Research on family contexts and adolescent sexual risk behavior has largely neglected relational aspects of sexual risk, such as having sex with strangers. The present study uses the NLSY97 to examine associations between sexually active adolescents' sex with strangers and parental monitoring, support, strictness, and household structure. More than 12% of the sample report having sex with a stranger within the past year (19% of boys and 5% of girls). Generalized estimating equation models indicate that high monitoring and strictness may have protective effects for risk of sex with strangers, whereas inconsistent parenting styles and living in biological-father/stepmother homes may increase this risk. Boys appear to respond more strongly to parental strictness than girls, and mothers' parenting processes may matter more for risk of sex with strangers than fathers'. These findings suggest there are gendered ways that healthy family contexts might reduce adolescents' risk of sex with strangers.