Kevin and his family attend the wedding of his dad's boss's daughter. At the reception, Kevin tries to impress a girl by drinking champagne, Wayne recognizes that the bride was a former date and Jack's boss angers him by flirting with Norma.
Kevin is in need of extra cash when his allowance doesn't seem to go far enough. When Miss Farmer puts up an ad for someone to paint her house, Kevin jumps at the chance, thinking the job will be easy. But the task is bigger (and more expensive) than he could have imagined.
When Kevin's parents go away on a trip, he decides to invite Winnie over for a "night of studying". After he and Winnie inadvertently fall asleep on the couch, Kevin tries to impress the guys in the locker room by implying to them that they slept together.
When Kevin starts having car trouble, he asks Alice Pedermier to try and get him a good deal on a new car at her dad's dealership. However, when she dumps his friend, Chuck, Kevin has second thoughts about accepting anything from her.
After showing talent in gym class, Kevin decides to try out for the wrestling team. With a hard-driving coach and tougher competition, Kevin quickly realizes that it's a lot more than he bargained for.
Kevin and his classmates take a bus trip to the planetarium to witness the solar eclipse. On the trip, Kevin and Winnie have a fight after he calls her "too perfect" while Chuck gets locked in a restroom, leaving him behind.
When Kevin and his friends get together for their weekly night of poker, each of them is forced to face up to their problems. Chuck is worried about possibly becoming a father; Randy is failing Math; Jeff is accused of being a cheater; Paul and Kevin realize how much they've grown apart.
Kevin is having a hard time dealing with Winnie doing better than him on the SAT's. Jack is finding it hard to fathom Norma joining the workforce. What are the Arnold men to do? Take the girls out for a night of bowling, of course.
The Arnolds travel back to where Jack and Norma grew up to celebrate their high school reunion. But while Norma's parents are thrilled to see Norma, Kevin and Wayne, their enthusiasm for Jack isn't so pronounced.