<p>It is difficult to understand distant places and peoples, but easy to believe we understand them. We are limited by many factors including our geographical imaginaries and preconceptions. When we refuse to admit that we do not understand or insist that we understand others fully, we misunderstand them. People and places are complex and misunderstanding them can be worse than knowing little about them in the first place. This article explores geographical imaginaries and their roll in misunderstanding distant places and peoples. My guide for this endeavor is G.K. Chesterton, the English journalist, novelist, and social critic, who had a sense for how psychological and sociological factors, and uneven power relations influenced geographical imaginaries. Chesterton was particularly critical of imperialism and imperial imaginaries and believed they were epistemically harmful. He believed it perilous for imperialists to believe they understood the peoples and places they subjugated. He approached misunderstanding within a variety of contexts criticizing ageographical representations in newspapers, certainty about our knowledge, and the near impossibility of understanding others when those relationships are based on uneven power relations. He grasped that our attitudes influence us to believe what we want to believe about others. Chesterton explored what could appropriately be called <i>geographies of misunderstanding</i>, illustrating that geographical literacy goes well beyond just knowing things about places. It also entails the recognition that we do not understand places. Indeed, we cannot understand others until we admit we do not understand them.</p>