An education professor and a high school student tell the story of their mentoring relationship, focusing on the academic journey of the protege. The narrative attempts to give voice to both mentor and protege as it relates an authentic "win-win" situation for both participants and their families. The narrative is theoretically grounded in the literature describing co-mentoring and network mentoring arrangements that are less unilateral and authoritative, and more bidirectional and relationally-based than traditional mentoring arrangements. The authors contend that since educational achievement and attainment determine to a significant degree one's participation in the "American Dream," academic assistance and guidance provide a logical area of emphasis for mentoring our youth. Important recent developments in the youth mentoring movement are also discussed.