Kevin is heartbroken when he finds out Winnie is dating one of the other lifeguards. Forced to return home by hitch-hiking, Kevin and Winnie must wait out a storm together in a barn.
Kevin chases after Winnie who has taken a job at a out of town country club as a lifeguard.
The Arnold's go back to Norma's hometown to attend her 25-year high school reunion.
It's a case of the men vs. the women when Winnie scores higher than Kevin on her SAT's; and Norma gets a high-paying job in a new company.
As Kevin and his friends play poker, we learn that Chuckie fearing his girlfriend may be pregnant, Randy is failing at school, and Paul is too stuffy for the other guys liking.
A school field trip finds Winnie upset at Kevin after he says that she is perfect during a game of truth or dare.
Kevin's friend, Ricky, falls in love with a girl that has a huge nose. Ricky's feelings are hurt when he overhears the guys joking about it.
Kevin feels he has been recruited to be on the school's wrestling team, but when the coach pushes him to try harder, he thinks about quitting.
Kevin and Winnie fix Jeff up with the new girl in school. However, Jeff is reluctant to commit to the relationship because of his attachment to an old girlfriend back home.
Kevin, Winnie and the guys follow a rumor that the Rolling Stones are playing in a bar just out of town, but to get there Kevin must sneak out in his dad's new car.
Kevin can get a great deal on a car from Alice's father, but fears she is falling for him.
New Year's finds Wayne and Bonnie treating the Arnold family to dinner at a nightclub, but ends-up in heartbreak when Bonnie reunites with the father of her son.
After seeing Winnie at the mall with a big Christmas gift in hand, Kevin feels the need to buy her something special. Meanwhile, Jack is trying to get a loan to buy a new business.
Jack is frustrated after getting a lukewarm evaluation as "competent" at work. Meanwhile, Kevin, Winnie and Paul are all studying for their SAT exams.
Kevin's new job as a Chinese food delivery boy has him too busy to spend time with Winnie.
Wayne has a new girlfriend Bonnie, a 23 year old divorcee with a baby.