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."
Summertime used to be fun, but now everyone's gotta work. Kevin has a job at a Chinese Restaurant with Paul, but one day - after finding a Christmas card he received from Cara, decides he will visit her at the lake. Paul has no choice but to tag along because Kevin is driving. Kevin feels like recapturing the wonderful time he had last summer, but things don't go to plan.
While Karen has agreed to marry Michael, she has not agreed to have a traditional ceremony like her mother wants. She also doesn't know how to tell her family that she and Michael are moving to Alaska, where he has found work.
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.
When Kevin's parents go away for the weekend, he invites his friends around for a poker game. But when the game gets boring, Chuck and Ricky call all their friends and Kevin ends up throwing the mother of all parties at home - ruining the house. Norma and Jack return the next day, earlier than expected.
Kevin, Ricky and Chuck plan on sneaking into an R-rated movie, while Paul decides he'd rather stay home and talk marine biology with a family friend's daughter. Kevin, Ricky and Chuck get thrown out of the movie theatre where "Carnal Knowledge" is playing, while Paul is at home losing his virginity. Paul confides in Kevin, but his secret gets out the next day.
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.
Kevin is on a first-name basis with McKinley's High's basketball hero, Bobby Riddle. When the team makes it to the regional finals, Kevin's dad decides to attend the game and embarrasses Kevin by talking strategy with Paul and Chuck. Later, though, Kevin apologizes to his dad for how he treated him.
Kevin wants to date Inga and he uses Winnie to help him get a date. Winnie does the same thing to Kevin, getting set up with new guy Matt Stevens. They end up double-dating at the Spring Dance, bringing some tension to the evening. But when Matt and Inga begin to dance together, Winnie and Kevin rediscover their feelings for each other.
Kevin has been dating Julie Aidem for two weeks when she invites him for dinner with her family and asks him to tell her parents they are going steady. When he sees Mr. Aidem is dominated by Mrs. Aidem, Kevin decides he doesn't want to end up like that and breaks up with Julie.
While Kevin is asked to consider his future, Wayne makes a decision to leave school and join the army. Jack and Norma try to talk Wayne out of it, but he won't listen. Wayne and his friend Wart go together to the army testing station. Jack follows and apologises to Wayne for not being a better father to him.
Miss Shaw was one of Kevin's more memorable teacher's. She was young, black, anti-authoritarian and actually enjoys teaching. But her unorthodox methods get her in trouble with the school board.
Grandpa Arnold is getting old and is involved in a minor car accident. He isn't ready to give up his driver's licence until his grandson, Kevin, tells him what he needs to hear.
Kevin is motivated to get his driver's license by the promise of a date with Jessica. But Kev can't parallel park and he whimps out of taking his test and lies to his family about getting his temporary license. When Kevin tries to practice at night, he runs over the lawnmower - leading Jack to discover the truth about Kevin's license.
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
Kevin doesn't want to attend his family's annual Christmas party for the neighborhood because it will only be his parent's friends - all his friends will be away. Jack is busy at work and Norma is busy at college and when several other problems crop up during the party, Norma and Jack argue. When Jack sends Kevin and Wayne to the store, they expect to return home to the worst.
It's dinner out for Jack's forty-third birthday. But Jack is grumpy, mainly because he is still not talking to his daughter. Norma and Michael try to mediate the arguments between the two, but the dinner - which Kevin is paying for - ends badly.
Kevin joins the school's soccer team in an attempt to become involved in school sports, but becomes very frustrated with the team's lackluster performance and an extremely apathetic coach.
Kevin does not understand why Wayne's new girlfriend, Sandy, is with him. The tables are turned when Sandy approaches Kevin behind Wayne's back and kisses him. In fact, they kiss all over the school. But when Sandy breaks up with Wayne to be with Kevin, Kev can't bring himself to betray his brother.
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.
Denise and Frank seem to be made for each other, until Denise turns her eye to Kevin because he understands poetry. Although she breaks up with Frank and kisses Kevin, Kev thinks it would be better if she went back to Frank because they are a perfect match.
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.
Kevin's first day of high school is not all it's cracked up to be. He tries to set himself up as the class clown, but it backfires. He is hassled by a nerd and his new teacher, Mr. Botner. Even Winnie can't make him feel better.
The Arnold and Pfeiffer family go on a joint family trip. Kevin meets a wild young girl who smokes! Kevin and Cara have a good time together, so much so that he ditches dinner with his family to see her one last time - expecting to never see her again.
