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.

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.

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.

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.

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.

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.

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.

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 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.

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 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.

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.

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.

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.

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.

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 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.

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, 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.

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.

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.

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.

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.

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."

While Kevin tries to take his relationship with Winnie another step, Wayne's friend Wart returns from Vietnam a changed man. Kevin decides to steal the opposing team's mascot at the homecoming football game, but the childish prank is overshadowed by a realization of how Wart has been affected by the war.

It looks like the father-son fishing trips might come to an end when the lastest outing is plagued with problems.

When the Arnolds attend the wedding of Jack's boss' daughter, one of the bridesmaids turns her attention to Kevin. He tries to get a bottle of champagne for them to consume together, but ends up drinking it while he waits for her. When she does arrive, Kevin vomits on her. Later, Wayne tells Kevin that he's had sex with the bride.

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.

Kevin gets jealous of a charismatic political campaigner who has encouraged Winnie to help him out.

Some people never find true love, but Kevin believes he did. He had what most people search all their lives for, but he blew it. When Winnie comes over for a study session while his parents were away, Kevin wants to relationship to go further. Winnie sees through his plan. She does stay, but they just fall asleep together. The next day, though, he tells his friends a different story. When Winnie finds out, she dumps him.

Wayne has fallen head-over-heels for Bonnie, a 23-year-old divorcee who has a child. Norma and Wayne fight about him wanting to move in with her. Kevin, meanwhile, is feeling lonely and wants desperately to talk with Winnie - to apologize and because he realizes he really needs her.

It's another day of work for Kevin, who keeps calling Winnie when he can - even though he keeps getting in trouble with Mr. Chong because of it. Kevin also feels he is in competition with the pizza delivery guy.

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.

Wayne seems to be a changed man, considering his relationship with Bonnie and her baby. Kevin longs for a romantic vacation with Winnie, but must face reality on New Years Eve when Bonnie leaves Wayne for her ex-husband.

When Kevin is offered a great deal on a used car from Alice's dad, Pistol Pete, Kevin has to decide whether to betray his friend, Chuck, who has broken up with Alice again.

Kevin wants a story that he and Winnie can tell their kids. So, when he is grounded after receiving a speeding ticket, he sneaks out of the house anyway. Kevin, Winnie and friends are off to see The Rolling Stones, who are rumored to be playing at Joe's place, which is out of town. But when they arrive, Joe says he doesn't know who the Rolling Stones are.

Kevin's new friend, Jeff, was the first kid he ever knew whose parents were divorced. Winnie has Kevin set Jeff up with Ann, but Jeff is feeling guilty about the girlfriend he moved away from. Ann is upset that Jeff doesn't want anything to do with her and Winnie blames Kevin! To sort everything out, Kevin drives Jeff to talk it all over with Julie.

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.

When Kevin and friends are asked to write down the ways they feel inferior, they have trouble thinking of something. They don't have any problems picking on the new girl with the big nose. Ricky decides to ask her to an upcoming dance anyway, but all his friends laugh at him - none of them realising how insensitive they are being.

On the way to the Planetarium, Kevin and Winnie and Alice and Chuck play "Truth or Dare." When Winnie asks Kevin what he'd change about her, he thinks and then says sometimes she is just too perfect. She doesn't appreciate this and tries to prove that she make trouble as well as anyone else.

Over a game of poker we learn some truths about Kevin's friends, including that Chuck thinks he's gotten Alice pregnant, that Randy is worried about failing trigonometry and that Paul and Kevin are drifting apart.

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.

The Arnolds fly across country so Norma can attend her 25-year class reunion. Her parents keep talking about her old boyfriend, Roger, which upsets Kevin, but not Jack. Kevin realizes that the bond between his parents is stronger than he realized.

It is summer and Kevin is working for his dad in the furniture factory. He is getting frustrated and wants to take off with Jeff and Chuck on a road-trip, but he can't. Winnie, what's more, is working away from town and Kevin wants to visit her - so he quits his job and leaves town. When he gets there though, he finds that he is not wanted and that Winnie has fallen for a lifeguard named Eric.

After Kevin loses all his money and his car in a poker game, he decides he has to leave the resort - there's nothing to keep him there now. The next day he says goodbye to Winnie, punches Eric and storms out. Hitchhiking out of town, he runs into Winnie who has been fired from her job. They begin to argue and lose the ride they had flagged down. Later, sheltering in a barn they talk about how much has changed between them. Winnie thinks it's just inevitable - that everyone grows up. Kevin doesn't want to believe it and neither does Winnie, not really. They kiss, passionately. The next day they both return to Kevin's hometown for the last 4th of July he will ever spend there. Karen has returned home and she is pregnant...