While mentoring programs are prevalent, limited research focused on the mentors' experiences exist, particularly during critical periods of development. Using a qualitative, grounded theory approach, this study explores the elements of the mentoring experience for a cohort of late adolescent/emerging adult women in a long-term program. Outcomes described were both personal and work related, as well as relationally and individually focused. In addition, a number of individual, relational, and programmatic challenges, along with associated emotional challenges, were reported. The influence of these challenges on outcomes, however, depend on a number of elements that appear to buffer the negative experiences. The organization of the findings into a conceptual model informs both research and practice.