This study compared perceptions of mentoring relationships among early adolescents, middle adolescents, and emerging adults. In ten focus groups, 56 middle school, high school, and college students described relational experiences that were analyzed thematically. Differences in the characteristics of the mentors nominated by the youth across the age groups were noted and five broad themes identified. Three themes were similar across the different age groups: (a) the importance of spending time together and engaging in shared activities, (b) trust and fidelity, and (c) role modeling and identification. Two themes were present in the narratives of all three age groups but played out differently in ways that were consistent with developmental issues and needs of that age group: (a) balancing connection and autonomy and (b) empowerment. These data can help guide future research and practice involving youth mentoring relationships across developmental and disciplinary divides.