Youth from single-parent families report lower educational aspirations than those from two-parent families. This study explored the influence of background factors (gender, grade, parental education and SES), parental involvement with education, academic self-concept, and peer influences on educational aspirations. The participants were Canadian adolescents; 2751 from two parent and 681 from single-parent families. ANOVA results showed that adolescents from single-parent families scored significantly lower than adolescents from intact families on educational aspirations, and other predictor variables. Hierarchical regression analysis showed that the pattern of relationships between educational aspirations and other factors was very similar for adolescents from both types of families; namely academic self-concept significantly predicted educational aspirations. The family involvement and background factors predicted educational aspirations via academic self-concept. Having academically oriented peers was especially beneficial to adolescents from single-parent families. Implications for intervention programs are discussed.