CB felt dejected when Lainey left with Barry Goldberg, her high-school sweetheart, after William Penn's talent show Saturday night. He headed into school that next Monday, dreading the notion of facing her again… but ironically, she couldn't wait to see him.

Lainey and Wilma throw a New Year's Eve party for William Penn's faculty, and everything goes off without a hitch - that is, until Lainey realizes she has feelings for CB.

C.B. becomes jealous when Jeff starts spending time with Coach Mellor. Meanwhile, Ephram suffers an injury.

Jeff returns to William Penn after his grandmother's funeral. All he wants to do is get back to his normal routine. However, C.B. and Coach Mellor know he still has some grieving to do.

Told from Emily's point of view. Emily turns to Lainey for help when Coach Mellor begins acting hostile towards Emily. Meanwhile, Logan discovers a football player at William Penn has a crush on him. Jeff does not appear.

Jeff and Emily hide the seriousness of their relationship while Logan and Ephram try to cover up the fact they fell asleep in Logan's room. Meanwhile, Coach Mellor schemes to get the basketball team a spot in the Thanksgiving Day Parade and turns to Beverly Goldberg for help.

Coach Mellor intervenes when Ephram is too scared to go to the Halloween Masquerade Ball with Logan. Meanwhile, after a rival school plays a prank, Jeff, C.B., Lainey, and Emily decide to get revenge.

Jeff and C.B. start a movie club at William Penn. When Jeff picks "The Sandlot 2", the club is divided on their opinions, which soon spreads throughout the whole school. Meanwhile, Lainey convinces Logan to purposely test Emily to make her feel like a parental figure.

Lainey decides to put on "High School Musical" at William Penn. Meanwhile, Jeff gives college tours to the high school seniors and begins regretting not going to college.

Erica's the one who figures out that Lainey's gone and fallen for CB.

Jeff is upset when C.B. is given the position of the new Academic Coach, so he decides to create his own team. An all-out academic war breaks out within the hallways of William Penn. Meanwhile, Lainey and Coach Mellor help Logan ask his crush to the school dance.

Taking place in 2000-Something, Jeff Longston is the new Algebra teacher at William Penn. His serious personality gets him off on the wrong foot. Meanwhile, in a homage to "One Tree Hill", Coach Mellor and Lainey scheme to get two former best friends on the basketball team get along