This thesis comprises a creative piece in the form of an experimental novel aiming to explore the implications of a near future in which literary meaning and bespoke written sentiment is generated cheaply, immediately and in concert with state-industrial networks of surveillance data. Besides this sits a critical component that aims to develop an account of literary meaning as such in light of this new technology. I argue that an interrogation of the method through which Generative AI functions by way of Jacques Lacan shows how the synthetic generation of textual meaning reveals what Slavoj Žižek calls the ‘indeterminacy paradox’ in uniquely contemporary relief. This crucial paradox, I argue, mirrors a central preoccupation in recent canonical contemporary Anglo-American fiction and its mutually paranoid relationship with ‘critique’. Comparing the renderings of orphanhood, illusion and truth in Kazuo Ishiguro’s Never Let Me Go and David Foster Wallace’s Good Old Neon I argue that both writers’ ‘début du siècle’ work point towards the necessity of the others’ positions across what might be an unbridgeable divide. This gap comprising, I argue, a historically novel suspicion of language as a necessarily fictive medium and of the mechanisms of illusion and indeterminacy at the heart of fictional meaning. I frame my creative piece as an attempt to enact the dramatically alienated and technologically accelerated end-point of a subjectivity and an art form which, unable to shake said suspicion, can no longer sufficiently commit to itself.