The literature on the motivations and the impacts of remittances sent by international migrants to their families and communities strongly focus on their economic impacts and the flows of money from the global North to the South. The driving factors for remittance sending, closely embedded in motivations for migration, often overlook the conditions in which remittances are not sent, where households do not prosper, and community development does not happen. This ethnographic study uses the case of Nicaraguan migration to Costa Rica to examine the lives of the families of migrants in the context of rural to rural and South to South migration. The paper examines the intentions and realities of South-South migration through the lens of migrants and their families, and illuminates theother side of migration often invisible in the migrant’s home communities and the migration and development literature. The paper also shows the disparity in physical, economic, and emotional distance as it illustrates the unique structural challenges of South-South and especially rural to rural migrants. These structuralbarriers that create an unbridgeable distance between migrants and their families embody the chasm between the intentions and the realities of migration for individuals on both sides of the border.