What is the relationship among migration, education, and socio-emotional well-being? This article draws on ethnographic research with Dominican youth to examine the impact of maternal migration on young immigrants and their educational aspirations. We detail how the youth come to conflate mother love, the sacrifices of migration, and educational investment. We argue that this conflation represents a "cruel optimism" (Berlant 2011), wherein the impossible object of desire--social mobility through schooling--impedes well-being.