Precursors to adolescent health-risking sexual behavior (HRSB) were examined in a normative sample of 373 adolescents (48.0% female, n = 178). Using a variable-oriented approach, we regressed the number of sexual partners at high school exit (age 17) on parental monitoring, association with delinquent peers, romantic relationship status, problem behavior, physical maturity, and tobacco and alcohol use at high school entry (age 14); all emerged as significant predictors except alcohol use and physical maturity (we found sex differences in physical maturity and romantic relationship status, with females being more advanced in both areas). Sexual experimentation at high school entry served to partially or fully mediate the impact of these factors. A person-oriented approach, using a broader measure of HRSB, found three subgroups of adolescents: abstainers, low-risk-takers, and high-risk-takers. Results predicting membership in these groups generally followed those from the variable-oriented analysis. Implications for the prevention of HRSB and future research directions are discussed.