At-risk youth face many difficulties including higher dropout rates, lack of positive adult support, poor neighborhood conditions, exposure to violence, and a lack of parental support and family stability. Mentoring programs for at-risk youth may help mitigate these difficulties, but the quality of the mentor-mentee relationship is predictive of the effectiveness of the mentoring relationship. The problem addressed in the proposed study was that the perceptions of mentors and mentees regarding mentoring styles in middle schools were unknown, and without an understanding of mentoring styles the optimal procedures used in mentoring programs would remain unknown. The purpose of this qualitative study was to investigate the perceptions of mentors and mentees regarding the effectiveness of mentoring styles in a mentoring program in the Dallas Independent School District. A qualitative case study research design was used. The population of interest in this study consisted of at-risk middle school students in mentoring programs and their mentors. The unit of analysis was individual mentors and at-risk mentees at three middle schools in the Dallas, Texas, area. Six mentors and six mentees from each of the three middle schools were included for a total sample size of 18 mentors and 18 mentees and a content analysis was performed. The conclusions from this study were: (a) mentors and mentees believed that the mentoring relationship had to be genuine to be effective, (b) mentors and mentees agreed that the primary goals of mentoring should be increasing academic achievement, socialization, and personal growth, and (c) mentors believed that the best mentoring style was demonstrated by mentors who did more than was expected of them while mentees believed that the best mentoring style was demonstrated by helpful, knowledgeable, fun, and smart mentors who were good with children. It was recommended that mentoring programs should be extended to other professionals outside the educational field, and that mentees should be assigned a female and a male mentor. In the future, researchers should replicate this study in other schools and employ mixed method approaches. [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.]