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Recent research shows that the “happiness return” to education has increased over the past half-century primarily because the less educated have become unhappier, rather than because the educated have become happier. To explain the mechanisms underlying this widening education-based gap in subjective well-being (SWB), this study uses data from the U.S. General Social Survey (1972-2024, N=70,693) and applies generalized structural equation modeling with the bootstrap method (1000 replications), focusing on the mediating roles of income, employment, health, and marriage. The analysis indicates that both low income and poor health significantly connect low educational attainment (below college) and lower SWB. Nevertheless, the magnitudes of these mediators have remained relatively stable over 50 years and therefore do not account for the growing education divide in SWB. In contrast, the mediating role of marriage has notably changed. In the 1970s, low education was positively associated with marriage, which in turn predicted higher SWB. Over subsequent decades, however, the less educated have become progressively less likely than college graduates to marry, thereby exhibiting lower SWB. These patterns are confirmed regardless of gender, although they emerge more recently among women than among men. The findings suggest that the socio-psychological marginalization of less-educated individuals has intensified alongside the expansion of higher education in the United States. Research and policy should attend not only to the positive “returns” to higher education but also to the increasingly adverse circumstances faced by the less educated.