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This paper examines international correspondence—the friendly exchange of letters between ‘pen pals’ in different countries—as a form of grassroots media practice that was widely used in the late 20th century to make sense of the educational, democratic, and social possibilities of the early Internet. Drawing from educational and press reports, it first documents the enthusiasm over “e-Pals” websites and online correspondence programs used by American and foreign schools in the 1980s and 90s. Second, it situates these reports within a broader framework of public discourse about international correspondence in American education and culture from the early 20th century. Drawing from this history of pen pals to e-Pals, the paper proposes that intercultural media exchange has become a recurring and durable trope for discussing the utopian educational values of new media innovations. From radio to tape recorders to computers, the practice of ordinary people (particularly youth) relaying friendly mediated messages across geographic and cultural boundaries has provided a point of recurring public interest in and optimism for new communication technologies, particularly against a backdrop of geopolitical tensions and increasing cultural and economic globalization. This study contributes to communication history scholarship by underscoring the global and cultural dimensions of utopian claims that often surround emerging communication technologies. Furthermore, it contributes to research on contemporary media cultures by highlighting an overlooked tradition of grassroots, global communication that informs today’s “social web.”