As a practitioner who has scored many admission essays, the author has noticed that numerous colleges and universities include questions that seek to expose and evaluate students' interactions with diversity, equity, and inclusion. Frequently, applicants are encouraged to disclose a difficult moment in their life and share how they overcame it. The approach to college admission undoubtably affects a wide array of students. This article is focused solely on how those practices impact Black men. The way the author approaches this issue is framed by his positionality; the support he provides to Black men; and the ways he works to push back against the deficit model used most frequently to examine the recruitment, retention, and matriculation of Black males in higher education. With that in mind, take a step back and consider the ways these questions work to uphold and support existing structures of inequity while also erasing the unique identities of applicants, particularly Black males.