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The results of this analysis show that there is a notable relationship between a mother’s risk-taking behavior, as expressed through drug use and unprotected sex, and her child’s external behavior, particularly as it is expressed through the child’s self-reported risk-taking attitude. This relationship is most evident when considering the mother’s marital status, employment, educational attainment, number of children, and the child’s age. After examining this relationship further by studying female and male children behaviors separately, it appears that there are important differences for male and female children in terms of the effect of mothers’ risk-taking activities on their external and internal behavior. For male children, the mother’s risk-taking activities had a negative impact on the change in their depression status and a positive impact on their participation in illicit activity, both results of which were marginally significant. For female children, there appears to be no reliable relationship between their internal or external behavior and the mother’s risk-taking behavior, which may be because female children are less likely to commit criminal acts (relative to males).