Numerous studies have examined mentoring relationships and their consequences for youth development (Rhodes and DuBois, 2008). DuBois and Silverthorn (2005) found that those who reported having had a mentoring relationship during adolescence exhibited significantly better outcomes within the domains of education and work (high-school completion, employment), mental health (self-esteem), problem behavior (gang membership, risk taking), and health (exercise, birth control use) (Rhodes and DuBois, 2008). Currently, there is limited research available that focus on mentoring programs and the characteristics that influence the relationship between the mentor and mentee. Also, research focusing on mentoring programs of African American fraternities does not exist. This exploratory case study was designed to examine the role and impact of an African American fraternal organization's mentoring program on the success of its mentees. Data collection for this study included observational notes from thirteen mentoring session activities, four mentee interviews; two mentees new to the mentoring program and two mentees who have participated for at least one year, and one mentor focus group consisting of ten mentors. The Mentee Attitude Scale was also administered to thirteen mentees. The data were analyzed to identify the six themes that impact the mentees' successes based on the Relational Theories methodological approach. The most prominent themes to appear across all data points were: Interactions, collaboration, brotherhood, trust, mentor preparation, and education. To investigate how the themes related to how impactful participation in the mentoring program was on the mentees' success, Relational Theories' components authenticity, empathy, collaboration, and companionship were used. Each component has a direct correlation with the recurring themes. Based on the results of the study, mentees' success is positively impacted by how enjoyable the experiences are during the mentoring sessions. To reach a high level of enjoyment, mentees must be able to feel as though they can trust the mentors. The mentees must also believe that the mentors understand situations that are currently impacting their lives. The mentees must have a voice in what occurs during mentoring sessions as well. Finally, mentors and mentees must enjoy spending time together and enjoy each other's company. [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.]