Computer-mediated intercultural exchanges among children are a mainstay of contemporary education and are often attributed to the advent of the digital and globalization age. But such exchanges are outgrowths of over a century of organized efforts, many led by the United States, to harness emerging communication technologies to promote cross-cultural dialogue among youth. Tracing the roots of pen pal correspondences—the Progressive-era, paper-based precursor to contemporary virtual exchanges—this chapter shows how an ideal of mediated intercultural exchange emerged and endured within educational and popular discourse from the Machine Age to the Digital Age. These grassroots, international exchanges of media texts among children not only constituted an influential form of global communication in the last century, but they also offered American educationalists, policymakers, and industries a durable trope for imagining the benefits of a world increasingly interconnected by technology.