Two women faculty members, one White from the southeastern United States and one Black African from Zimbabwe, purposefully explored their informal mentoring relationship with the goal of illuminating the complexities associated with their cross-racial, cross-cultural experience. Concentrating on their four-year mentor-mentee academic relationship at a predominantly White institution (PWI), these women employed a dialogic duoethnographic methodology to uncover emerging, nuanced characteristics contributing to the positive nature of their mentoring experience. Calling upon a seminal nine-function mentoring framework focused on advancing mentee personal growth and professional advancement, the authors, engaged in critical interplay of dialogic considerations of their mentoring experiences, relationship, and literature. The authors revealed a distinct cross-cultural and cross-racial journey where each, as participant researcher, uncovered a deeper appreciation for the importance of engaged dialog. Emerging is a complex interplay of understandings about trust, care, and power dynamics as factors in defining mentoring relationships that work for good.