This essay examines the relationship between sceptical attitudes and religious belief in David Hume’s Dialogues concerning Natural Religion. Understanding Hume’s thoughts on scepticism is one of the most important – if not the most important – keys to unlocking his thoughts on the legitimacy of reasoning in mathematics, science and philosophy. Intense controversies swirl around his explicit arguments and analyses of sceptical themes in his A Treatise of Human Nature and Enquiry concerning Human Understanding along with various essays. While some argue that Hume’s approach to scepticism changes in these various works, especially between the Treatise and Enquiry, this essay shows how examining Hume’s discussion in his Dialogues sheds light on his overall stance toward scepticism. And this understanding of his approach in turn opens up new ways of looking at how the various characters in the Dialogues can be read as advocating or illustrating Hume’s epistemological stance. Exploring these issues will also allow us to see how Hume anticipates certain aspects of contemporary debates about reasoning about the nature of logic in general and counterpossible reasoning more specifically.