This thesis looks at the Late Antique mystical literary genre of Hekhalot alongside contemporary queer theory and modern psychoanalysis. Part 1 opens with an excerpt from "3 Enoch." The methodology is explained, and the relevant works of Sigmund Freud, Leo Bersani, and Georges Bataille are analyzed. These are then applied through a close reading of the "3 Enoch" text(s), with particular focus given to the microform of chapters 3-16. Part 2 describes the Hekhalot genre in greater depth, including its origins, the relationship it has with priestly and Rabbinic writers, and the questions that remain on how to situate this genre in relation to theoretical interpretations of mysticism and eroticism. The author describes literary themes of the genre, specifically looking at sexual and erotic overtones based on intense descriptive imagery, repetition, textual interruptions, and the use of hymns. These are examined in conversation with the writings of Luce Irigaray. In examining Hekhalot through the lens of queer theory and psychoanalysis the author observed the self-shattering nature of the texts. The climax is often the moment that the person ascending witnesses the divinity within the highest heaven yet at that moment there is a lack of clear, descriptive imagery indicating what Bataille would call "the place at which words fail." Heavenly ascent described in this literature is dangerous and self-shattering. Finally, the author provides conclusions and final reflections. The implications of examining Bersani, Bataille, and Irigaray together in light of the Hekhalot literature are discussed.