Formalized mentoring programs have found a place as both a preventative measure and as a direct intervention in the lives of youth. Previous literature and studies of mentoring programs show mixed support for positive outcomes for participants. Literature also suggests that positive outcomes are most likely to occur in relationships that foster emotional connectedness between the mentor and mentee. However, very little research has been done to examine the course and development of closeness and satisfaction in the mentoring relationship. The aim of the current project was to evaluate mentee outcomes in the One-to-One Mentoring Initiative as well as explore the development of emotional connectedness in the mentoring relationship. Data from the first three years of the mentoring program, involving 68 youth ranging from fourth grade to eighth grade, was used to examine outcomes in GPA, unexcused absences, behavioral referrals, and teacher ratings of classroom performance. Additionally, data from bi-weekly ratings of closeness and satisfaction were used to examine the patterns of emotional connectedness. While results of this evaluation tended to show unexpected mentee outcomes in measures of school performance, several factors outside of the mentoring relationship may have also had an impact, including low number of participants, difficulty in measures, and contextual factors regarding the closing of the school. Regression analyses suggested that longer duration of the relationships contributed significantly to lower numbers of unexcused absences. Mentor ratings of emotional connectedness increased when mentors and mentees met frequently during the school year. Additionally, this study offered a unique look at the patterns and course of development for closeness and satisfaction which varied considerably across matches. Implications for program development and future research are discussed. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]