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 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.

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.

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.

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.