Research suggests that children of single parents are at heightened risk of precocious sexual behavior, STDs, and other risky sexual outcomes. However, few such studies have addressed the type of single-parent family (single mother or single father), or differences across other-sex parent–child dyads. While gender essentialist models assume differences among youth living only with mothers or with fathers, constructivist models propose more flexible modes of parenting that lead to more similar outcomes. Using data from the National Longitudinal Study of Adolescent to Adult Health (n = 2570) on youth between the ages of 15 and 19, we compared sexually-related outcomes among adolescents, both boys and girls, who lived with a single mother or a single father. These outcomes include sexual intercourse and knowledge, use of contraception, attitudes toward intimacy and pregnancy, and diagnosis of sexually-transmitted diseases. The results from linear and logistic regression models indicated few differences between single-mother and single-father families, or between same-sex and opposite-sex parent–child matches, using p values of .05 or smaller. Our results called into question essentialist models that posit higher risks for adolescents living with a particular parent or with an opposite-sex parent.