When nineteen-year-old Matthew Lewis crafted The Monk in 1796, he had no idea what hideous progeny he had created. The text plagued Lewis throughout his life to the point where he earned the nickname Monk Lewis, symbolic of criticism he and the text received equating Lewis directly with the ideas in his infamous gothic novel. The Monk rose to the pinnacle of popularity in an England consumed by its love for Gothic romances and enswathed in the language of political, social, and religious turmoil. In addition, Lewis’s novel has endured centuries of criticism to become part of the twenty-first century’s love affair with the Gothic. Elements in Lewis’s novel have spoken to humankind across the ages, primarily through his principle character, the fallen monk, Ambrosio. Why do The Monk and Ambrosio enwrap imaginations in the dichotomy between appeal and repulsion? What does Ambrosio experience in his mental and physical Lifeworlds as he catapults himself into damnation in the text, and what can humankind appropriate from his fall? This book takes a new approach to literary studies of The Monk by turning hermeneutic phenomenology in a new direction - into the minds of the characters themselves. The reader enters the mind of Ambrosio and experience the world and the symbols surrounding him, including his intersubjective constitution with other characters, as he experiences them. While applying phenomenology to a fictive text is not new, focusing hermeneutic phenomenology exclusively on the consciousness of the characters in a literary text is. The author takes this bold step thoughtfully and analytically, explaining step by step how Ambrosio takes himself down a path to damnation in his own consciousness before Satan ever throws him off of a mountain, in effect explaining how salvation for Ambrosio is impossible by the end of the novel. While previous approaches have analyzed the reader’s experience through the lens of phenomenology, this work examines a character’s experience through the lens of hermeneutic-phenomenology, analyzing symbols present in the monk’s consciousness and how they affect his mental path to damnation, as opposed to analyzing the reader’s experience through that same lens. By moving a layer deeper than traditional approaches, this work opens new realms of possibility in literary criticism.