My dissertation examines how representations of physical and mental suffering in literary texts reveal paradoxes in the structure of sympathy that remain under-explored by literary scholars. In the philosophical thought of Shaftesbury, Hutcheson, Hume, and Smith, sympathy was a feature of the "moral sense," an aesthetic intuition that, with proper training, could compel individuals to act ethically in society. However, because sympathy allowed individuals to feel the experiences of others, not just through the imagination, but in connection with the body itself, the motivation for sympathizing with pain presented a significant problem for Enlightenment philosophy. Largely divested of its religious contexts, pain was increasingly classified as a mechanism that registered distress or pathology in the body, and as an experience that human beings instinctively avoid. Terry Eagleton, Adela Pinch, and G. J. Barker-Benfield, among others, have analyzed sympathy and the culture of sentimentality in terms of their moral relativism, derivative emotionality, and regulatory influence on gendered behavior and social norms. My dissertation makes a needed contribution to the field by focusing on the ways pain reveals structural contradictions in sympathy's claim to penetrate the boundaries of subjective experience, an experience that was becoming "buffered"-- to use Charles Taylor's term -- from the influence of others. Each chapter of my dissertation positions a landmark text--Aphra Behn's Oroonoko (1688), Samuel Richardson's Clarissa (1748), Goethe's The Sorrows of Young Werther (1774), and William Wordsworth's The Prelude (1805) -- within the context of Enlightenment moral sense philosophy to highlight the intentional and unintentional ways literary authors modified philosophical formulations of sympathy to create the ethically complex pleasure of sympathizing with the pain of others. Because the concepts of pain and subjectivity were taking on modern shapes in these texts, literary critics must reconsider how ethical claims were made by the aesthetic practice of connecting representations of pain with the pleasure of sympathizing. Globalized media are bringing increasingly distant experiences of pain to our attention in increasingly intimate ways. These technologies can be invaluable for promoting a sense of social responsibility for the pain of even the most distant others, but only if we hold ourselves accountable for how and why we look.