Previous research in this area has focused primarily on parent/guardian roles in mentoring relationships, mechanisms by which parent/guardian involvement can support or hinder the development of strong mentor–mentee relationships, and motivations for parents/guardian involvement in mentoring relationships. This study goes beyond previous work by providing quantitative evidence from two types of mentoring programs that parent/guardian, volunteer, and youth satisfaction with mentoring relationships impact both match strength and match length. In keeping with previous research, volunteer reports of match satisfaction (quality time) ratings were the strongest predictor of volunteer SOR ratings and youth reports of satisfaction (quality time) were the strongest predictor of youth SOR ratings. As noted above, we found that parent/guardian satisfaction (goals) with the match influences both youth and volunteer match strength ratings and that parental satisfaction (goals) with the match was the only predictor that was significantly related to match length. Taken together, these findings indicate that parental satisfaction with the match has a strong influence on match strength and length. These findings are important both for the research community and for mentoring programs.