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This article examines Augustine’s early dialogues from the perspective of the feeling of shame. First, Augustine’s early negative conception of shame as a hindrance to an unconditional search for truth is determined and considered in connection with the broader Augustinian theory of shame, which was more elaborately formulated and more theologically motivated in Augustine’s later works, such as De ciuitate Dei. Second, Augustine’s dialogues are considered from this point of view as works that are intended to encourage their readers to overcome the negative effects of shame and to search for truth wholeheartedly, even if it would require admitting one’s own errors and receiving correction from one’s dialogue partners. As a result, the present study aims to shed new light on Augustine’s early conception of shame and on the style and purpose of his early philosophical dialogues.