The next pair of Archetypal Characters are the Sidekick and the Skeptic, who represent the conflict between confidence and doubt in the Story Mind.

The Sidekick is the faithful supporter. Usually, a Sidekick attaches itself to the Protagonist. Sometimes, however, it may be a supporter of the Antagonist. This gives a good clue to the way Dramatica sees Overall Story Characters: The purpose of the Sidekick is to show faithful support. That does not decide who or what it supports, but just that it must loyally support someone or something. Other dynamics of a story control whom the Sidekick supports to make the story's argument.

The Skeptic balances the Sidekick.

The Skeptic is the disbelieving "opposer." Where the Sidekick has faith, the Skeptic disbelieves; where the Sidekick supports, the Skeptic opposes. The line from a song, "Whatever it is, I'm against it," fittingly describes the nature of the Skeptic. In the Story Mind, it is the function of the Skeptic to note the indicators that foreshadow failure. In contrast, the Sidekick notes the indicators that point to success.

The interactions between Sidekick and Skeptic describe the Story Mind's consideration of the likelihood of success.