This book explores the eighteenth-century concept of "mentorship" in literary works, founded on voluntary, reciprocal engagement that nurtures mutual respect, esteem, and affection. It argues that mentorship involves not just a meeting of minds but facilitates a psychological, spiritual, and emotional expansion that is essential for both participants' self-actualization. The book draws upon depictions of mentorship in eighteenth-century literature, which accounts of mentoring relationships between authors and of reader's mentorship by these texts. It argues that these testify to an experience of self-development which anticipates therapeutic relationships and offers insight into the psychological dynamics at play. Although the argument is informed by concepts developed by the psychotherapeutic tradition, it makes those insights accessible to those who have not read this theoretical material, making the book accessible for readers of fiction, at a layperson, undergraduate, and postgraduate research level. Through psychotherapeutic and psychoanalytic lenses, the book examines how literary mentoring in eighteenth-century relationships reflects and influences the development of self, illuminating the period's pedagogical preoccupations and the enduring impact of mentorship on individual and cultural transformation.