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Prepare2Nspire (P2N) is a near-peer mentutoring program dedicated to creating dynamic mathematical experiences for urban learners. P2N not only acts as an extracurricular outlet for in-school mathematics learning but also provides students of color social support from adult mentors. This research paper used case study methodology to examine African American male mentoring relationships at P2N. Through a mentutoring approach, African American male participants were given the opportunity to relate to mentors through shared lived experiences, essential norms were enforced within the learning community, and an emphasis was given to team collaboration. Moving forward, African American male mentorship must be promoted in order to disrupt deficit-based perspectives and increase the social and academic motivations of African American youth.