While I was growing up, conversations about homosexual relationships were a taboo subject for as long as I can remember. It is a subject that burns deep within the heart and soul of the United States. For years, some DL and Black gay men have struggled to understand the Black community’s objection to the union of homosexual relationships. The term “DL,” which is short for “on the down low,” is a common way to refer to Black men who live their everyday lives in the guise of heterosexuals, are often married to women, yet also engage in discreet relationships with other men. This first-person narrative focuses on a time when I was employed with the Centers for Disease Control and Prevention (CDC) in New York City. I reflect on some of my interactions with DL and Black gay men. I discuss how some Black men who identify as gay are oftentimes hesitant to adopt the label “queer,” and to some extent even “gay,” due to the association of these terms with whiteness. This article is Part 1 in a series of two, both published in the same issue of Visual Arts Research. It is in direct conversation with the second article, “What It Means to Be Black: DL, Black, and Black Gay Male Images in Media—A Television Criticism.” It is my intention to start this journey with “Learning to Be Black: Unreconciled Strivings of DL and Black Gay Male Identity” and end with an echoing negativity about how images of Black men are viewed and perceived in social media through a television criticism. These two articles are companion pieces, which feed off each other and rhythmically flow into a cohesive union of these most poignant and pressing topics of being DL, Black, and a gay man in the United States.