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.

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.

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.

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.