Human immunodeficiency virus (HIV) interventions can significantly reduce risky sexual behaviors among vulnerable populations. However, not everyone exposed to an intervention will reduce their sexual risk behavior. This qualitative study sought to identify factors associated with young African American females' lack of increase in condom use post-participation in an HIV prevention intervention. Semi-structured interviews were conducted with 50 young African American women (18-23 years; approximately half were mothers) after participating in a demonstrated effective HIV prevention intervention; 24 did not increase condom use post-intervention. Interviews were thematically coded for barriers to condom-use post-intervention. Although nearly all young women reported partner-associated challenges to using condoms, there were relational differences observed among those who changed their condom use versus those who did not. Many "non-changers" were engaged in non-stable "on and off" relationships, with high rates of infidelity, often with the father of their child, in which they were fearful of requesting condom use. "Non-changers" also reported more substance use, feeling incapable of change and not thinking about condom use. Thus, future HIV prevention efforts may benefit from incorporating strategies on how young mothers can maintain a non-sexual relationship with their child's father, as well as elaborating on the intersection of substance use and risky sexual decision-making.