The quality of the relationships that mentors forge with their proteges is assumed to significantly affect the success of mentoring interventions. Building on previous research, this study examined the association between relationship qualities and protege functioning. Multiple reporters (e.g., mentors, proteges and teachers) were used in a prospective research design spanning eight months in Israel's largest mentoring program--"Perach". The sample consisted of 84 proteges ranging in age from 8 to 13 years (M = 10.75). Qualities in the mentoring relationship such as closeness, dependency and unrealistic expectations for the continuation and deepening of the relationship, beyond the planned period, were positively associated with the children's social and academic adjustment, and contributed to perceived academic competence, social support and wellbeing. Generalization of positive mentoring experiences to other relationships (such as the mother-child relationship) and the role of unrealistic expectations and dependency as key elements are considered. Implications of the findings for research and mentoring intervention are discussed.