The goal of this thesis was to learn about the relational processes that underlie mentoring relationships between at-risk youth and their adult mentors. An exploratory, qualitative study was undertaken to determine how mentors and mentees experienced mentoring and how they defined their relationship. In-depth interviews were conducted with 10 mentoring pairs (10 youth mentees and their adult mentors) taking part in a community-based mentoring program. Interviews were analyzed to identify both the relational processes that characterize this relationship and the complexities that accompany the processes of managing intergenerational relationships. The study's findings indicated that the three main relational processes that characterize this relationship are: shifting expectations, defining the relationship, and negotiating the relationship within a larger social context. The study revealed that mentor relationships are tricky to negotiate because these relationships are influenced not only by the partners but by the familial network of the mentees. Additionally, partners often struggled to define the relationship because the intergenerational nature of the friendship meant that they were friends but not equals. The study provides insight into how communication within mentoring relationships helps partners negotiate their roles and definition of the partnership.