After initially trying to sabotage him, CB works with Barry and the JTP to help him win back Lainey's heart. Meanwhile, Glascott faces removal as principal after a prank damages William Penn Academy.

When CB finally gets the courage to tell Lainey that he has feelings for her, Dr. Barry Goldberg returns, derailing his big romantic reveal. Meanwhile, Glascott discovers that he can't make every teacher like one another after his plan with the school's staff goes awry.

Lainey and CB encourage a rebellious student radio club until a rogue DJ starts spreading rumors about them. Mellor takes umbrage when Glascott tries to change the school's mascot, so as a result, Mellor tries to get the school on board with a competing mascot.

As the new cheer coach, Lainey wants to bring the William Penn cheer team into the competitive competitions of the 90s, but she runs into push-back from Mellor and the football team. Meanwhile, CB and Glascott are at odds on how to help students resolve their problems, so they create a special kind of club.

Lainey encourages Glascott to trust his niece and let her get her driver's license, only to find Felicia isn't trustworthy. CB and the student "Star Wars" club bring Mellor along to the premiere of "The Phantom Menace," but Mellor's thoughts on the movie cause the club to dissolve.

When her high school reunion is held at William Penn, Lainey tries to hide her teaching job from old classmates, pulling a "Romy and Michele" lie with the help of Erica Goldberg and CB. Meanwhile, Mellor's distraught to learn his star athlete alum, Ruben Amaro Jr., sees Glascott as more of a mentor than Mellor.

After two students show up to school dressed in backward clothes, a la Kris Kross, Lainey tries to get kids to conform to social norms to protect them from ridicule while CB encourages them to embrace their uniqueness. Meanwhile, Principal Glascott struggles to say no to his teachers and disappointing his friends, so he enlists the help of Mellor to lay down the law.

When Lainey starts to teach the easy A course for jocks, Coach Mellor challenges her to expect more from his athletes. After CB points out Felicia needs to beef up her resume for college, Glascott bribes his niece to run for class president.

After Mellor tells Lainey that sports are king at William Penn, she sets out to put on the Broadway hit musical "Rent" to show Mellor the arts are just as important as athletics. Meanwhile, Glascott and CB struggle to modernize the school's outdated boy's health education program.

Coach Mellor is cracking down on cheating, which leads him to take on the failing mathletes for the upcoming Math Olympiad. Meanwhile, Lainey helps CB deal with a challenging student.

Lainey and Glascott encounter an overbearing parent and enlist the help of Beverly Goldberg. Mellor realizes he might want to start a family and be a father after CB shows him how to care for confiscated Tamagotchis.

Hoping to gain respect among her colleagues at school, Lainey comes up with a misguided plan to give an awkward and insecure student a full makeover. Meanwhile, Principal Glascott and Coach Mellor take friendly competition to a new level when they are both romantically interested in the math teacher.

It's 1990-something, and since Lainey still hasn't achieved rock ‘n' roll greatness, she returns to William Penn Academy as the new music teacher. Lainey has a hard time adjusting to being an authority figure, but she realizes she might not be so bad at it when she discovers a kindred spirit in Principal Glascott's niece, Felicia. Meanwhile, Coach Mellor struggles with Michael Jordan's influence on modern-day basketball.