The Many Loves of Dobie Gillis (1959)

Dobie and Maynard conspire to rig the raffle at the local movie theatre so that Dobie can win enough money to take Thalia to the prom.

Dobie competes with Milton Armitage to see whose wardrobe can impress Thalia the most.

Thalia urges Dobie to become a doctor, but he meets Zelda Gilroy and learns about the scientific concept of propinquity, the psychological tendency for people to form relationships with those whom they encounter often.

Dobie's older brother Davey convinces him to invent an affair with a married woman to impress a new girl in school.

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.

After a throat operation, Dobie can sing better than Milton, thus attracting Thalia.

Dobie tries to earn $6 to take Thalia to the Junior Prom.

Before the big football game, Dobie hatches a scheme for winning by stealing the opposing mascot.

Dobie is up against Milton to be leading man in a school play.

Dobie falls for Poppy Herming but has to win her father's approval too.

Dobie thinks everyone has forgotten his birthday.

Mr. Gillis is driven crazy by all the Christian celebrations, and almost spends the holidays in jail.

Herbert seeks free advice from a child psychiologist.

Mr. and Mrs. Gillis take in a young and handsome border from South America.

Dobie runs against Milton for junior class president. Thalia is Dobie's campaign manager.

Dobie becomes Top Fist by knocking out the legendary Moose. Milton tries to gain the title and Thaila's affections by challenging Dobie.

Dobie goes on a hunger strike until Thalia agrees to be his.

Dobie falls for trapeze artist Aphrodite Millican,.

Thalia talks Dobie's parents into sending him to Willoughby prep school.

In order to win Thaila from Chatsworth, Dobie reads a book on mental power so he can be the dominating man Thalia wants.

Dobie and Maynard are puzzled when a rumor they spread about Zelda inheriting a fortune seems to become reality.

Thalia tries to educate Dobie in logical thinking.

Maynard gives a chicken an overdose of growth hormones as a biology class project .

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

Dobie, Maynard, and Thalia capture a crooked dry-cleaner who had almost conned them before.

Dobie and most of his friends reluctantly participate in a talent show.

Doblie's dad wants him to romance a banker's daughter so he can get a loan.

Dobie wants to prove he's grownup, so he moves into a small apartment with Maynard.

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

Dobie, Maynard, and Chatsworth must all share the same tuxedo to get in to a black-tie party at the Armitage mansion.

Herbert worries about what will happen to the store after he's gone.

Dobie and Chatsworth complete for the attention of a shoe store owner's daughter in order to get a job at the store.

Dobie's newest girlfriend's father happens to be opening a new grocery store. Mr. Gillis tries to spy under the name Fred C. Dobbs.

Maynard falls for a French girl and shaves off his goatee.

Dobie falls for an older nurse and feigns a disease so he can be near her.

Dobie's new date's father turns out to be a cop with whom he had a disagreement about picking flowers in the park.

A discouraged Dobie finally gives up on finding his dream girl and agrees to marry Zelda.

Dobie finds a girl who doesn't care about money, until her younger sister starts going on finance dates with a richer boy.

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