This chapter introduces the human as a question. It revolves around the figure of the Theban Sphinx and her interaction with Oedipus and traces her presence from the ancient world into the works of Sigmund Freud. The chapter invokes the Sphinx as a presence that both prompts and challenges the way we think the human. Oedipus’ troubled humanity stands at the intersection between his success in solving the Sphinx’s riddle and his apparent failure to understand how her words apply to his own existence. As such, the Sphinx’ intervention at Thebes exposes a deep-seated vulnerability at the core of the human condition – a vulnerability springing from the fact that while the riddle can be solved with the powers of reasoning, the human as a riddle remains enigmatic and beyond the application of logos.