St. Jerome’s letters are our main source of evidence for how he practiced spiritual mentoring. The interpersonal dynamics between mentor and disciple were important, even essential, to fostering spiritual growth. Jerome commented a number of times about the limitations of the written word as opposed to the human voice. How could one overcome the obstacles of distance and the shortcomings of written communication to foster a sense of personal connection with one’s spiritual disciples? Jerome’s letters show that persons separated by long distances might still come to have strong emotional ties. This paper will focus on Jerome’s letter exchange with the young cleric Nepotian, nephew of Jerome’s friend Heliodorus, as an example of a relationship fostered by such techniques. Using ancient epistolary theory as well as insights from Sarah McNamer’s work on medieval affective meditation, and Carol Harrison’s book,The Art of Listening, this paper will show how both Jerome’s techniques of letter composition and Nepotian’s techniques of reading served to create, or at least to encourage, the development of love and affection between mentor and disciple. These methods fostered a dynamic of reciprocity between mentor and disciple, as both sought to grow in the love of God and neighbor.