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Bronfenbrenner’s Ecological Systems Theory posits that an individual’s microsphere relationships significantly affect their development. This mixed-methods case study examined mentee perceptions of their mentoring relationships, sense of belonging, and general well-being from high school students to alumni in their 80s, occurring in their microspheres. Quantitative data were collected from student and alumni mentees using a combined survey (MYAS, SBS, 14-SGWB). Mentees generally had positive perceptions of their mentoring relationships and more neutral feelings about belonging and well-being. Mentees with positive perceptions generally showed higher levels of belonging and well-being. Qualitative data from structured interviews provided insight into the complexity of the relationships. This case study could be applied in other organizational contexts to examine mentee perceptions of informal mentoring.