In this study, we investigate the role of matching communication (i.e., relational messages received) in mentoring outcomes (mentor and prot & eacute;g & eacute; career attitudes). Specifically, we used data from a sample of 145 matched mentor-prot & eacute;g & eacute; dyads in a response surface analysis to show that matched relational messaging generally relates to mentors (and less consistently, prot & eacute;g & eacute;s) 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 prot & eacute;g & eacute; 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 prot & eacute;g & eacute; match on these constructs influences mentoring outcomes. Study limitations, future directions for research, and implications for career development are discussed.