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This paper examines shifts in future orientations across three generations of Midwest families. We draw on a unique data archive from the Youth Development Study, including 266 G1-G2 parent-child dyads and 422 G3 children, to assess change over the past two decades in parental expectations about their children’s educational attainments and adolescents’ own outlooks for the future. We assess G2 and G3 adolescents’ aspirations for socioeconomic attainment, their academic self-esteem, their expectations across multiple dimensions of the life course, the obstacles they perceive to their career progress, and whether they think their lives will turn out better for them than their parents. Despite concerns that the “American Dream” is eroding in the face of labor market restructuring and the recent Great Recession, parents’ (comparing G1 and G2) educational aspirations for their children, as well as children’s (comparing G2 and G3) own socioeconomic aspirations, have increased. Upward shifts across generations in future outlook, however, are more pronounced among adolescent girls than adolescent boys. Compared to their parents (G2), observed at the same age, teenage girls (G3) have more positive life course expectations, they think their lives will turn out better for them, they have higher academic self-esteem, and they expect less career interference from sex discrimination and work-family conflict. No significant differences in future outlook were found for adolescent boys and their parents, as adolescents.