This thesis will discuss how Maggie Tulliver in George Eliot’s The Mill on the Floss and Isabel Archer in Henry James’s The Portrait of a Lady are closely influenced by a sympathetic understanding of the eighteenth century philosophers. Adapting a Smithian sympathetic perspective in reading those two Victorian novels, I will identify sympathy as an intentional and ethical cognitive exercise, where imagination is necessary and is associated with aesthetic experiences. By tracing back to the eighteenth century sentimentalism and Romanticism, I will argue that moving from Maggie's self-renouncing absorption, Isabel achieves a Smithian sympathy as James's narrator allows her future to be unknown in ambivalence. Inheriting the values of morality in sentimentalism, Romantic literature shows a more pessimistic attitude that is manifested in the Romantic spirit’s sense of loss. I will indicate how this sense of loss is presented in the romantic tendencies in Maggie and Isabel, who are both depicted as sentimental and imaginative women, though their destinies work out differently. Interpreting the lives of those protagonists as two case studies, I will point out how a sympathetic-thinking determines Maggie’s failures and Isabel’s successes in reconciling with herself and in relations to others through rethinking her past and imagining her future. Whereas Eliot’s narration in The Mill is closer to the conventional sympathetic type, James further breaks through the convention with a Smithian abstraction.