E1 - Caper at the Bijou
!Sep 29, 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.
E2 - The Best Dressed Man
!Oct 6, 1959
Dobie competes with Milton Armitage to see whose wardrobe can impress Thalia the most.
E3 - Love is a Science
!Oct 13, 1959
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.
E4 - The Right Triangle
!Oct 20, 1959
Dobie's older brother Davey convinces him to invent an affair with a married woman to impress a new girl in school.
E5 - Maynard's Farewell to the Troops
!Nov 3, 1959
Maynard gets drafted.
E6 - The Sweet Singer of Central High
!Nov 10, 1959
After a throat operation, Dobie can sing better than Milton, thus attracting Thalia.
E7 - Greater Love Hath No Man
!Nov 17, 1959
Dobie tries to earn $6 to take Thalia to the Junior Prom.
E8 - The Old Goat
!Nov 24, 1959
Before the big football game, Dobie hatches a scheme for winning by stealing the opposing mascot.
E9 - Dobie Gillis: Boy Actor
!Dec 1, 1959
Dobie is up against Milton to be leading man in a school play.
E10 - It Takes Two
!Dec 8, 1959
Dobie falls for Poppy Herming but has to win her father's approval too.
E11 - Dobie's Birthday Party
!Dec 15, 1959
Dobie thinks everyone has forgotten his birthday.
E12 - Deck the Halls
!Dec 22, 1959
Mr. Gillis is driven crazy by all the Christian celebrations, and almost spends the holidays in jail.
E13 - Couchville, USA
!Dec 29, 1959
Herbert seeks free advice from a child psychiologist.
E14 - The Gaucho
!Jan 5, 1960
Mr. and Mrs. Gillis take in a young and handsome border from South America.
E15 - The Smoke-Filled Room
!Jan 12, 1960
Dobie runs against Milton for junior class president. Thalia is Dobie's campaign manager.
E16 - The Fist Fighter
!Jan 19, 1960
Dobie becomes Top Fist by knocking out the legendary Moose. Milton tries to gain the title and Thaila's affections by challenging Dobie.
E17 - The Hunger Strike
!Jan 26, 1960
Dobie goes on a hunger strike until Thalia agrees to be his.
E18 - The Flying Millicans
!Feb 2, 1960
Dobie falls for trapeze artist Aphrodite Millican,.
E19 - Room at the Bottom
!Feb 9, 1960
Thalia talks Dobie's parents into sending him to Willoughby prep school.
E20 - The Power of Positive Thinking
!Feb 16, 1960
In order to win Thaila from Chatsworth, Dobie reads a book on mental power so he can be the dominating man Thalia wants.
E21 - Dobie Spreads a Rumor
!Feb 23, 1960
Dobie and Maynard are puzzled when a rumor they spread about Zelda inheriting a fortune seems to become reality.
E22 - Love is a Fallacy
!Mar 1, 1960
Thalia tries to educate Dobie in logical thinking.
E23 - The Chicken from Outer Space
!Mar 8, 1960
Maynard gives a chicken an overdose of growth hormones as a biology class project .
E24 - Dobie's Navy Blues
!Mar 15, 1960
Dobie lies about joining the navy to impress a girl's sea-minded father.
E25 - Taken to the Cleaners
!Mar 29, 1960
Dobie, Maynard, and Thalia capture a crooked dry-cleaner who had almost conned them before.
E26 - That's Show Biz
!Apr 5, 1960
Dobie and most of his friends reluctantly participate in a talent show.
E27 - The Prettiest Collateral in Town
!Apr 12, 1960
Doblie's dad wants him to romance a banker's daughter so he can get a loan.
E28 - Live Alone and I Like It
!Apr 19, 1960 - 30m
Dobie wants to prove he's grownup, so he moves into a small apartment with Maynard.
E29 - The Big Sandwich
!Apr 26, 1960
Thalia hatches a scheme for Dobie to sell sandwiches at the school picnic.
E30 - Soup and Fish
!May 3, 1960
Dobie, Maynard, and Chatsworth must all share the same tuxedo to get in to a black-tie party at the Armitage mansion.
E31 - Where There's a Will
!May 10, 1960 - 30m
Herbert worries about what will happen to the store after he's gone.
E32 - Put Your Feet in Our Hands
!May 17, 1960
Dobie and Chatsworth complete for the attention of a shoe store owner's daughter in order to get a job at the store.
E33 - Competition is the Life of Trade
!May 24, 1960
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.
E34 - The French, They Are a Funny Race
!May 31, 1960 - 30m
Maynard falls for a French girl and shaves off his goatee.
E35 - The Unregistered Nurse
!Jun 7, 1960
Dobie falls for an older nurse and feigns a disease so he can be near her.
E36 - The Long Arm of the Law
!Jun 14, 1960 - 30m
Dobie's new date's father turns out to be a cop with whom he had a disagreement about picking flowers in the park.
E37 - Here Come the Groom
!Jun 21, 1960
A discouraged Dobie finally gives up on finding his dream girl and agrees to marry Zelda.
E38 - A Taste of Lobster
!Jun 28, 1960
Dobie finds a girl who doesn't care about money, until her younger sister starts going on finance dates with a richer boy.
E39 - Rock-A-Bye Dobie
!Jul 5, 1960
Dobie and a girlfriend take a baby-sitting job, but the Gillises suspect Dobie is secretly a father.
