ABSTRACT. Objective. The purpose of the study was to examine the association between adolescents’ psychological distress and their sexually transmitted disease/ human immunodeficiency virus (STD/HIV)-associated sexual behaviors and attitudes. Method. Sexually active black adolescent females (N 522) completed, at baseline and again 6 months later, a self-administered questionnaire that assessed sexual health attitudes and emotional distress symptoms (using standardized measures, .84), a structured interview that assessed STD/HIV-associated sexual risk behaviors, and a urine screen for pregnancy. Results. In multivariate analyses, controlling for observed covariates, adolescents with significant distress at baseline were more likely than their peers, after 6 months, to be pregnant (adjusted odds ratio [AOR]: 2.0), have had unprotected vaginal sex (AOR 2.1), have nonmonogamous sex partners (AOR 1.7), and not use any form of contraception (AOR 1.5). Additionally, they were also more likely to: perceive barriers to condom use (AOR 2.2), be fearful of the adverse consequences of negotiating condom use (AOR 2.0), perceive less control in their relationship (AOR 2.0), have experienced dating violence (AOR 2.4), feel less efficacious in negotiating condom use with a new sex partner (AOR 1.6), and have norms nonsupportive of a healthy sexual relationship (AOR 1.7). Discussion. The findings suggest that psychological distress is predictive over a 6-month period of a spectrum of STD/HIV-associated sexual behaviors and high-risk attitudes. Brief screening to detect distress or depressive symptoms among adolescent females can alert the clinician to the need to conduct a sexual health history, initiate STD/HIV-preventive counseling, and refer for comprehensive psychological assessment and appropriate treatment. Among adolescents receiving STD treatment,those with even moderate emotional distress may be at heightened risk for further unhealthy outcomes. STD/ HIV interventions should also consider psychological distress as one potential risk factor that may impact program efficacy.