This qualitative descriptive study analyzed the role that natural mentors had in cultivating a sense of purpose and meaning among 38 diverse male and female high school students. The "types" of mentoring support provided and the students' perceived "experiences" of receiving the support were considered in the analysis. Directed content analysis revealed four initial overarching types of supportive actions that were provided by mentors: emotional, instrumental, informational, and appraisal support. The types of support offered were further categorized across three dimensions of perceived support by the mentees: (a) affirmation (e.g., the experience of emotional and appraisal support), (b) cultivation (e.g., the experience of being challenged and obtaining skills), and (c) guidance (e.g., the experience of receiving information and advice). In order for mentees to perceive and accept cultivation and guidance support, they first needed to experience an affirming relationship with their mentors. Findings may inform best practices for mentoring youth toward lives of meaning and purpose.