Vacant esteem, according to Post Traumatic Slavery Syndrome’s (PTSS) theory, asserts that one has little or no self-worth because of inferiority from social, communal, and familial spaces (McDougal,2014 & DeGruy, 2017). Within PTSS, perceived inferiority is a direct result of African Americans adapting to racism and oppression. My research focuses on self-esteem development among African Americans over age of 18 with a sub-interest that connects African American socialization, social discourse, and the normalization of a cultural communication game, aka, “playing the dozens.” This study highlights PTSS’s “vacant esteem” tenet, its permanence in the Black community, and its connection, if any, to self-esteem development. Via interviews, I focalize the trajectory of perceived self-esteem for participants from youth into adulthood - resulting in a socially investigative influenced mini documentary. This study provides additional qualitative data on African American self-esteem development and insight into the possible characteristics of vacant esteem.