This chapter reports on research findings in relation to youth perspectives on the quality and characteristics of mentors and the mentoring relationship. The helpful characteristics and relational qualities of mentors identified by youth reflect the findings of previous research, including being relaxed, having shared interests and compatible personalities and being non-judgemental. The importance of empathy, honesty, continuity and help with decision making also emerged from the findings. The voluntary nature of the BBBS programme and the fact that mentors often had relevant experience of youth work or social care were identified as important. This chapter also reports on how young people differentiate the mentor from other family and peer relationships. The findings indicate that the majority of young people see their relationship with their mentors as having the characteristics of a naturally formed friendship, whereas relationships with social workers are viewed more as a professional-client relationship. In the discussion, the findings are discussed with reference back to the literature and research and with a specific focus on relational cultural theory.