Results provided evidence that deep and lasting relationships could be formed through formal mentoring programs. However, the complex and bidirectional nature of the relationship between adolescents and their adult mentors was also highlighted. The success of the relationship depended on the joint commitment and emotional involvement of both parties, although it was noted that the adult had to “carry the load” of the relationship during the beginning as the adolescent slowly gained trust in the adult. Through time the adolescents became increasingly authentic and engaged in the relationship. The ability of the mentor to develop and sustain empathetic feelings toward their protégée was also a central feature of successful mentoring relationships. The author suggests that mentoring programs should offer training on cultural awareness, particularly in cases where the social distance between the mentor and protégée is great. Participants were 24 pairs of adults and adolescents involved in mentoring relationships that ranged in length from 1 to 4 years who were recruited from the Big Brothers and Big Sisters Associations located in an urban community. The sample was purposeful as the author was exploring the nature of successful mentoring relationships. Participants completed semi-structured interviews in pairs as part of their planned mentoring activities for that day. Interviews focused on expectations going into the relationship, memories of their first meeting, typical activities, special or memorable times, times of conflict, anticipated length of the relationship, and the types of support the relationship had provided to the adolescent. Following the interview process, eight interviews were selected with which to conduct an interpretive analysis using the listening guide method. All 24 interviews were then analyzed for the following themes: authenticity, empathy, collaboration, and companionship. Given the popularity of mentoring programs around the country, more evaluative research on these programs is needed. Tables, note, references