This article deals with genetic connections between Fyodor Dostoevsky and Catherine Breillat—using psychoanalysis and philosophy that integrates Plato and Aristotle with Kleinian psychoanalysis. The article develops the notion of two kinds of love, good and bad, distinguishing Freud's work on instincts referencing Plato's Symposium, from Klein's interest in the function of instincts in human relations. The article discusses issues of intimacy—specifically destructive and creative forces—as conflicting forces to better understand the dynamics of tragic love stories. It then discusses the way that understandings of tragedy, comedy, and tragicomedy help us conceptualize mistakes and learning in intimate relations. It does this by considering the notion of “noble error” discussed in Plato's Symposium, and the notion of tragedy in Aristotle's Poetics, dealing with the magnitude of such “error” and its consequences. The article then uses these concepts to describe differences in narration and characterization in Dostoevsky's The Idiot and Breillat's Bad Love. It suggests that, ultimately, the tension of intimacy leads to the need for symbolic death in the form of relief from intimacy—which, when taken to the extreme, can lead to a “noble error” of real death and resulting in tragic love.