This article focuses on the experiences of four faculty members engaged in cross-racial mentoring at predominantly White institutions in the United States. Using scholarly personal narratives, the study addresses psychosocial and cultural struggles that both White and Black faculty members experience as they mentor individuals of differing ethnicities. The participants were a Black woman, a White woman, a Black man, and a White man, all of whom were faculty members. Their narratives shed light on difficulties precipitated through cross-racial interactions regardless of social station, racial identity, or racial awareness. The study provides a unique, emic perspective that addresses ideas of ambivalence, White privilege, Black social reticence, and White obliviousness as well as summarily advancing the discussion on faculty-student engagement in cross-racial mentoring. Ultimately the authors challenge themselves and faculty colleagues to be uncomfortable as they learn more about social stigmas, racialized stereotypes, cultural misconceptions, personal gaps in social knowledge, internal frustration, and social inequality.