At Winslow High, located just outside Boston... Principal Harper grapples with seemingly nonstop dilemmas that spring up throughout the day.
Harper’s headaches mount when girls throughout school protest Lipschultz’s remarks by displaying their brassieres.
The school board considers Harper’s dismissal; tension erupts when the football team fears one of their own is gay; Harper pursues bullies on the school’s soccer team.
Lauren catches two student government candidates in a compromising position; a soccer team member is devastated when Harper refuses to sign his Magna Club application; teachers are lampooned during a charity show.
As the Thanksgiving holiday approaches... a fourteen-year-old girl asks Lauren for advice on contraception, and Harper comes under fire for having taught a student self-defense maneuver.
When a teacher suddenly drops dead, his widow claims he was having an affair with a student; a student faces expulsion after he spits on Lauren; a teacher uses a paddle to discipline her class.
A sixteen-year-old girl considers breast enhancement surgery; Lipschultz discovers an unflattering cartoon on Sheryl’s website; Senate acts as a faculty sponsor for a student chapter of the NRA; Guber’s brother sets Guber up on a blind date.
As Christmas approaches... Buttle has a torrid affair with a young woman he met in a coffee shop; a student spikes Lipschultz’s coffee; police recover a human foot from a locker; Senate intercedes when a student attempts to parent his siblings.
Police search in the school for a student who shot a man at a restaurant.
News of Buttle's relationship with a student hits school computers.
Kevin wants to ask out Marilyn; Harper's shocked by a cheerleading routine.
Harry rescues a student; Kevin and Guber have a confrontation; Lauren provides support to a student.
Kevin seeks legal help in the wake of a teacher-student affair.
Guber must find replacements quickly after six teachers quit.
Harper lands in another teacher-student scandal.
Lauren seethes over an event captured by a security camera.
Harper confronts Senate about his knowledge of Tyrone's gang life.
Marla shows her students what life might be like without an education.
A student who once drafted a kill list threatens a girl who turned him down for a prom date.
The daughter of Harper's new girlfriend becomes rebellious at Winslow High.
Marla has concerns about a prom date between a senior and a freshman.
A father wants his home-schooled son to go through Winslow High's graduation.