In this chapter, we draw on experiences as an intercultural married mentoring team (Chang and Luke) and those of two of our recent mentees (Hassy and Erin) to examine an approach to mentoring grounded in self-determination theory and social learning theory. We, Chang and Luke, reflect on our own lives and academic mentors from various backgrounds, and how those experiences have scaffolded the development of our own mentoring styles and philosophies. We explore, in particular, how we approach mentoring at an institution and department in which most of our students do not share similar demographic backgrounds and experiences with either of us. Reflections from Hassy and Erin are then used to illustrate mentee’s experiences and perspectives on these dynamics. The chapter joins the mounting evidence from recent empirical efforts to debunk the mentor–mentee matching myth, and instead highlights the importance of cultural awareness, efforts to address race and gender-related barriers, and collaborative training as key skills for fostering students’ success and well-being.