In the annual teachers golf tournament, Jeff is finally going to win, but then discovers that Alice broke his laptop.

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.

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.

Jeff, who has the hots for co-worker Alice decides to try for another first date by asking her to the prom together as chaperones. His plans fail, though, as Alice brings a third party.

Alice falls for the testing guru Doug and so Jeff as to expose Doug. Dick has to help Tina to save her job at the school.

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.