In October 2013, the Pacific Institute for Research and Evaluation evaluated the Big Brothers Big Sisters of Kentuckiana (BBBS-Ky) mentoring program. The three parent/guardian factors examined were parent-child dynamics, family dynamics, and parent/guardian involvement in the mentoring. The evaluation found that parental-youth relationship dynamics and parenting styles had a direct impact on youth attitudes toward risk behaviors. For youth in site-based matches, these parental-youth factors were related to academic performance, unexcused school absences, and school suspensions. The evaluation also found that although parent/guardian involvement in mentoring relationships influenced ratings on the strength of the relationship, apparently it did not directly influence program outcomes for the youth. On the other hand, relationships between parents/guardians and mentoring volunteers influenced both the strength of mentoring relationships and two key youth outcomes, i.e., attitudes toward risky behaviors and academic performance. The evaluation used an intervention-only pre-post design in which the BBBS-KY program at the beginning of the mentoring and 12 months after the mentoring began. These data were complemented by school record data from 16 area school districts and data from the BBBS-KY database. Recommendations are to tailor parental engagement efforts to program design; to support the development of strong, positive relationships between parents/guardians and volunteer mentors; prioritize parental engagement in site-based matches; and gain a better understanding and alignment of mentoring expectations among parents/guardians, volunteer mentors, and agency staff.