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This article examines the writings of short story theorists, Michael O’Toole, Monika Fludernik, Uri Margolin, Bruce Morrissette and John Gerlach, and analyses their findings through comparison with a number of experiments with viewpoint in my recently published short fiction collection Mr Jolly (2016). These experiments include utilizing second-person in order to understand its ability to exploit narrative indeterminacy, as well as other experiments with point of view in order to explore how various narrative modes can enhance dramatic engagement. Finally, the link between viewpoint and other narrative effects is demonstrated through the inclusion of a short story example from the collection.