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.

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.