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What is wonder? What would it mean to live our lives in wonder or with wonder? Is it possible for wonder to play an integral role in our aesthetic, ethical, and pedagogical experiences? Philosophy is said to begin with wonder. For Plato, wonder is the arche that grounds all philosophical inquiry. I propose to begin my ethical and aesthetic investigation of wonder with Plato, but, unlike Plato who places the imagination’s capacity to be astonished at the bottom of a hierarchy that quests for knowledge and understanding, I will argue that an ethics and aesthetics based on wonder would allow for the imagination to play an active role in all our encounters. First, I look at different philosophical treatments of wonder and then consider the role wonder plays as a virtue. Next I examine the wondrous in relation to aesthetic and ethical experiences, exploring art exhibits and a play, and conclude by drawing upon the many sides of wonder and considering its role in education. In my wanderings on wonder, I seek to value wonder as an integral part of ourselves, in all our imaginings, understandings, growth, and knowledge acquisition.