The fragility of youth-adult mentoring relationships requires innovative program components to support and sustain these relationships and enhance participant outcomes. The current study presents and explores the experience of a unique mentoring program component known as Mentor Families, in which three to four pairs of mentors and mentees engage in structured activities together. Grounded theory methods were utilized to explore the experiences of mentors (n = 212) and mentees (n = 87) involved in Mentor Families within a mentoring program for adolescents at risk for delinquency. Findings from the current study reveal that Mentor Families provides a place (a) for mentors to receive support and supervision, (b) for mentors and mentees to belong, and (c) for mentees to grow and learn. These findings suggest that Mentor Families warrants further investigation as to how they may positively affect mentoring relationships and programs.