Oliver's parents try to join a beach club, which is fine with Oliver, because Bonnie, a talented swimmer who Oliver has a crush on goes there. Oliver tries to impress her, but unfortunately, he doesn't know how to swim.
Oliver's parents go visit a old college friend, whom he hasn't seen in ages, leaving Oliver and Ted alone at home for the first time.
When jumping the legendary Great North Wall at school, Oliver injures a black student, making it appear that he's racist.
After destroying Michael's father's nudie magazine, Oliver and Michael go out of their way to replace it. Meanwhile, Ted falls in love with a model in one of those magazines.
Oliver cheats his way into the Geography Bee as a way to finally beat Susan Brotsky, but after confessing to his teacher, his teacher allows him into the competition, because he also wants Oliver to beat Susan.
Oliver takes ballroom dancing classes because he wants to be like the dancer Fred Astaire, but when he realizes he has two left feet. Charlotte and Jerry compete in a series of charades with another married couple.
After finding out that Joyce's parents are getting divorced, Oliver fears the same fate for his own parents and when Jerry accuses Charlotte of adultery, this just reassures Oliver.
Oliver begs his parents to get him a dog, but after finding the dog is too much to handle, he tries to give him up. Ted feels insecure after a girl turns him down.
Ted calls dibs on the new Swedish foreign-exchange student named Elke, but Oliver tries to find a way around the rules of dibs. Jerry and Charlotte go to an old club they used to hangout as teenagers, but are shocked to find out that it's turned into a marijuana-invested nightclub.
A horrible rumor about Oliver circulates the school after he spilled soup all over himself. Ted must play the piano at Jerry's Aunt's funeral.
Charlotte feels lonely when Oliver goes to work with his dad, so she asks Oliver's friend Joyce if she wants to be her "daughter" for a day. Oliver learns that his fathers dentist job isn't all that it is cracked-up to be.
Oliver tries to get revenge on a comic-book company, after ordering a pair of x-ray specs, which turned out to be a scam.
Jerry and Charlotte gets tickets to see John F. Kennedy.
Oliver tries to make amends with the school bully by allowing him to date Joyce. The president of the tenants' association asks Charlotte to remove a door knocker that Olive made in school, but Charlotte decides to get back by running against him in the upcoming tenants' association election.
Jerry invents "The Disposa Toothbrush", but finds out nobody wants his invention. Oliver finds out that his grades were low only because his old teacher was punishing him.
Once again out-shined by his neighbor's party, Jerry plans to get a celebrity to perform at his upcoming bash, and Oliver, along with Ted, suggests he gets Buddy Fontaine. After discussing the idea with Buddy, Oliver finds out he doesn't plan on showing up. With the party so close, Oliver and Ted must find someone better, and fast, before their dad makes a fool of himself.
Oliver develops a crush on Joyce, so he decides to form a band in order to impress her. Jerry has Charlotte fill in at his dentist office, after his assistant is injured.
When Oliver gets invited to his first "make-out" party, Ted gives him advice on what to do. Meanwhile, Charlotte tries to run for President of the Tenants Association.
Ted tries to toughen up his dad after he finds out he throws like a girl.
It's picture day, and Oliver decides to wear a super-hero costume in protest, because he can never take good pictures. Principal Shriner gets upset, and gives him the choice of expulsion, or see a psychiatrist. Meanwhile, Ted tries to stop Elke on going on a second date with his baseball coach.
In order to get the kids at school to like him, Oliver tries out for the school talent show. Meanwhile, Charlotte doesn't like her anniversary present from Jerry - a fallout shelter.
Charlotte takes the family on a vacation to the Catskill Mountains in order to spend more time with them, but the rest of the family aren't too thrilled about it.
After taking a trip to Coney Island with his family, Jerry fights with his neighbor over a parking space, causing a big feud. Meanwhile, Oliver gets a job as a paper boy, and learns that it is harder than it looks.
Joyce convinces Oliver to babysit for her, but when Oliver continues to babysit on his own, it appears he has taken all of her business away.
The owner of the local sports store wants Ted to date his daughter. Ted is hesitant, but after being offered whatever he wants in the store, Ted decides to go on a date with her.