A distal psychosocial factor, perceived powerlessness, has been found to predict various sexual risk behaviors among youth, yet no studies have assessed mediators or moderators in this relationship. Using a demographically diverse, longitudinal sample of urban youth (N = 257), this study assessed whether the need for sexual validation mediates the relationship between perceived powerlessness and sexual risk behaviors and to assess whether this mediated pathway is moderated by socioeconomic status and gender. The mean age of the participants was 21 years old (range: 15–24) and the majority of the sample identified as Black (65%) and female (62%). The results of structural equation modeling showed that the need for sexual validation mediated perceived powerlessness and condomless sex at last sex among Black youth. The need for sexual validation mediated perceived powerlessness and concurrent sexual partnerships among White youth and depended on levels of socioeconomic status. Sexual risk behavior interventions should provide youth with increased opportunities that encourage feelings of validation from other personal achievements in addition to sex while simultaneously addressing the structural conditions that drive young people to feel powerless.