Juvenile mentoring programs are an institution of informal social control that through programmatic design intends to mitigate delinquent behaviors with the development of strong quality social bonds. In these programs, mentees involved in the juvenile justice system are matched with older mentors to form social bonds as a method of encouraging prosocial behaviors. The Juvenile Reentry Mentoring Project (JRMP) is one such mentoring program matching juvenile mentees in the justice system with undergraduate mentors. Research is clear that the longer the match relationship, the stronger the relationship (Rhodes, 2007; Garringer et al., 2017). Yet, research is limited as to the program and relationship factors contributing to lasting quality relationships specific to juvenile reentry mentees (Bazron et al., 2017; Tolan et al., 2014; DuBois et al., 2006; Abrams et al., 2014). Elements understudied include the mentor’s approach to the match, mentor and mentee characteristics, and the dosage needed to produce a longlasting quality relationship. This study attempted to better understand whether these factors contributed to the quality and length of a match relationship for matches in the JRMP. I used an exploratory sequential mixed methods research design to evaluate the potential contributing factors. Given the limitations of the study, particularly relevant the sample size for analysis, findings identified various factors potentially contributing to the quality and length of a match relationship. The results provide insight and direction for improved data collection and future research