School engagement is an important predictor of graduation. One strategy to enhance student engagement is mentoring. Check & Connect is a structured mentoring program that has resulted in favorable outcomes for many students, including those with emotional and behavioral disorders. Effectiveness, however, depends on the quality of the mentor-mentee relationship. Although research has examined factors that increase relationship effectiveness, findings have been inconsistent. We explored the perceptions and correspondence of 166 high school students (i.e., mentees) with social, emotional, and/or behavioral challenges and their mentors about the mentoring relationship and variables that contribute to relationship quality. Results indicated that mentors and mentees rated the relationship favorably and their ratings correlated moderately. Mentor and mentee variables examined (gender, ethnicity/race, age) were not significant predictors of relationship quality; however, specific topics discussed during mentoring sessions for mentors (family, friends) and mentees (school, future plans) were significantly related to their perceptions of relationship quality.