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Purpose. To investigate the possible positive cumulative effects that youth assets may have on youth sexual behaviors. Design. Cross-sectional data were collected from a randomly selected population by in-home, in-person interviews. Mantel-Haenszel chi-square test and logistic regression were conducted to determine the potential cumulative effects that youth assets may have on youth sexual behaviors and to test for significant asset by sexual risk behavior trends. Setting. Racially diverse inner-city neighborhoods in two midwestern cities. Subjects. Teenagers (n = 1350; mean age = 15.2 years) and parents of the teenagers (n = 1350). The response rate was 51%. Measures. Demographic factors, nine youth assets, and five sexual behavior outcomes. Results. Significant (p < .05) trends and odds ratios (ORs) were found for three of the five youth sexual behavior outcomes. Youths with more assets were more likely to have never participated in sexual intercourse (OR = 1.32). Of sexually active youths, those with more assets were more likely to have delayed first intercourse until at least 17 years of age (OR = 1.47) and to have used birth control at last sexual intercourse (OR = 1.18). Nonsignificant (p > .05) results were found for current sexual activity and number of sexual partners. Conclusions. The results generally support the notion that the more assets adolescents possess, the more likely they are to engage in positive behavior. Practitioners planning asset-based teenage pregnancy prevention programs might consider promoting several specific youth assets.