The essay gives an overview of European practices of bi-personalisation. The modern literary medical phenomenon of the double is distinguished as a separate historical case and the type of psycho-cultural disassociation, is contrasted with premodern doubleness. The author does not believe that mythical and ritual duality encompasses the specifics of literature, and in this regard, the author argues against the structuralist approach to doubling, as well as with other related approaches. It is noted that the reflective suffering of the hero confronts a primitive ritual lycanthropy and is able to block the game of binary oppositions in the ancient novel (“The Golden Ass” of Apuleius). However, to consolidate the literature on doubles one needs other socio-cultural conditions than existed in premodern times. To draft historical types of disassociation, the author introduces the concepts of polypsychism, psychocracy, and anthropo-cultural formation. The stories of the Doppelganger and mesmeric experiments are taken in their common mission of disenchantment with the world and the centralization of pre-modern plurality. The cycle of the pair - “polypsychism – monopsychism” is studied in the religious and secular versions. The main device of literature about doubles is defined as the transformation of all nodal points of the system of storytelling, its compositional structure, plot twists, the ideological and psychological characteristics of the heroes, and the epistemological junction of authenticity and fiction into the figure of the Other. The contemporary praxis of bi-personalisation is formed at the interface between two civilization orders (or anthropocentric formations). The demonic resource of the past is picked up by the fiction while it is being excluded from law, government, politics, academiс science, and other powerknowledge spheres and enters into the sphere of fantasy. From Gothic “black” thrillers of the XVIII – early XIX centuries to the symbolism and modernism of late XIX–XX centuries, literature about doubles changes, but preserves the device of bi-personalisation of structural-composite nodes in the range from “demonism” to the sophisticated game of the author within the narrative instances of the text.