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This research presents findings of an inquiry investigating the nature of a mentoring relationship between a White female mentor and a Black male mentee from different generations. Issues of cross race, gender, and age in mentoring relationships are largely under-researched and there is a need to understand the interactions and issues involved..The study used Author Cross Cultural Analysis Process to examine the cultural barriers, facilitating factors and outcomes of the relationship. It builds on the research conducted in the field dealing with the impact of cultural differences upon mentoring; proposes criteria on how to create mentoring relationships to foster growth in future leaders in higher education; and initiates a conversation about how cultural differences can be used as strengths.