Family structure has been examined in depth for its possible impact on adolescent outcomes (such as substance use, achievement, sexual risk, etc.). Among the African American community, less than one-half of African American children live in two-parent households. African American households earn less than Hispanics and Caucasians, and they are less likely to be married than both Hispanics and Caucasians (Kreider & Elliot, 2009; NCES, 2003). The present study examined the level of association between family contextual factors (i.e., parent’s level of income, marital status, parent’s level of education) and adolescent outcomes (i.e., sexual activity, substance use, adolescent education) among an African American sample of adolescents ages 12 to 17. Using data from The National Longitudinal Study of Adolescent Health (also known as the Add Health Survey), N = 890, five hypotheses examined how positive family contextual factors have either a lower level or a higher level of association with the adolescent outcomes of sexual intercourse, sexual risk, substance use, educational aspirations, and educational performance. Results showed that two out of the five hypotheses were statistically significant. The study had varied outcomes for females and males. Specifically, the results showed that family contextual factors had an impact on the educational aspirations and educational performance of African American females. For African American males, parent's marital status had a negative association with substance use. Lastly, while 57% reported being sexually active, it was surprising to find a large number of adolescents, 37%, who reported not using birth control.