Over the last decade, community leaders have connected with students through school-based mentoring (SBM) programs (e.g., adults who mentor at-risk students). However, research in the area of SBM is only on the cusp of understanding relationship elements for impacting youth. In this collective case study, we examined the perceptions and experiences of 11 selected mentors in dyadic relationships (i.e., mentee and mentor) to understand better ways to retain and to engage mentors for longer-lasting mentoring relationships, providing a sense of connectedness for students. Specifically, we investigated purposes and approaches of mentoring through the voices and experiences of mentors working with elementary-aged students in SBM. Results revealed self-sustaining synergy within the dyads (with little or no program support) and themes of consistency, commitment, spirituality, playfulness, the use of self-disclosure, creativity, and emphasis on the present. In addition, implications for cross-cultural and, in particular, cross-age mentoring are discussed. One exemplar case illustrates specific profile characteristics used to bridge age, gender, and cultural differences.