There is constant debate over the contributing factors that produce disproportionate outcomes in higher education between Black and White students. This study utilizes a symbolic interactionist theoretical framework and a qualitative phenomenological approach that pulls from the individualized and collective experiences of faculty, administrators, and Black students at historically Black colleges and universities (HBCUs) and historically White colleges and universities (HWCUs), and examines their cultural and social experiences. Findings from this study highlight the cultural mistrust (CM) of Black students for White faculty at HWCUs, which complicates relationship-building processes. It also highlights Black students' heavy reliance on communication for relationship-building with faculty/administration, which leads to them being more "culturally trusting" and maintaining a more rigorous, judgmental process of determining whether to continue to trust and create relationships with faculty. Although cultural familiarity and cultural environments lessened the CM of Black students at HBCUs, it was still a significant factor pertaining to White professors' perceptions of Black students. Data from this study can possibly enable faculty/administration and policy-makers to develop and implement strategies for increasing positive experiences for Black students that lessen retention, increase matriculation and graduation rates, self-esteem and lead to better career opportunities.