Data were collected on arrested youths processed at a centralized intake facility, including youths released back to the community and those placed in secure detention. This paper reports the results of a test of a structural model involving newly arrested male and female youths' sexually transmitted diseases (STD) test results, urine analysis results for recent cocaine and marijuana use, and self-reported engaging in risky sexual behavior. The across gender, multiple group model involved: (1) a confirmatory factor analysis of these variables, reflecting a latent variable labeled Risk, (2) a regression of Risk on the youths' age, and (3) an examination of the covariance between Risk and the youths' race and seriousness of arrest charge. Results indicate the youths' STD status, drug use, and reported risky sexual behavior are interrelated phenomena, similarly experienced across gender. Age was the only correlate of Risk status that demonstrated a significant gender group difference. The youths' race and seriousness of arrest charges did not significantly affect Risk, regardless of gender. Research and policy implications of the findings are discussed.