When Jack is attracted to a student’s mother at a parent-teacher conference, he feigns interest in her son, Colin. A group of parents complain to Principal Durbin when they notice a piece of controversial student art from Mary’s class.
Jack reluctantly agrees to go out on the town with Mary, Stef and Michelle. However, his superiority complex proves difficult for the women of Toledo to overcome. Principal Durbin feels threatened when Helen fills in for him on the school’s video morning announcements.
While Principal Durbin struggles with budget cuts, Jack discovers his students pity him – so he rallies, making a splash at the school bake sale and getting kicked out of the bookstore for life.