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There are many efforts to defend the Humanities against countless attacks by university administrators, the public, and, implicitly, even by students. In light of those problems, this article returns to three of the most important intellectuals in the history of western culture, St. Augustine, Boethius, and Francesco Petrarch, examining their respective fundamental dialogic narratives in which they probed their own self and discovered answers to the most critical questions in life. This paper suggests that we can profoundly promote the Humanities by returning to the bedrock of our discipline established by these three authors whose concepts about the self and its relationship with the transcendental being (the divine, Summum bonum, etc.) continue to offer central perspective also for the twenty-first century.