Core and capital mentoring relationships have been demonstrated to be distinct types of relationships that have different characteristics, qualities of the relationship, and are linked to different outcomes among adolescents more generally. The present study adds to this growing literature base by examining whether this typology captures well the experiences of systems-involved youth. A thematic analysis of interviews with systems-involved young people about their youth-initiated mentoring relationship indicated that capital mentoring relationships had an explicit future-oriented nature about them, with a central focus on educational and vocational goals. These mentors also provided financial literacy and life skill training. Young people in core mentoring relationships spoke of their time together quite differently, instead, focusing on provision of emotional support, specifically reassurance and positive appraisal, coupled with a kin-like description of the mentor (e.g., "like a family member"). This study adds nuance to our growing understanding of the distinctions between core and capital relationships and the findings here also indicate that some mentoring relationships were sometimes a true mix of core and capital mentoring. Also apparent from this analysis was the central role that the provision of experiential empathy played in both types of relationships.