In October 2013, the Pacific Institute for Research and Evaluation (PIRE), in partnership with Big Brothers Big Sisters of Kentuckiana (BBBS-KY), was funded by the Office of Juvenile Justice and Delinquency Prevention (OJJDP) to implement a mentoring research best practices project that explored whether three types of parent/guardian level variables (psychosocial parent/family characteristics, parent engagement in the mentoring match, and parenting style) influence match quality, match length, and youth outcomes. This study was designed to describe these factors, as well as investigate how these factors impact match length, match strength, and youth program outcomes. Data to inform both objectives was collected using a longitudinal multimode approach with youth, mentors and parents in the BBBS-KY program in the metro Louisville area. In addition, data from 16 local school districts provided measures of academic performance, school attendance, and disciplinary suspensions. Data were collected at multiple time points from youth, volunteer mentors, and parents/guardians. These data included BBBS-America standard surveys (Youth Outcomes Survey, and Volunteer and Youth Strength of Relationship Surveys). PIRE supplemented the standard BBBS data collection efforts with project-specific baseline volunteer mentor survey and several formative and outcome based inserts to supplement the data that was regularly collected from youth and mentors. The PIRE and BBBS-KY teams also created a project-specific parent/guardian survey to better understand the impact of parental factors on match dynamics and youth mentoring program outcomes. Due to low literacy levels of parents/guardians, this survey was administered as a mixed-mode, audio-computer assisted interview (ACASI). Additional data sources for this study included data from (a) coding of qualitative case review notes for selected aspects of matches by BBBS-KY match support specialists, (b) academic data collected from school districts, and (c) data collected on general match characteristics (e.g., match closure status) collected by BBBS-KY as part of their standard business operations. Most measures were collected early in the match (either match formation or three months into the match) and at 12 months into the match.