Black males have lower college completion rates than Black women and all other racial and ethnic groups in the United States. The majority do not finish college. Although HBCUs are known for being a supportive environment for Black students, they too struggle with graduating Black males. One of the barriers to Black males’ success at HBCUs is poor help-seeking. The purpose of this study was to gain an understanding of the help-seeking experiences of Black male students in order to construct methods of helping them to build healthy attitudes toward help-seeking. In-depth interviews were used to investigate the help-seeking experiences of first year/first generation Black males at a southeastern HBCU prior to them coming to college. Five students with positive associations with help-seeking and four students with negative associations from various family backgrounds were interviewed. Once the data was transcribed, coded, and analyzed, three key findings were yielded. First, participants were taught to be self-reliant and were taught masculine ideals incongruent with help-seeking (7/9 participants). Second, every participant faced negative evaluation by their peers, which made them reluctant to seek help. Third, participants perceived help-seeking as an experience in conflict with their pride (7/9 participants) and became altruistic, preferring to help others than to seek help themselves (6/9 participants). Implications of this study called for the redirection of Black males’ altruism toward interests and career paths that can increase their engagement and highlighted the importance of intervention programs both in college and before college in order to promote healthy help-seeking behaviors by Black males. This study contributes to a growing body of research on improving the retention and academic progress of Black males at HBCUs.