Classical psychoanalysis has been used as a form of literary criticism for getting “behind” a work’s surface to its unconscious “meanings.”. Vladimir Nabokov, who famously derided psychoanalysis, wrote Lolita in part to satirize analytic interpretations. Lolita achieves a paradox where the prose of the story’s confessing pedohebephile, Humbert Humbert, leaves readers enthralled by his storytelling and disturbed at deriving pleasure from the deplorable content. The paradox renders critical interpretive neutrality impossible, as reducing Humbert to the sources of his pathology denies one’s own alterity as a disgusted/enthralled-witness to his storytelling. Worse, this interpretive approach reproduces Humbert’s own manipulative violence by flattening both protagonist and experiencing reader to nothing more than gratifying objects of fantasy; just as Humbert, by failing to recognize the subjectivity and alterity of Lolita, uses her as his own gratifying fantasy object. The authors argue for a “meaning behind”Lolita located in the troubling cavern of alterity of oneself-as-reader, which requires confessing the multiplicity of stirrings aroused by the book. The authors eschew the classical analytic approach in favor of critical dialogue with Lolita informed by intersubjective and relational theories, to access Humbert as a fragmented mirror of self and explore the problematic terrain between aesthetic enjoyment and moral complicity.