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This essay examines the content, context and relevance of Hume's characterization of the human condition in the Enquiry Concerning Human Understanding as "whimsical." According to Hume, human beings are by nature both theoretical and practical beings and the whimsical condition is an instability generated by both theory and practice. It is the fact that by nature human beings must and do act, reason and believe with assurance and conviction, but are unable to satisfy their natural desire to justify their assurances and convictions. On Hume's account, this skepticism is cancelled neither by theoretical reflection nor human practice. Finally, Hume's text suggests that human beings suffer the "whimsical condition of mankind" not only collectively, but that it is a condition human beings experience individually, including dogmatic reasoners.