Theoretical and empirical work on youth mentoring relationships has been largely focused on the mentor-youth dyad, with little attention to the larger context within which such relationships form and develop. The perspectives of parents have been absent for the most part from the mentoring literature to date. In-depth, semistructured, qualitative interviews were conducted with parents (n = 13) of youth who were participating in a community-based mentoring program. Four major themes were identified: parents' (a) hopes and expectations for the mentoring relationship, (b) trust in the mentor and satisfaction with the relationship, (c) roles in the mentoring relationship, and (d) reflections on and experiences with cultural differences between their child and the mentor.