The relationships between literature and diplomacy are plural, ancient, and reciprocal. This entry examines the history of those relationships from the fourteenth century to the present day, from the end of feudalism and the birth of humanism, and the ambassadorial practices attendant upon each, to present‐day international relations and literary responses to diplomatic handling of global terrorism. The entry focuses in its first section on the figure of the author‐diplomat, turning to the products of those figures in the second section, which considers representations and imitations of diplomats, diplomatic process, and diplomatic rhetoric. Genres of literary diplomacy are suggested (for example, lyric, dramatic, romantic) in order to trace specific traditions of representation.