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.
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.
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.
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.
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.
