To optimize the effectiveness of youth mentoring it is important to begin to identify specific preexisting characteristics of mentors that lead to positive experiences for adolescent mentees. College women mentors, aged 18 to 22 years, were paired with middle school girls, aged 11 to 14 years, for weekly one-on-one and group mentoring in an 8-month, school-based youth mentoring program. For the sampled 142 mentor-mentee dyads participating in the program, mentor's reported academic self-worth, parent relationship, and not being too autonomous were important preexisting characteristics related to mentee satisfaction. Mentor's initial level of depression was negatively correlated with mentee's self-reported improvement in competence, while mentor anxiety was positively correlated. Finally, the relationship between mentor's autonomy (negative) and ethnocultural empathy (positive) and mentee outcomes were stronger for cross-race versus same-race pairs. Implications for mentoring programs that use college students as youth mentors are discussed. (Contains 4 tables.)