Part 1 of 2: D.J. is busted at school for having obscene reading material. Dan meets with the principal, but dreads it, because he is certain that the reading material D.J. brought to school is one of his porno magazines. He soon discovers that the reading material is far more sick and twisted than just a skin magazine; begging the question of where D.J. got it, and leaving him speechless by the answer. Roseanne and Dan discover that Jackie has been keeping a dark secret, and each of them try to help her by dealing with it in their own, unique, way.
Part 2 of 2: Dan gets bailed out of jail by an amused Darlene, while rumors fly from wild to wilder, as to why he was arrested. Jackie learns why Dan was arrested, and finds herself both angry with, and touched by Dan's protective gesture. Overwhelmed, and feeling like things are moving too fast, Jackie leans on Roseanne to help her move out of Fisher's apartment. Roseanne lovingly declares that her family is officially "Poor White Trash".
The Conners prepare for the 'Founding Fathers Day' celebration in Lanford. Roseanne sets up a food booth, where she meets the one and only, Loretta Lynn. D.J. and his Woodchuck Troup, put on the town play reenacting the signing of Lanford's incorporation. Their family's own founding father, Dan, gets a job selling hot tubs. And last, but not least, Darlene protests the Conner's involvement in the whole "meat industrial complex" with vandalism at her mother's diner that lands her in more than just hot water.
Roseanne and Dan plan a romantic dinner date to celebrate their twentieth wedding anniversary, but struggle with what to give one another. Dan finds out that Roseanne has decided on something expensive for him, so in order to get Roseanne a nice gift too, he takes a temporary job at Maury's Big and Tall store. His gift idea (and the job to pay for it), which seemed like a good idea at the time, soon blows up in his face.
Tired of having their Mom hanging around them all the time, Roseanne and Jackie try to encourage a relationship between Beverly and Jake, her friend from the retirement community they both live in. Molly comes on to, and kisses David, making him nervous and uncomfortable. To back her off, David confesses the plans he and Darlene have for the future, like possibly dropping out of school and running away together. Having seen and overheard this strange exchange, D.J. confronts Darlene with what he knows, and asks her if any of it is true, prompting Darlene ponders ...
After some prodding from (and striking deals with) her Mom, Darlene agrees to go to the prom with David, where she has a surprise deal of her own for her boyfriend. Roger attempts to strike a deal with Dan, using the temptation of being able to make him a ton of money, but is met with a mixed reaction from the Conners. Roseanne attempts a surprise fix-up between Jackie and Roger for a couples' night out, but to Roseanne's surprise, Roger shows up with a date. His choice of date is a jaw-dropping, shock to everyone.
When it looks like the fixer-upper house Dan has invested in is going to pay off, the Conners are on top of the world. But when the buyer backs out, and one partner skips out, and the bills are due on the project-house, that world threatens to come crashing down. Pushed by Beverly's latest attempt at driving Jackie insane, Jackie finally blurts out to her Mom that she has been seeing a psychiatrist. Nancy decides she wants to have a baby, but her chosen sperm-donor turns out to be a real rotten egg. An unlikely source rides in who just may save the day for the Conners.
D.J. comes running in the house with a skinned knee. Dan and Roseanne take him to the kitchen to get fixed up, but when Dan slings open the freezer door to get ice, he accidentally hits Roseanne in the face, knocking out a tooth. After a few failed attempts earlier in their relationship, Darlene and David finally have sex for the first time. They also get the responses to their college applications. David doesn't get in, but Darlene does, prompting her to hide the truth... at first. Determined to be allowed to go to this art school in Chicago, Darlene enlists her Aunt...