Dan, Fred and Mark enter the realm of 'too much information' when their wives confide in one another, then spread the word back to the men about their sexual activities (or lack thereof).

Dan and Roseanne find out that D.J. wants to skip participating in his school play because he must 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 that Fred seems to enjoy spending time with her mother.

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.

In Roseanne's absence, Dan discovers something troubling about Jackie and gets some sound advice from David.

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.

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.

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.

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.

After finding out they won the Illinois State Lottery, the Conners and family imagine how to spend their new-found wealth. Kathleen Sullivan and Robin Leach interview Dan and Roseanne in their home. Throwing a party in their home proves that people really do come out of the woodwork to help celebrate wealth. Dan and Roseanne vow to not let money change who they are.