Evidence suggests that African American male students from single mother households may face more challenges than white male students in obtaining educational success in terms of graduation and test performance. This association has been generated from previous studies that identified themes of poverty, parents' lack of education, absent parents, and poorer school systems. Yet questions remain for why educational challenges persist for African American males from single mothers who are middle income and college educated. Through lenses of social cognitive and student engagement theories and a grounded theory research approach, data were collected via semi-structured interviews with 5 mothers to explore their perceptions of their sons' levels of interest in education and mentoring to increase their sons' educational interests. A grounded theory emerged from the data, where the mothers expressed the criticality of informal, same gender, mentor relationships to improve their sons' educational outcomes. Such relationships are important because mothers' influence can be muted by peer influences as sons seek to fit in socially. Given the reported lacks of consistent male role model input and appropriate mentor programs for middle-class African American male students, the value and impact of the informal mentor is critical. The results of this study highlight the importance of same gender relationships over same race relationships to teach adolescents how to be responsible men and contribute to society. The findings of this study provide educational leadership with a deeper understanding of the needs of these students, through the viewpoint of their mothers, which may contribute to positive outcomes among adolescent Black male students, a group that continues to struggle with poor academic and social outcomes. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]