Peasant Dobie Gillis would love to be a member of the Silver Spoon club, whose president is Chatsworth Osborne, Jr. Herbert tries to secretly help out by providing the club with free groceries. When Dobie finds out, he tries to take advantage of the club members as much as they are taking advantage of Dobie's Dad.

Dobie plans to work his way up from janitor to executive in the lumber business, and good girl Gloria is ready to stand by him--until the owner's daughter catches his eye.

Like the hero in the western High Noon, Dobie must face a bully by himself.

When Winnie goes away for two weeks, Herbert and Dobie happily let the dishes pile up and generally keep an untidy house, but must pay the consequences when Dobie hasn't a clean shirt to wear to his date.

Trying to impress an honest girl named Eloise, Dobie convinces his Dad to pay a parking ticket he already had fixed. But Herbert's attempts to pay arouse the suspicion of the police. And Dobie hasn't decided between truth-loving Eloise and devious Mona...

Maynard reunites with Edwina "Eddie" Kegel, except this time she's part of the Osborne family, and Chatsworth and Mrs. Osborne want Maynard to stay away from her.

When Maynard meets a modern day caveman, he is torn between being believed by his archaeology teacher and the dean or letting Ugh-Ug live in peace.

It's the obligatory drag episode! Dobie lies to Samantha about being rich, but when he and Maynard get work serving at a sorority party, Dobie will do anything to avoid Samantha seeing him there, including, well, dressing as a girl.

Dobie's latest girl, Caprice, convinces him to give up Maynard, supposedly for Maynard's own good, but that proves impossible when Maynard comes to live with the Gillises.

When it's discovered that Maynard has a better sense of smell than Charlie, the Basset Hound, he and Dobie go into business as private detectives. Then a greedy gal steals Maynard away from Dobie.

Professor Imogene Burkhart is putting on a show in class, the dances of an exotic island. When Maynard writes an article on it, he uses a provocative choice of words, causing parents to fear the bewitching Imogene Burkhart and her scandalous dance.

Others compliment Maynard on how honest he is. He takes it to heart, and decides to tell the brutal truth to all of them.

Dobie wants to go to Harvard to be near his latest gal, Giselle Hurlbut, even if it means cheating on Mr. Pomfritt's test.

Winnie named Dobie after a Nobel Prize winner, but Giselle wants him to change his name. Dobie is about to cooperate with Giselle, but then he gets an opportunity to meet with the man who so inspired his mother.

Miss Burkhart volunteers Dobie and Maynard to assist her at her program for troubled youth; however, it's Maynard the delinquent boys really relate to, and not her.

Thalia's back in town, and she wants Dobie to quit college and become a salesman.

Trying to impress a girl in his economics class, Dobie invests in eggs. But when he doesn't sell when he should have, he winds up with egg on his face and more eggs than the Gillis grocery store can possibly sell.

In Mr. Pomfritt's class, Dobie learns that married people are better off, so he decides to marry Zelda. Herbert and Maynard, each for their own reasons, are not too happy about this, and even Zelda is having second thoughts.

Maynard finds a soul mate in Edwina "Eddie" Kegel, a tomboy who shares all of his interests. Then, she suddenly starts to like being a girl...

To get away from Zelda, Dobie (and Maynard) stow away on a ship heading for South America. Little do they realize that Zelda has also stayed on board.

Herbert thinks selling his store will make him rich, so he showers Winnie and Dobie with gifts he can't afford.

Chatsworth wants Herbert to teach him how to be a real man, but his mother has other ideas, namely spoiling Herbert--and Winnie--with the rich life.

It's more politics, but this time it's Herbert T. Gillis running for office--with or without his son's support.

Dobie runs against Chatsworth for student council. Chatsworth seems more likely to win, as he has a group of folk singers backing him up, so Dobie also resorts to folk songs to promote himself. Meanwhile, Mr. Pomfritt watches on with a disapproving eye...

Between football, studying, and kids, star player Bronkowski is a mess. But Dobie, Maynard, and Herbert will rally behind him--to the point of all three taking turns taking Bronkowski's place on the field.

Maynard keeps losing the money for the class' Christmas dance, but what he won't tell them is he is giving the money to a poor Mexican boy and his family.

Mr. Pomfritt encourages Dobie with Robert Browning's line, "A man's reach should exceed his grasp." Dobie tries applying that in his quest for another new girl, even though Zelda warns him that, should he fail, he won't be able to crawl back to her anymore.

Dobie falls (literally) for a kind-hearted girl whose parents have come up with unusual rules for guys who want to date her. Dobie must share his date with Chatsworth, and then Maynard, or call it quits completely.

Dobie believes Maynard has stolen a substantial amount of cash from Mr. Pomfritt, and Mr. Pomfritt and Maynard believe that Dobie has stolen it. Can the real thief be found before Dobie and Maynard's friendship is destroyed?

Maynard has read headlines of the day, and fears the world will end. While Dobie tries to reassure Maynard that life will go on, Chatsworth takes advantage of Maynard's terror. Meanwhile, the class prepares a time capsule.

When Dobie innocently becomes enamored of Ancient Egypt, Herbert assumes he can blame a girl. Upon finding no girl in class, Herbert assumes Dobie has something going on with his thirty-five year old history teacher, Imogene Burkhart.

Maynard strikes it rich by providing companionship to girls missing their boyfriends--and the boyfriends trust their gals won't fall for Maynard! But Maynard has changed, and Dobie will do anything to get the old Maynard back.

Inspired by a lab experiment in heredity, Dobie convinces Zelda that their kids could turn out dumb, like him. Then he sets her up with Chatsworth. Zelda and Chatsworth seem happy together, and Dobie's finally got Zelda off his back, so why is he so miserable?

A law teacher encourages Maynard to sue when he injures his hand at the Gillis grocery store. Can Maynard go through with it without alienating his "second Dad" Herbert?

A new girl sets her sights on Dobie when she sees how a smart girl like Zelda wants him. But will this girl be able to live with herself when she sees how brokenhearted Zelda is?

Dobie and Maynard are discharged from the army--now what do they do? Dobie seeks his answers at S. Peter Pryor College--and it looks like he'll have Mr. Pomfritt as a teacher again, much to Pomfritt's dismay!