Any high school student will admit that their friends are very important to them. But how much do friends make a difference in students\u27 lives, especially with regard to their school outcomes? Past research indicates that individual and structural characteristics alone do not explain the educational gap; closely examining the role of school friendships provides a promising new approach to this troubling issue. My dissertation demonstrates that best friends mediate the relationship between individuals\u27 background characteristics and school settings, structuring how the student adapts and performs in school. I develop an integrated theoretical framework that considers the characteristics of students (and their families), the educational institutions they attend, and their closest social ties at schools-their best friends. The data for my dissertation comes from the National Longitudinal Study of Adolescent Health (Add Health), a nationally representative study of adolescents in U.S. schools. My dissertation focuses on the relationship between friendship choices and school outcomes, comparing white adolescents with Hispanic youth of diverse ethnic origins. The principal questions addressed are: How do best friends of Hispanic adolescents shape their educational experiences? And, are there differential benefits from their friendships for Hispanic students compared to White students? Hispanics are the largest minority in this country, are growing at a faster rate, are younger on average than the general U.S. population, and they continue to migrate to this country. Most worrisome is that Hispanic high school students are becoming the most disadvantaged group in the U.S. and have the highest high school dropout rates and lowest schooling rates of any racial/ethnic group. Still, studies comparing white and Hispanic youth are scarce. My dissertation demonstrates that friendships provide important resources that reflect on the educational outcomes of the individuals. In addition, my findings support the claim that Hispanics are a heterogeneous group and this is manifest in both their friendship choices as well as their educational outcomes