There is a great need for higher education faculty to understand the complexities of teaching students of diverse backgrounds. In this article, two Black educators mentor a White faculty member yearning to understand the nuances of the culture of historically Black colleges and universities (HBCUs) because she wants to engage her students in meaningful learning. Supported by Critical Race Theory and told through the use of counterstories, the authors identify three themes or questions from their separate narratives: race, culture, and teaching. These mentoring stories offer an in-depth view of what it means to teach from three very different perspectives--those of a White woman, a Black man, and a Black woman.