This article explores the educational experiences of 93 young women who experienced pregnancy at school in England, in order to examine the relationship between dislike of school, teenage pregnancy and educational disengagement. The article argues that a strong dislike of school, pre-pregnancy, is often at the root of disengagement before pregnancy, a situation often exacerbated when the news of pregnancy is met with prevailing negative attitudes within school. However, once pregnant, educational alternatives to school frequently provide a route back into, and a changed perception of education. Tackling pre-pregnancy dislike of school may have important implications for both the support and prevention aspects of the Government's teenage pregnancy strategy.