Kevin and his father endure a disastrous trip together to buy a suit for Kevin. They get lost and argue over the radio station and Kevin embarrasses Jack at a diner they stop at.

Jack wants to help Karen out by fixing up the house she is now living in. But father and daughter go head-to-head when he discovers she is living there with a man.

Fed up with the low pay at his first regular job, Kevin decides to try for a job at the mall where he can meet girls. He demands a pay rise, not expecting to get it. When he does, he quits anyway.

When Ricky Halsenbach turns 16, Kev and friends decide to go cruising for chicks. Kevin gets into trouble with Cindy after she catches him in a lie. Purdle moons Kevin's parents from Ricky's car.

The Pfeiffer and Arnold families have always been friends, but that friendship is threatened when the Pfeiffers come into a lot of money due to a real estate investment that Jack Arnold passed on. When the Arnolds are invited to the Pfeiffers' country club, Jack cannot handle it. Norma saves the day with a toast to the families' continuing friendship

It's lunchtime at McKinley High and the cafeteria is full of life. Chuck spies a potential date. Ricky worries about an assignment he is yet to finish. Wayne tries to win $20 by finding out Maniac's first name. And Kevin is convinced by Winnie to donate blood.

When Karen returns home one night, Kevin and Wayne's living arrangements are thrown into chaos. She's had a fight with Michael and they're not talking. Jack discovers that Michael had asked Karen to marry him, but she didn't want to do anything so traditional. Michael camps out on the Arnold family front lawn in the hopes of getting Karen back. Ten days later, Karen proposes to Michael herself.

Kevin is torn between whether to try getting back with Winnie or just enjoying his time at the diner with friends. Includes flashbacks of Winnie in the pilot, "Steady as She Goes," "Nemesis," "How I'm Spending My Summer Vacation," among many others. There is also a flashback to Becky Slater in "Just Between You and Me and Kirk and Paul and Carla and Becky," to Lisa Berlini in "Dance with Me" and to Madeline in "It's a Mad, Mad, Madeline World."

Kevin wants to earn some money to take Winnie out for dinner, so he jumps at the opportunity to paint his sociology teacher's house. When he tries to con some younger students into helping him out, things start to go wrong.

While Kevin and Winnie are concerned about their futures, Jack gets a disappointing evaluation from his employers at NORCOM. Kevin doesn't want to end up in a job like his dad has and Jack is getting pretty tired of it, too.

It's Christmas and the Arnolds have a lot to celebrate. Things begin to unravel though, when Kevin thinks Winnie has bought him an expensive present and he wants to do the same in return. And Jack's new business gets into trouble when his partner, Charlie, decides to drop out and return to NORCOM.

Kevin discovers that he's pretty good at wrestling. He thinks about giving up until he realizes that Winnie likes him being an athlete. The coach even talks Kevin into going into competition.

Kevin and his dad don't know what to do about the women in their lives. First, Winnie has out-scored Kevin in the SATs and is thinking of applying to Harvard and Princeton. Second, Norma has gotten a job as a financial supervisor, leaving Jack to think she'll neglect her household duties. When the two Arnold men realize that the women in their lives are upset at their attitudes, Kevin takes Winnie to the bowling alley to apologise, only to find his dad has done the same thing for Norma.