Lainey has a difficult choice regarding her relationship with Barry and her friendship with CB. Meanwhile, Coach Mellor is put in a tough parenting position when Toby is invited to prom as a freshman by a senior.

Smitten with environmental consultant Paloma, who was hired to oversee William Penn's Earth Day activities, CB's feelings may change when he learns she wants to stop an important construction project at the school. Meanwhile, Wilma gets a surprise after convincing Lainey that yearbook superlatives are not important.

Coach Mellor deals with jealousy issues after learning Julie is friends with a handsome doctor. Meanwhile, Glascott appoints CB to be substitute principal after his surgery, but needs Lainey to solve a problem with the mean girls of William Penn that he can't.

With some encouragement from Coach Mellor, Lainey reunites with her mother. While inspired by the film "Good Will Hunting," Wilma adds a new, unorthodox addition to the robotics Club. 

Cool parent Greg distracts CB from being a good teacher to help his son Weasel receive extra credit, while former Principal Ball is upset at Principal Glascott when he approves the use of Ball's parking spot as a community garden.

While preparing students for the school's show choir, Lainey realizes Wilma might be a better singer than her and gets competitive. Meanwhile, Coach Mellor and Aunt Julie fight over how to parent Toby.

Wilma steps in to help CB move on from Lainey with help from Coach Mellor, while Lainey learns she has unresolved issues from her past when mentoring a student.

In honor of Valentine's Day, Principal Glascott throws a "dating game" based on the show "Singled Out" where Lainey uses the opportunity to figure out her feelings. Meanwhile, Felicia is having body-image issues and Coach Mellor throws a workout camp to help her self-esteem.

The hit film has love on everyone's brain, and Lainey has a realization about CB. Meanwhile, Principal Glascott uses the season's bad football team to teach Coach Mellor how to be both a good winner and a good loser.

Principal Glascott and Lainey struggle to agree on what is an appropriate dress code, while Coach Mellor struggles with his relationship with Julie as she does not enjoy sports like he does.

Wilma encourages Ronnie to pursue his dreams of being in a boy band but goes too far when a music video gets out for all of William Penn to see. Meanwhile, the school hires Aunt Julie as the new school nurse which quickly affects her relationship with Coach Mellor.

CB hopes getting Lainey a Beanie Baby for Christmas will show his true feelings for her, but it doesn't go as planned. Meanwhile, Principal Glascott tries to convince Felicia that she needs to participate and sing a song in a Kwanza play he has written for the students.

Learning he's not into baseball cards, Coach Mellor encourages Toby to be competitive in CB's Pokemon Club and becomes an overbearing sports-type father. Meanwhile, Lainey supplements her salary as a teacher by working at the local video store and learns an important lesson.

CB celebrates Thanksgiving by having all of William Penn rally around him after a cooking incident at his house, while the alumni faculty football game brings out the competitive sides of Wilma and Coach Mellor.

Coming off the musical success of "Rent" last year, Lainey is asked to direct a school production of "The Lion King," but she fears she can't top herself. Meanwhile, Coach Mellor's athletic records may soon be broken, so he must find a way to keep his name in the spotlight.

Coach Mellor is excited to celebrate Halloween in a couple's costume with Julie, but his plan might be derailed by Principal Glascott's faculty-parent dating rules. Meanwhile, CB uses "The Blair Witch Project" to attempt to scare the students into not tormenting each other during the school's annual Halloween parade.

When a bad flu epidemic hits William Penn, Coach Mellor is sent to his sick bed and Principal Glascott must step it up as the wrestling coach with the Jenkintown Cup on the line. Meanwhile, Lainey thinks she can easily pass a class taught by CB, yet it's anything but.

Hoping to improve the football team's chances at winning the title, Coach Mellor and Principal Glascott recruit star soccer player Felicia to kick field goals. But soon, she is treated like one of the guys, which affects her relationship with fellow player Reza. Meanwhile, CB chaperones an overnight ski trip and hopes to get in some quality time with Lainey but is constantly thwarted by socially awkward Tom Scott.

After watching the classic film "Rudy" in CB's class, William Penn student Toby wants to play football. Since Toby isn't very good, Coach Mellor hopes to encourage him by telling his players to let Toby score a touchdown in a scrimmage, but the plan goes awry. Meanwhile, Principal Glascott suggests Lainey find a girlfriend to give her advice on life, so she tries to befriend Wilma to attend a Boyz II Men concert together.

Overwhelmed by the love she has for Barry, Lainey wants Coach Mellor to have the same feelings for someone special, which proves challenging. Elsewhere, Principal Glascott is unsure of how to handle difficult librarian Dr. Ness, and CB and Wilma disagree on what should be done with him.

The summer is over. On her first day back, Lainey is excited to be back at William Penn Academy, but Mellor warns her that being a pal to her students is not a good idea. Meanwhile, Principal Glascott introduces the newest science teacher to the faculty, but CB is skeptical of her no-nonsense approaches.