Scant attention has been given to the consequence of actual weight status for adolescents' sexual wellbeing. In this article, we investigate the race-specific connection between obesity and risky sexual behavior among adolescent girls. Propensity scores and radius matching are used to analyze a sample of 340 adolescents aged 16-17 who participated in the National Longitudinal Survey of Youth Young Adult Survey in 2000 or 2002. Nearly even numbers of these participants identified as white and black (183 and 157, respectively). We find that compared to their non-obese white peers, obese white adolescent girls exhibit higher rates of multiple sex partners and sex with older partners, and are also less likely to use condoms. None of these factors are significantly related to high BMI within the black sample. These findings indicate that the negative social consequences of obesity extend beyond future economic and marriage outcomes to adolescent white women's sexual outcomes. They also highlight the importance of context: the implications of being obese during adolescence depend on cultural meanings of obesity.