When Stan realizes that he might never fulfill his dream of becoming a Best Man, he convinces his last single friend, Principal Lewis to marry the school’s Superintendent and to choose him as his Best Man. Stan invites Lewis’ old friend from prison to the wedding, only to discover a secret that could prevent the wedding from happening at all. Meanwhile, Roger finds the perfect pair of shorts, and an encounter with Ricky Martin makes him question his self-confidence.

Hayley makes Jeff get a friend to add some mystery to their relationship but gets more mystery than she bargained for. Francine attempts to grow the world's longest fingernails.