseanne that she is the one who has a problem with D.J. constantly being at her house, which infuriates Roseanne. Dan tricks Darlene into coming home for the weekend and tries to make the girls stop bickering for their Mother's sake. D.J. expresses a strange, new fascination with eating cardboard.
The green-eyed monster emerges in force between David and Mark when they both become interested in Stacy, a waitress at the Lunch Box, whom David asks to pose for a wall mural. Jackie thinks her sex life with Fred needs spicing up while Fred is happy leaving well enough alone.
Fred is still angry and bitter about his separation from Jackie while Jackie is beginning to see the sliver lining and starts going on outings that Fred never enjoyed. Meanwhile, Roseanne begins meddling in order to get the two of them back together but begins to regret it when she realizes how unsure Jackie is that she even loves Fred anymore.
Mark and Becky find a tiny run-down trailer in a trailer park, and decide to make it home. Determined to fix up their home all on their own, they turn down offers of assistance from Dan and Roseanne, who in turn have to find covert way to help the kids out. Roseanne discovers that they will need to come up with $2,000 to prepay for the baby's doctor and hospital stay.
Dan lays down the law when DJ lets a pushy, aggressive girl order him around but Roseanne likes the girl in question. But when the relationship lands DJ in trouble at school, Roseanne has to intervene. Jackie and Fred go to marriage counselor to help solve their relationship problems.
The Conners are selected to be a "Neilsen Family". Roseanne, who is going through a nesting period in her pregnancy, insists that the family watch nothing but educational-type programing to prove to the Neilsen people that they are not white trash. After Dan breaks the couch, Roseanne accepts a hand-me-down couch from her Mother, but soon regrets it. Jackie and Fred make a life-altering decision.
David announces to the Conners that he wants to spend a month in Europe after graduation, but Darlene selfishly pressures him out of it. Dan starts working on building his boat again, but Roseanne insists that they can't afford it, and makes fun of his dream, launching into a fantasy where she and her family play the castaways on Gilligan's Island. Cast members from Gilligan's Island cameo as members of the Conner family.