Recent research on “psychotherapy” in Greek philosophy has not been fully integrated into thinking about philosophy as a way of life molded by personal relationships. This article focuses on how the enigma of Socratic eros sustains a network of thought experiments in the fourth century BCE about interpersonal dynamics and psychical transformation. It supplements existing work on Plato's Symposium and Phaedrus with comparative material from Aeschines of Sphettus, Xenophon, and the dubiously Platonic Alcibiades I and Theages . In order to select and illuminate commonalities among all of these, it also draws critically upon Jacques Lacan's psychoanalytic technique and his numerous comparisons between Socrates and psychoanalysts. What emerges is a more complex and qualified but no less sincere appreciation for the ideal of reflective, cooperative aspiration toward Beauty portrayed in Plato's dialogues.