Theodore bonded during the years of his coemperorship with a close circle of companions. He called them his “friends,” using a range of Greek words.1 A scrutiny of this microcommunity at the court reveals aspects of his daily life and sheds light on the formation of his character, while exhibiting the network of individuals around him. Examining his companions at court also provides the background necessary to make sense of his confrontation with the top tier of the aristocracy and leads to a clearer understanding of his political and moral philosophy. The crown prince came to view friendship as a fundamental human value and a pervasive sociopolitical phenomenon. His interest culminated in a treatise on the role of friendship in society that he addressed to his long-term companion George Mouzalon. This special work represents the only articulation in Byzantium of a coherent theory of friendship, yet it is something of a conundrum. His investigation of friendship is as much theoretical as personal. A look at the profiles of his friends and foes illuminates both his promotion of what he called “friendship” and the political positions that he took as a reigning emperor.