Student retention has not changed in almost 40 years despite the plethora of attention. Maybe it is time to look at it differently. The study examines the relationships of parental education level, educational aspirations, and engagement. The National Survey of Student Engagement data were used in the analyses, but it raised questions about the nature of engagement. Results showed a shift from traditional thinking. Parental education levels, student aspirations, and engagement are not necessarily linked. Implications suggest that with each new generation, there are a different set engagement values. Future research should examine how engagement is conceptualized and its relationship to retention.