Amidst trends that emphasize languishing patterns in teen mental health, there is a bright spot: social science research indicates that adolescents who develop relationships with adult mentors demonstrate increased signs of flourishing. This social science research on mentors, though limited to school performance outcome goals, offers a lifeline to character educators. I offer a theoretical framework based on Aristotelian principles, informed by anecdotal case studies of authentic moral dilemmas that emerged from the direct experiences of mentees, to suggest a framework to explain why adolescents with adult mentors have an advantage. Patterns of conversation in trusted mentoring relationships developed over time, and in a school context that provides sufficient professional development for mentors, support the youth: (1) to advance in practical wisdom ("phronesis") by honing skills for emotional regulation as well as cognitive skills to recognize goods in conflict and (2) to learn how to engage in civic friendship through these friendships of inequality with mentors.