This paper investigates the relationship between sex and knowledge and its manifestation in the development of Artificial Intelligence. With the concept of the extimate uncanny I analyse the status of the robotic companion as emblematic of the Lacanian non- existent sexual relation. Through a commentary on the 2014 film Ex – Machina, I discuss the staging of symbolic castration, sexuation and the uncanny and suggest that this conceptual reading of the sex-bot is an essential starting point to a more complex understanding of the contemporary significance of Artificial Intelligence and sexualised automatons in the social bond. Via my reading, the figure of the sex-bot is understood to be the vanishing mediator which articulates the onto-epistemological nexus between psychoanalysis and philosophy.