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First year medical students (MS1s) increase their skills in medical professionalism and their understanding of adolescent needs and cultural humility through an intermediate and high school health career pathway/mentoring program. Teaching and service-learning activities incorporate health promotion and traditional Native Hawaiian practices and provide experiences that help MS1s to understand concepts important to medical professional development and adolescent mentoring. The content of this article was presented as a workforce development session at the 2018 Pacific Region Indigenous Doctors Conference. Methods: This article describes the program curriculum for MS1 community health electives mentoring rural, underserved, predominantly Native Hawaiian students and examines the training elements and reflections from 40 MS1s participants in the first four years of the Nānākuli Pathways to Health teen mentoring program. Student reflections were themed and analyzed for content discussing the students' professional development and experience in mentoring. Results: Analysis of four separate medical student cohorts enrolled in a teen mentoring community health elective demonstrate that mentoring relationships and program curricula helped them to develop skills in medical professionalism including establishing relationships, self-reflection, self-evaluation, communication, compassion, excellence in teaching, and a deepened understanding of native Hawaiian culture and health disparity.