When Dennis becomes friendly with the Wilsons' house guest, a little Chinese girl, Margaret becomes jealous of Dennis's attention to the Wilsons' visitor.
Believing that Mr. Wilson is broke, Dennis goes all out to help his friend. This includes buying groceries for the Wilsons and leaving them on their doorstep; and putting on a show with his friends, using the admission fees to make money for Mr. Wilson.
Mr. Wilson wants to interview several gypsies for an article he's writing, but the gypsies are suspicious of outsiders. So he disguises himself as a gypsy in order to meet with them.
Dennis, along with his parents and the Wilsons, visits the San Diego Zoo to bring back a chimpanzee for their town zoo. However, the chimp causes a ruckus at the motel where they are staying overnight.
While still in San Diego, the Wilsons receive a visit from their nephew, Ted, a young sailor. When Dennis and Mr. Wilson get stuck in back of a laundry truck returning to the Naval base, their attempt to escape leads to the confusion of Mr. Wilson's being mistaken for an expected demolitions expert.
John Wilson has taken over writing the advice column for the local paper. However, complications arise when he unwittingly gives advice to two women - Miss Cathcart and Miss Tarbell - who are out to catch the same man, Sergeant Mooney.
Mr. Wilson has written a book about his eccentric Uncle Ned. But Uncle Ned thinks the stories in the book are incorrect, and refuses to sign a release for it to be published.
Dennis and his classmates eagerly participate in a "Junior Astronaut" savings-stamp program. The child who buys the most stamps will win a trip to Cape Canaveral to meet an astronaut.
John Wilson pretends to be sick in order to avoid Dennis. However, Dennis is seriously worried by Mr. Wilson's "illness", and spreads the word around town, leading to several concerned visitors.
Dennis is curious about what "falling in love" means. And the fights and reconciliations of three couples - his parents, the Wilsons, and a teenage couple - only makes him more confused.
When Dennis is appointed by the mayor to go to Washington, DC to ask their state senator to make the local forest a national park, Mr. Wilson believes his own Washington contacts can help.
Stretch Nichols, the school basketball team's star player, quits the team after being teased about his height and worn-out clothes one time too many. A sympathetic Dennis persuades Mr. Quigley to help by buying Stretch new clothes and giving him an after-school job, so that Stretch will feel better about himself and rejoin the team in time for the big game.
When Dennis sees Mrs. Wilson knitting booties (for Mr. Wilson's golf clubs), he jumps to the conclusion that the Wilsons are about to have a baby, and innocently spreads the word all over town.
In order to claim a prize, Mr. Wilson must make good on his claim that he has four sons. So he recruits Dennis and three of Dennis's friends for the roles.
Concerned that Eloise will be destitute if he should pass away suddenly, John Wilson hopes that his Aunt Emma will leave her money to him, so that he can in turn provide for Eloise. However, when Aunt Emma and Dennis become friends, Mr. Wilson fears that Dennis will inherit Aunt Emma's money instead.