Participation in risky sexual behaviors has many deleterious consequences and is a source of concern for parents as well as practitioners, researchers, and public policy makers. Past research has examined the effect of family structure and supportive parenting on risky sexual behaviors among emerging adults. In the present study, we attempt to identify the mediators that explain this relationship. Using survey data from a sample of over 2,000 college students (1,297 females and 780 males) we use structural equation modeling to investigate the role of commitment to marriage, desired characteristics in an intimate partner, and sociosexuality in linking the influence of family structure and supportive parenting to risky sexual behaviors. Results indicate that respondents from continuously married families were more committed to marriage, and this commitment reduced the probability of risky sexual behavior both directly, as well as indirectly through its negative impact on unrestricted sociosexuality. On the other hand, respondents who reported having supportive parents rated sensitivity and similarity of values as more important in a mate than physical attractiveness and sexual compatibility. This approach to mate selection reduces unrestricted sociosexuality and, in turn, risky sexual behavior. Even after taking our mediators into account, there is still a direct effect of family factors on risky sexual behavior. Gender differences in the pattern of findings are discussed and directions for future research are identified.