Everyone gangs up on Alice when Jeff tries to make her jealous by hitting on the new substitute teacher and Calvin and Dick try their best to ensure that Alice doesn't get made faculty chair.
The principal of the school Emma Wiggins, and teacher Mitch, are enjoying watching Jeff panic when his attempt to play matchmaker for Calvin gets him in trouble with the Concerned Parents Association.
It's the yearly schoolympics in which Filmore High competes against town rival Caulfield Prep. They're trained by Jeff, which impresses Alice, until she learns a secret.
It is the annual online golf tournament and this year, Jeff is finally going to win but unfortunately he discovers Alice inadvertently broke his laptop. He turns to the faculty lounge computer and discovers Principal Wiggins has already claimed it for the day. Desperate, Jeff realizes that Calvin is directing a new play, so he concocts a plan to oust Calvin from his role as the director and tries to convince Principal Wiggins she would be the perfect choice.
Initially, Jeff is delighted to discover that Alice shares his derisive views about his nemesis, the perfect and handsome testing guru Doug. But that soon turns to dismay when she falls under his charms, and in attempts to "win" her back by exposing Doug as a fraud, Jeff and Calvin are caught in a compromising situation. Meanwhile, Dick makes a surprising and kind gesture to help Tina save her job as a teacher at Filmore High.
When Alice volunteers to chaperon this year's prom, Jeff seizes the opportunity to have a "first date" with Alice, so he also volunteers and suggests they go together. But his plans for a romantic evening goes from bad to worse when Alice invites a third party to join them. Meanwhile, Calvin gives Dick pointers on writing the senior farewell speech.