The purpose of this study was to explore the mentoring process, specifically the interactions between mentor and mentee in the context of an adolescent mentor program. Adolescent programs, conducted at several high schools, were included in the study. The findings indicated that what occurs during the process of mentoring is multi factorial, complex and diverse. Mentoring takes place in a reciprocal way that is impacted by layered contexts. Implications for professionals wishing to work as mentors or wishing to implement mentoring programs are examined in this study. These include the need to recognize and comprehend mentor qualities and styles vis a vis various theoretical constructs such as role modelling, identification and inter subjectivity. Little research has been identified that brings the narratives of both mentor and mentee together in one study comparatively analysing them. In this regard the present study can be seen as unique and contributing something new to the literature on mentoring.