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Mentors for adolescents are widely believed to improve life chances and reduce problem behavior. Using 42 retrospective qualitative interviews with undergraduate former high school athletes and social learning theory as a framework, we investigate what it means to adolescents to matter to their school‐based natural mentors. Findings indicate that natural mentors represent a fundamental social connection that helped participants feel like they mattered. We identify three structural domains of social identity in which mattering operates: relationship, gender, and athletic. Natural mentoring led to connecting with non‐kin, feeling important, and creating accountability to significant others. Mentorship and mattering were deeply gendered; in reinforcing attributes of athletic success and physical or mental growth, mentor relationships both contributed to and helped subvert the structure of traditional gender roles and provide insight into the ways men and women navigate the contested and gendered space of sport. Finally, these mentoring relationships demonstrated the intersectional nature of sport and its physicality by linking the body and soul. Mattering is the mechanism for social learning that facilitates these crucial relationships. The implications of these findings are discussed, along with suggestions for future research. [ABSTRACT FROM AUTHOR]