In this study, we investigate the role of matching communication (i.e., relational messages received) in mentoring outcomes (mentor and protégé career attitudes). Specifically, we used data from a sample of 145 matched mentor–protégé dyads in a response surface analysis to show that matched relational messaging generally relates to mentors (and less consistently, protégés) reporting enhanced career satisfaction and career commitment. Furthermore, our findings are consistent with previous research showing that when relational messages (i.e., intimacy) or self-disclosure are matched at high or low (i.e., more extreme) levels, the mentor and protégé have the best outcomes. Additionally, beneficial mentor outcomes were maximized when levels of seriousness were matched at a moderate level. These results suggest that both levels of relational messaging, as well as the degree to which mentors and protégé match on these constructs influences mentoring outcomes. Study limitations, future directions for research, and implications for career development are discussed.