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The role of a family environment in shaping the sexual behaviour of adolescents and young people (AYP) has been acknowledged in literature. This explanatory mixed methods study is aimed at highlighting the role of familial factors contributing to AYP pregnancy in Cape Town, South Africa, guided by the concept of Bowen’s Family Systems theory. Secondary data from the Cape Area Panel Study (CAPS) were analyzed, using descriptive and logistic regression procedures reporting odds ratios (OR). To complement the quantitative data, qualitative data were collected, using three (3) focus group discussions and 15 in-depth interviews. Results show that AYP who resided with a mother or father had lower odds of reporting an adolescent pregnancy compared with adolescents who did not reside with either parent. Lower odds of reporting a pregnancy were also noted in families who had an income of between 20,000 and 25,000 rands and above 25,000 rands. The results showed that both parent-child residence and high family socioeconomic status were protective against AYP pregnancy. Both AYP and parents perceived that pregnancy is largely due to family poverty which disempowers AYP from negotiating safer sex, and lack of parental monitoring due to work demands. Parents admitted that it was tough balancing parenthood and work, especially in single parent families, resulting in reduced monitoring.