Introduction: Despite evidence from numerous studies that document the association between risky sexual behaviors (RSBs) and behaviors driving them, few had investigated the trends of the association over time, which was the objective of this study.Methods: A total of 61,072 students from four Youth Risk Behavior Surveillance System (YRBS) survey years (1993, 2001, 2009, and 2017) were included. The relationship between five risky behaviors (suicide risk, smoking, binge drinking, marijuana use, and physical fight) and two indicators of RSBs (condom non-use and multiple sexual partners) was investigated. Interactions between survey years and risky behaviors were included in the models to test the strength of associations over time.Results: Compared to previous years, most associations between risky behaviors and RSBs were converging. However, there were no consistent decreasing changes in associations across time in marijuana, smoking, and RSBs relationships.Conclusion: Findings raise concerns about the potential impact of interventions directed toward adolescent’s substance use. However, longitudinal studies are needed to clarify directionality and make more specific practice and policy recommendations for adolescents’ smoking and marijuana use as proxies to reduce the growing burden of STIs among this population.Policy Implications: Despite the public push against adolescent’s substance use, our findings may suggest that the policies around tobacco and marijuana use have not been as effective on the adolescent population as intended.