This study explored the lived experiences of Black male mentees mentored by female staff in high school school-based mentoring (SBM) programs. Specifically, it identified how their relationship achieved the four components of relational-cultural theory to improve academic achievement and support graduation. According to TEA (2022b), Black students were graduating at the lowest rate compared to the other most prevalent racial groups. Additionally, they had the highest drop-out rates compared to four other prevalent racial groups (Texas Education Agency [TEA], 2022b). This study included interviews with six former participants in the SBM program who graduated high school in the Gulf Coast region of Texas. The central question was: What are commonalities or trends in the experiences of former African American male students who participated in an SBM program with a female mentor in high school? This study revealed that Black male mentees can be authentic, experience mutual empathy and mutual empowerment, and grow-fostering relationships when the mentor fosters a positive connection that includes open dialogue and humor and builds trust. The study findings indicate that when implemented correctly, school-based mentoring can provide a safe and nurturing school environment where Black male students can reach their fullest potential. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]