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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 is desperate for money so he can take Thalia to the dance, so he and Maynard hatch a plot to dishonestly win $100 at the Bijou Theater on Jackpot Night.

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.

Dobie forsakes poetry and sets to studying science so he can become a wealthy doctor and win Thalia's greedy heart. This episode introduces Zelda Gilroy and features her and Dobie's first meeting.

Brother Davey, home from college, gives Dobie some bad relationship advice.

Maynard receives his draft notice and Mr. Pomfritt and Dobie host a testimonial farewell dinner for him. This episode introduces Michael J. Pollard as Maynard's beatnik cousin Jerome.

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."

Dobie falls for Poppy Herming but his father must also win her approval

Dobie thinks everyone has forgotten his birthday.

Herbert T. Gillis finds himself in jail on Christmas Eve after being stripped of his holiday spirit and driven to desperation by his family and customers.

All Dobie wants is six dollars so he can take Thalia to the junior prom, but Dobie's Dad won't give it to him until Dobie admits he hates his father. A gentle satire on psychiatric trends of the day.

Carlos, the suave son of an Argentinian general, boards with the Gillis family and immediately wins the fickle heart of Thalia. Dobie and Maynard plot to sabotage his success.

Thalia persuades Dobie to run against Milton Armitage in the election for junior class president. With Thalia serving as campaign manager and Maynard running a dirty tricks operation, how can Dobie lose?

Thalia will give her love only to an athlete, so Dobie schemes to set himself up as a fearless fighter, Top Fist. But Milton Armitage, Dobie's rival for Thalia's fickle heart, calls Dobie's bluff and challenges him to a bout.

Inspired by a poem and the prospect of winning Thalia's heart, Dobie embarks on a hunger strike, evoking from his family and friends admiration, worry and even wrath.

Dobie falls in love with the beautiful and brainy Aphrodite, whose robust family of health-food-eating acrobats begin putting Dobie through rigorous training in anticipation of the day he'll join their family and their act.

Thalia wants Dobie to go to Willoughby Hall, an exclusive eastern school, and befriend the sons of wealthy bankers (an idea that also captures Mr. Gillis' fancy in a dream sequence). All Dobie wants is Thalia's love, but to win her heart he must get a 100 on his math test. To what depth will he sink for love?

Dobie becomes enthralled by the theories of Professor Dobkin, author of "The Power of Magnetic Thought," whose teachings promise to make him the "dominating male" that Thalia demands.

Dobie plots to make Zelda more appealing to other boys by spreading a rumor that Zelda's father is inheriting one million dollars.

Thalia attempts to teach Dobie the art of thinking, Maynard thumps out a jazz beat to "cogito ergo sum" on his school desk and new girl Whitney threatens to shake up the status quo.

As hard as he tries, Dobie just can't seem to get rid of Zelda Gilroy, the one girl he doesn't want but wants him. Zelda is aware of Dobie's failings, such as not being a very bright student and thus not having any future career prospects. Zelda compensates for that by mapping out their future: they will live on a farm after they get married so that Dobie will at least be able to provide food. In being a farmer, Dobie has to take biology class, with which Zelda will help him. Dobie agrees to take biology only because he knows that brainy Zelda has his academic best interest in mind and will help him. Dobie sees being a farmer as his only future hope, regardless of if Zelda is in that future. As usual, Maynard follows Dobie into biology class. Their first project is to examine the effects of hormones on chicken. One will be injected with female hormones, one will be injected with male hormones and the control chicken will get no injection. Three problems arise with their new arrangement. First, Mr. Gillis, who doesn't know that Dobie has chickens, keeps on hearing rooster crows, which he is made to believe is all in his imagination. Second, Dobie wants out of his arrangement with Zelda if only because he has met the pretty Imogene Burkhart, who he sees as a possible girlfriend/future wife. And third, Maynard is forced to give the chickens their injections. He believes that a 2 cc injection means a 2 cup injection.

Dobie lies about joining the navy to impress a girl's sea-minded father.

Seeing a financial opportunity, Thalia gets Dobie and his Dad mixed up with a shady dry cleaning operation. Will she clean up while they're hung out to dry?

Mr and Mrs. Gillis are persuaded to help with the Central High Student-Parent Betterment League's Capers, an amateur revue featuring acts of questionable talent.

To help his father's chances of securing a loan, Dobie agrees to date the banker's spoiled-brat daughter.

Dobie and Maynard strike out on their own and rent an apartment.

Thalia hatches a scheme for Dobie to sell sandwiches at the school picnic.

Chatsworth Osborne, Jr. agrees to assist the under-dressed Dobie and Maynard gain entry to his cousin Sabrina Armitage's black-tie soirée by having each fellow take a turn wearing his tux. Will their jig be up and their pants down?

Mr. Gillis dreads signing his will and suffers a nightmare of what his wife and sons would do with his store in his absence.

Dobie and Chatsworth compete for the affections of Daphne by setting to work to sell the most shoes in her father's shoe store.

When the Quimbys come to town and open a grocery store, Dobie competes with Chatsworth for Delphine's affections while Mr. Gillis competes with Mr. Quimby for the local grocery trade.

Maynard is smitten with Francoise, and to compete with the similarly smitten Chatsworth Maynard trades in his sweatshirt and jazz sides for a sport coat and tie, but will he agree to shave off his beatnik beard?

Dobie falls for a nurse and fakes having a serious illness to win her attentions, but the disease he and Maynard plucked from a medical book sparks a panic.

After getting into a bit with a disgruntled police officer over picking flowers in the park Dobie goes to visit his new date that just so happens to be the officer's daughter.

Dobie acts impulsively and proposes marriage to Zelda.

Dobie meets Gwyneth, a simple girl who despises money, until her kid sister begins dating 13-year-old Chrissie Tyler, who runs a lucrative babysitting racket out of Charlie Wong's ice cream parlor.

Dobie and a girlfriend take a baby-sitting job, but the Gillises suspect Dobie is secretly a father.