Using data collected by the Organization for Economic Co-operation and Development's Program for International Student Assessment in 2003, this study examines the gap in the educational aspirations of children from single-parent families and two-parent families in the United Kingdom (UK) and Hong Kong. Consistent with previous research on the relationship between cultural orientation and academic motivation, the analysis shows that children in the UK have statistically significant lower levels of educational aspiration than those in Hong Kong. Moreover, children from single-parent families in the UK and Hong Kong are found to have statistically significant lower levels of educational aspiration than those from two-parent families. Further analyses indicate that family capital and school experience are important factors for understanding the negative effects of single parenthood. Finally, the authors observe that single parenthood has a less negative effect on educational aspiration in the UK than it does in Hong Kong, which can be explained by differences in government family policy and family capital between the two regions. Based on the outcomes from the current analysis, the authors put forward several policy and service recommendations for improving children's educational aspiration and enhancing family well-being. (Published Abstract)