Parental expectations have long been studied as a factor in increasing adolescent educational aspirations, often linking these expectations to parental level of education and involvement in academic endeavours. This study further explores this relationship in a statewide Midwestern sample of parents and their adolescent children. Regression analysis and independent samples t-tests were used to predict adolescent aspirations and compare groups. Results suggest that adolescent educational aspirations can to some degree be predicted by parental expectations. Parents reported high expectations for their children despite low levels of personal educational attainment. However, these high expectations were buffered by a reported unfamiliarity with college requirements and an expressed concern about college affordability and limited awareness of financial aid opportunities. Limitations and suggestions for future research and intervention are discussed.