Willis' classmate Larry wants his help to get a date with a girl at school, so Willis gets Kimberly to assist him, but Larry falls in love with her.

Arnold is tricked into playing Romeo opposite Lisa's Juliet in a class play. Although Arnold works hard for his performance, Lisa is overcome with stage fright and Arnold has to help her out.

Arnold struggles to find a subject for the school's journalism contest. When he discovers that drugs are being sold at the school, he sets up a meeting with the dealer so he can write about it. First Lady Nancy Reagan speaks to his class about the dangers of drug use.

Mr. Drummond trades rooms with Willis while he is busy studying for exams. However, sharing a room with Arnold leads to discomfort for Mr. Drummond, while Arnold finds much humor at his expense.

When Arnold faces a streak of bad luck, he is given a lucky cricket to help him out. Arnold's fortunes soon change and he tries to use the cricket to get out of trouble with the Gooch, but the cricket escapes and Arnold has to come up with a back-up plan.

Kathy transfers to Arnold's school and is treated very poorly because of her disability. When she becomes hall monitor, she rules with an iron fist and doles out demerits to everyone except Arnold. When Arnold feels the heat from his friends over getting away with everything, he tries to get Kathy to lighten up, but she refuses and gets tough with Arnold instead.

Kimberly impresses professional skater Dorothy Hamill with her ice skating and is taken under her wing. However, Kimberly is overwhelmed by the hard work it takes to become a professional skater and devises a way out.

Drummond and Mr. Ramsey learn the truth about Mr. Horton, the seemingly friendly bicycle shop owner with a very sinister side. It soon becomes a race against time to get details out of Arnold after learning that Dudley is about to become Mr. Horton's latest victim.

Arnold and Dudley become friends with the owner of a local bicycle shop named Henry, unaware that he is a pedophile looking for his next victim.

Kimberly stops working at Mr. Drummond's company and takes a job at a burger place, but is sexually harassed by her boss. When he finds out that Kimberly's family is wealthy and live on Park Avenue, he apologizes and ends up becoming romantically involved with her, for the purpose of advancing in her dad's company. Arnold soon learns what he is up to and tells Kimberly.

Mr. Drummond sneaks around behind the kids' backs while dating his tax attorney and invites her over to the apartment while the rest of the family's away, but when they return early, Mr. Drummond has to explain her presence.

Willis is forbidden to go to a party when Mr. Drummond finds out there will be drinking there. After Willis disobeys and is caught, he decides to move in with Jerry and ends up in a car crash.

Arnold helps out a street corner Santa Claus, who takes advantage of Arnold and his family's kindness by robbing the Drummonds.

Arnold, Kimberly and Willis get jobs at Mr. Drummond's company, but when Willis finds out that minority kids don't have the same opportunities at employment, he goes undercover to see for himself and goes too far.

Arnold's confrontation with the son of the new building manager leads to Mr. Drummond punching the manager in the face and almost gets the family thrown out of the building.

Arnold takes it hard when he hears his mother's voice again on an old audio tape and pretends to lose the tape permanently.

When Kimberly submits a candid picture of Arnold with his butt exposed to a photo contest, he is infuriated and demands that Kimberly withdraw it, but the picture remains in the contest by mistake and almost ruins Arnold's chances of winning the class election.

Willis wears a fake mustache to get into a club and lands a date with the waitress.

A substitute teacher makes life hard for Arnold and Dudley, so they try to make things difficult for him in return. When one of their pranks leads to Arnold getting hit by accident, they go to the principal and tell him that it was done on purpose, which gets the teacher in trouble and nearly gets him fired until Arnold and Dudley come clean about what really happened.

Willis tries to negotiate peace between two rival groups of students at his school, but when one of the students, Larry, has his stuff stolen, Willis becomes the prime suspect and is forced to get a gun to protect himself.

After learning that Joey, a new boy at his school has no friends, Arnold takes it upon himself to befriend him and take him home to meet his family. While there, he convinces Willis to become a "big brother" to Joey. As a result, everyone at the Drummond household take such a shine to Joey, that Arnold becomes jealous and decides to run away.

Arnold offers to help his bashful buddy Dudley win the affections of a young lady-- who falls for Arnold instead.

Kimberly decides to transfer to Willis' school and gets into a confrontation when she tries to join the all-male swim team. The Drummonds get a new housekeeper named Pearl.

Arnold tries to outdo Willis on an arcade game, but constant playing takes a toll on his schoolwork.