When Principal Durbin's wife kicks him out of the house, he crashes with Jack, making it difficult for Jack to navigate his sexually charged friendship with his ex-girlfriend; meanwhile, Jack's students plan to frame Miles for a crime.
When Jack learns that his dead mother had a lover named Brandon, Jack becomes furious and sets out to destroy the old man; the students must take care of simulated babies for health class; and Stef is asked out by Dale, the janitor.
When Victor's parents go out of town, Jack uses their house to host his ex-girlfriend's fundraising gala, hoping to impress her and take down her boyfriend, Chase; meanwhile, Jack's goody-goody students have a party in the basement.
When Jack's book is rejected by multiple publishers for being too dark, he must decide if he will sell out and write a much sunnier, more marketable book; meanwhile, Stef recruits Principal Durbin to be her bestie after Mary offends her.
It's parent-teacher day at Whitlock High, and Jack falls hard for Colin's mom, but his date with her is derailed when Colin shows up and spoils their fun; protests erupt after Principal Durbin caves to a parent's complaint about nudity in art class.
Jack is tired of taking the bus to NYC for dates, so he lowers his standards and reluctantly joins Michelle, Stef and Mary for a night out at the bar to meet local women; Helen fills in for Principal Durbin on the morning announcements and kills it.