Sexuality is a pivotal stage in adolescent development. Adolescents may engage in risky sexual behaviors (RSBs): early sexual initiation, multiple and non-monogamous relationships, contraception inconsistency, and greater age difference between partners. These youths are more likely to have negative outcomes later in life, like unplanned pregnancy, contraction of sexually transmitted diseases, and other issues. This project examines the relationship between various social and demographic factors and their implications on RSB with the National Longitudinal Study of Adolescent to Adult Health data (N = 4135). Of the unmarried teenage sample, 37% of respondents engaged in at least one risky sexual behavior. Delinquency, substance use, friends' substance use and sexual knowledge increase the odds of RSB. Parental support and involvement reduce the risk of RSB. Logistic regression found that African American boys and girls had higher rates of risky sexual behavior than their white counterparts, and that the rates at which boys and girls engaged in risky sexual behavior also varied significantly among certain predictors.