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.

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.