His father, Herbert T. Gillis, wants Dobie to earn money by working at the family grocery store.
At the Bijou, something that Dobie sees in the movie makes him have a change of heart about cheating to win the Jackpot.
Dobie is in love with Thalia, but she keeps making eyes at wealthy, better-dressed Milton Armitage.
Dobie's brainy lab partner, Zelda Gilroy, says three surprising first words to him: "I love you".
Davey tells Dobie that to get the girl interested in him, he should pretend he's in a relationship with an older married woman.
Maynard's other friends, Riff Ryan (Tommy Farrell) at the record store and Charlie Wong at the ice cream parlor, start to feel the same way.
Maynard goes home and finds his father (Willis Bouchey) upset with him for the large phone bill he created.
Thalia thinks Dobie could become rich by being a popular singer like Elvis Presley.
Dr. Cligger (Harvey Stephens), a psychiatrist, is shopping in the store and Winnie thinks Herbert should talk to him about Dobie.
Some of his classmates tell Milton that Dobie has a good chance of winning with his man of the people style.
Dobie enlists the help of former school athletic legend Moose McCullough and they plan to stage a fight.
The poem gives Dobie the idea to become weak and pale to gain Thalia's sympathy.
The next day, some of the girl's tell Dobie they think it is wonderful that he's on a hunger strike for love.
Herm (Ryan O'Neal) and some of the guys think Dobie's faking it and tell him they'll be watching.
Math teacher, Mrs. Ruth Adams (Jean Byron), would like to see Dobie after class.
Ruth's husband Esmond (John Bryant) and her son Dan (Ron Howard) come by.
Thalia wants Dobie to go to Willoughby Hall, an exclusive eastern prep school, where all the rich influential kids go.
But when he finds out that Maynard pulled some strings and will be Dobie's roommate at the school, he changes his mind.
Whitney tells Dobie she doesn't want a guy that can think and she says she's now picked Maynard.
Unfortunately, Dobie didn't make a good first impression with her father, ex-navy man John Lomax (Harry von Zell).
Myrna's friend Betty Lou calls and John mentions that Dobie has joined the Navy.
John makes a phone call and then they go see Lt. Smedley (Robert Nichols) at the recruiting office.
Lt. Smedley says that 17 year olds can't join unless Dobie gets his father to sign a consent form.
Now Dobie doesn't have enough money to take Melissa to see The Kingston Trio this Saturday.
To secure the bank loan, Herbert has to get Dobie to be Mignonne's date for a party she's giving on Saturday night.
Dobie finds a way to hold the picnic in a pavilion, but then learns he can't sell the sandwiches there.
Daphne Root (Diana Millay) is upset with Chatsworth because he has never done a decent day of work in his whole life.
Meanwhile, Arabella tells her mother Edith (Margie Liszt) what a nice boy Dobie is and how much she likes him.
Sam visits Herbert and Winnie and tells them that he wants Dobie to stop seeing Arabella.
Jenny thinks that in order to get Herbert on their side, Dobie needs a job so he can support them when they're married.