Gender gaps in educational expectations and postsecondary enrollment are well studied, but few scholars have investigated the extent to which students realize or fail to realize their expectations. Even fewer have examined how the likelihood of realizing one's expectations may differ for men and women. Using 35 years of data, this study examines the role race, social class, and significant others' influences have played in realizing educational expectations and how these relationships have differed for men and women. It also investigates how group gender differences in these characteristics have contributed to the gap between the proportion of men and proportion of women who have realized their educational expectations via college enrollment. Results show trends in realized expectations by gender over time. Group gender differences explain little of past gaps but returns on students' characteristics differ by gender, which has been a key explanatory factor for differences between men and women in realizing their expectations. Implications of these findings relative to policy and program initiatives are discussed.