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Increasingly, faculty and staff at Catholic colleges and universities enter into mentoring relationships with students to help them discern their callings. This essay analyzes why friendship is a helpful metaphor for understanding a mentoring relationship. Moreover, as with friendship, the author argues that good mentoring demands listening to and respecting students’ stories, but also guiding them to more hopeful narratives for life. The author also examines important ways that a mentoring relationship is different from friendship and concludes by suggesting how friendship can help mentors understand and respect boundaries in a mentoring relationship. Overall, the author maintains that if to befriend a student is to seek their good, this cannot be done wisely or well unless mentors are persons of integrity, outstanding character, and virtue.