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Black males living in single parent homes shared that, in spite of never having a mentor, they understand how mentoring can enrich their lives and the importance of same sex, responsible mentoring. Participants shared specific, will-expressed thoughts on what they believed the ideal mentoring relationship should involve. In their opinions, effective mentoring offer leadership in both social and academic development and includes their mothers in the process, which are components of Strategic Mentoring. They characterized Unstructured Mentoring as an unclear, jumbled process with no set agenda, while they described Strategic Mentoring as mentoring with a clear objective. Effective mentoring should be a strategic, organized process that adds value and purpose to the life of the mentee.