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The social science literature has shown that Latino/as lag behind Whites and Asians in college enrollment and completion. Latino boys fare even worse. In this paper, I aim to take a closer look at the Latina advantage among Latino/a millennials, those born after 1980. To do that, this study looks at both Latino/as’ high school experiences and their levels of social capital. Using the Education Longitudinal Study of 2002 (ELS: 2002), I learned that Latino/as, especially boys report worse high school experiences than their female counterparts. Specifically, Latino/as reported feeling less safe in their high schools, a perception that school rules are not applied fairly to all, and a lower likelihood of receiving academic recognition, even net of GPA. This study also finds that social capital does indeed vary by gender but, disconcertingly, it worsens between the foreign born and later generations, providing evidence for some generational decline among Latino boys and girls. Thus, this study takes an intersectionality approach to understanding the Latina advantage among Latino/a millennials. By taking into account not only gender and race but also generational status, the study provides evidence that Latino/as’, especially Latino boys’, relatively worse experiences during high school, might disincentivize their continuing on to higher education.