As Winnie Cooper deals with the passing of her brother Brian, Kevin and Paul contend with the ups and downs of sex education. Feeling that Coach Cutlip isn't teaching them what they need to know, Kevin and Paul try to get their hands on a copy of the book "Everything you wanted to know about sex, but were afraid to ask."
Kevin's older sister Karen doesn't communicate with her parents anymore, and it's all because of her new boyfriend, Louis. And things are only made worse when Louis comes to dinner. Kevin finds out that Louis is cheating on Karen, but suspects that Karen already knows and is fine with it. Only, she doesn't know, and when finds out, she's not fine with it.
Kevin asks Lisa Berlini to go to the dance with him. She agrees to go with Kevin, but when Brad Gaines asks her to go, Lisa decides to go with him instead of Kevin. While sitting with Winnie and Paul during lunch, Kevin feels himself falling back in love with Winnie. Kevin asks Winnie to go to the dance, but she's already going with Kirk McCray. Kevin tries to make Winnie jealous by asking a random girl to dance with him right in front of Winnie.
Kevin gets a crush on his English teach, Miss White, who convinces him to play Robert Kennedy in a play she has written about Martin Luther King. Only, he's having trouble getting her to see him as more than a 7th grader.