When Dan receives a $500 advance on a drywall job, everyone hopes there will be money left over for something extra for themselves. When it turns out that, after the bills are paid, there will barely be enough left to buy one thing, Dan and Roseanne each buy themselves a luxury item on the sly. Darlene is scolded for lying, but they each ask her to hide the truth about something.
Roseanne and Dan plan a romantic dinner date out, and run into an old friend that they were unaware had been divorced. When they learn that her divorce was because her husband refused to allow her to follow a dream, that Roseanne inspired, Dan wonders if Roseanne will grow to feel the same way. When Jackie is late for baby-sitting, Becky is allowed to cover, much to the delight of the kids.
While making his famous chili, Dan awaits a phone call about a badly-needed construction job, and has to run Jackie off the phone. Dan expresses his annoyance with Jackie always being over at their house to Roseanne, but while Dan and Roseanne are taking a relationship test in the back of a teen magazine for fun, his annoyances about Jackie come to the surface in front of her. When she comments that he wouldn't even notice so much if he had a job, Dan is pushed too far. Darlene is making a castle for extra credit because she is flunking History, but D.J. accidentally ...
Roseanne wants Dan to enter a country music song-writing contest sponsored by the local radio station. Dan is reluctant to do so until he finds out that the grand prize is a hundred dollars. Unable to come up with a new idea, and not pleased with anything he wrote in the past, Dan chooses one of Roseanne's old poems to put to music. Sexual tension between Jackie and Booker heat up in the workplace. Becky and Darlene are at each other's throats.
Roseanne talks Booker and the women from work into going bowling. Becky gets dolled up for the night out, because she has a first crush on a boy from her school that works at the bowling alley, but is mortified at the thought of being embarrassed by her parents. Jackie and Booker make a "friendly" wager involving a sleepover vs. toilet bowl scrubbing.
Dan hires a photographer to take a family portrait at the house for an upcoming high school reunion. Everyone is dressed up and posed when Jackie lets the cat out of the bag about a fling Dan had back in high school with Roseanne's nemesis.
Upset because she got dumped again, and certain she will never find a good man, Crystal turns to Roseanne and Jackie for support and advice. Booker turns down a date with Jackie because his "Mother" is in town, and turns up at the Lobo Lounge with another woman. Jackie decides not to turn the other cheek. Praying for a snow day, Darlene procrastinates doing a book report she has to turn in the next day.