This dissertation follows the development of the mentor figure from Frances Burney’s Evelina published in 1778 to Maria Edgeworth’s Belinda in 1801. The mentor becomes a key figure for exploring women’s revolutionary ideas on female education and women’s roles in society. My dissertation contributes to discussions on mentoring, development of the Gothic mode, and debates over sensibility and sentimental fiction. It considers how the female mentee paradoxically both desires and criticizes her male mentor and his authority. Each author under discussion employed the mentor figure in a way that addressed their contemporary society’s issues and prejudices toward the treatment of women and the power of sensibility. Much of this treatment was traced to a conversation of reforming female education from an accomplishment-based pedagogy to a moral, intellectual-based instruction that was more masculine in nature (emphasizing a balance between sensibility and reason). Frequently, the mentor provides general comments and recommendations about love to his female pupil, who is entering into the marriage market, but his advice often turns out to be wrong or misplaced since it does not fit the actual situation. He is a good spiritual guide but a poor romantic advisor. I assert that the mentor figure’s usual lack of romantic sentiment and his pupil’s ability to surpass him in matters of the heart reveal a tendency to subvert male authority. Throughout this discussion, questions related to gender arise. Women’s desire for their own agency and control over both their minds and bodies underpin much of women’s eighteenth-century fiction. My dissertation explores these complex relationships between male mentors and their female pupils.