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This study focuses on the disparities between the educational aspirations and expectations of pre-college students in the United States, and explores what makes “unfulfilled aspirations” among those who aspire to obtain postsecondary degrees. Using a large national dataset and logistic and multinomial logistic regression, the current study examines the influential factors relating to why some students who want to go to college do not feel that they will be able to do so. Additionally, we explore whether students with concerns about reaching their college aspirations are less likely to apply or enroll in college. This study gives scholars and practitioners new ideas and information relevant to interpreting students’ educational aspirations, expectations, and the disparities between them.