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.

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.

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.

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.

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.

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.