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.

Jack receives an offer from Miles' publisher to write a book of feel-good philosophy that could be his ticket out of Toledo. Durbin accidentally sets off an emotional firestorm when he reveals that while Stef chose Mary as her emergency contact, Mary chose Michelle.