Past research has examined the widening gender gaps in college expectations and enrollment in the United States in which more women than men expect to continue their education and enroll in postsecondary institutions. A discrepancy exists between students' expectations and their enrollment behavior: more students expect to attend college than actually enroll. This discrepancy--effectively students' unrealized expectations and the commensurate gender gap--has recently gained the attention of the educational research community, but with inconsistent results. This inconclusiveness may be due in part to different operational definitions, assumptions, and/ or methods researchers have used in analyzing this phenomenon. Using 35 years of nationally representative data from American high school graduates and two operational definitions for unrealized expectations, we explore how the gender gap has changed over time by race and socioeconomic status. We find the two operational definitions of unrealized expectations yield results that differ in direction and magnitude. These findings demonstrate that operational definitions of fundamental constructs can change the results and conclusions and recommendations made, particularly as these relate to educational expectation formation and realization. The paper concludes by asserting the value of using multiple operational definitions to best represent the complexity of educational phenomena. [For "A Case Study to Examine Peer Grouping and Aspirant Selection. Professional File. Article 132, Fall 2013," see ED573093. For "Tracking the Discount: Tuition Discount Rates, Net Tuition Revenue, and Efforts to Inform Institutional Practices. Professional File. Article 133, Fall 2013," see ED573092.]