Dobie believes his life is in shambles, all the fault of Max Shulman, the creator of this show and of the character of Dobie himself in the book "The Many Loves of Dobie Gillis", and thus the person who has placed him in all his misadventures. Dobie thinks about quitting the show altogether because of all the problems he will be facing episode after episode. Many of the other people who will be appearing on the show try to talk Dobie into changing his mind.
Dobie launches a runway offensive versus wealthy, better-dressed hunk Milton Armitage, his competitor for luscious teen gold-digger Thalia Menninger. When Dobie's grocer father Herbert T. Gillis refuses to finance a clothing binge, Dobie talks a local haberdasher into letting Dobie secretly model the shoppe's best outfits, to promote the store's business, plus counter Maynard & The Beat Generation's anti-fashion values, which challenge 50's Mad Men mores.
When Dobie starts singing like Elvis Presley, he finds that it drives the girls at school wild. What's even better is that Thalia Meninger, the love of his life, has taken notice and decided to become his manager.
When Maynard returns from a short hitch in the service and falls for Dobie's girl Pearl, will Dobie do that far, far greater thing than he has ever done before and step aside for his love-struck friend?
With the big football game coming up and Central High doomed to lose, Dobie, Maynard and their friends plot to steal Webster High's mascot, a goat which Webster players traditionally pet for good luck just before games.
Dobie and Maynard conspire to get leading man Milton out of the way by opening night so his understudy Dobie can star opposite the lovely Annabelle in the school play, "Magnolias at Manassas: a Drama of the Civil War."