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While research indicates that school-based mentoring programs for at-risk students help to increase their self-esteem, academic growth, and positive schooling experiences, there is limited research that examines the benefits associated with those experiences for the mentor. Therefore, the purpose of our study was to examine pre-service teachers’ perspectives about their gains through mentoring at risk-youth. Qualitative reduction strategies generated three dominant themes: (a) building rapport, (b) authentic praxis, and (c) dispositions. Our findings suggest that pre-service teachers benefit pedagogically and socially from mentoring at risk youth. Our findings also inform school administrators, field-based faculty, and other individuals who have direct influence on mentoring initiatives, about the value of providing pre-service teachers with opportunities to interact with at-risk youth.