The first half of the season explores Dobie Gillis' life as a senior at Central High School.

The rest of the season primarily centers upon Dobie and Maynard's misadventures in basic training, with a handful of episodes featuring the characters back in their Central City hometown while on leave.

The season originally aired Tuesdays at 8:30-9:00 pm (EST) on CBS from September 27, 1960 to June 27, 1961.

Dobie joins the school band just to be closer to Esme Lauterbach (Kathe Green).

Mr. Pomfritt, the band leader, will offer a prize to the student that writes the best original Jazz tune.

Zelda's written a Jazz tune and wants Dobie to pretend he wrote it and enter it in Mr. Pomfritt's music class contest.

A Newspaper Reporter (Jack Albertson) shows up to the grocery store and his photographer starts taking pictures.

Herbert wants to go fishing so Dobie has to cancel more time with Mason and she is not happy.

Herbert and Winnie overhear Dobie tell Mason he wants to use the money to buy his father something.

Mrs. Clarissa Osborne is so impressed that she wants to put Maynard on her TV station, KASH.

Maynard goes on the show "The Hot Seat" which is hosted by Henry R. Starbuck (Dan Frazer).

To question Maynard, Henry has brought in psychologists, Dr. Thaddeus Emmons, Dr. Otto von Schwering (John Banner) and Dr. Carlotta Kaggel (Winifred Deforest Coffin).

Maynard likes his new found celebrity and doesn't think what Dobie suggested is fair.

After the election, Dobie tells Maynard the name he wrote down on the paper wasn't the winner.

Two crooks, Willy Frymass (Joey Faye) and Alfred Montcalm (Milton Frome) are in the jail cell there and hear this.

Knowing that Maynard will be able to pay him back the next day, Herbert fronts him the money for the party.

Winnie wants to take Dobie to a touring art exhibit by Aristede Le Blanc (Marcel Hillaire) at the museum.

Winnie learns that Aristede has a daughter named Yvette (Danielle De Metz), who is Dobie's age.

Winnie would like Dobie to meet a girl of culture so she invites Aristede's family over for dinner.

Dobie mentions that the teachers are meeting with the School Board to discuss a pay raise.

That night Mr. Pomfritt tells the Board that the meeting will have to be postponed as all the other teachers have come down with the flu.

At the next Board meeting the parents vote to give the teachers a bigger raise than they requested.

Herbert bets Winnie that if she ever wins a contest, he'll let her mother and sister come to visit for six months.

Meanwhile, Dobie is interested in Jessica Tichborn who had been going out with school athlete Fast Freight McCurdy (Norm Grabowski).

But Jessica is tired of Fast Freight and his muscles and wants someone like Dobie now.

Dobie gets a letter saying he won a magazine contest and first prize is a date with glamorous movie starlet Merilee Maribou (Joyce Jameson).

When Jessica finds out about Dobie winning the date with Merilee, she no longer wants to see him.

It was a similar stormy night and Dobie, Maynard and Zelda were watching the grocery store.

At the police station, Chief Rosenbloom (Herb Vigran) is trying to find out where a Little Boy (Ronnie Howard) lives.

They give him a space helmet and a plastic ray gun to play with just as Maynard walks in.