The purpose of this dissertation is to investigate how three school-based mentoring programs are preparing African American male youth for post- graduation, college, and careers. The influence of mentoring experiences and mentoring relationships are addressed in order to uncover the influence of racial matching on the mentoring relationship. Mentee and mentor interviews were compared to evaluate the personal perspectives past participation in Chi Omega Lambda, Kappa Leadership, and Theta Phi Psi mentoring advocate program and the mentoring experience. Mentees and mentors expressed overall satisfaction with the mentoring experience and positive comments on the mentoring relationship. The interviews did not reveal differences in the mentoring experience based upon the race of the mentor, but the opportunity for preparing mentees for college and college access differed more for one of the organizations verses the other two. [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.]