The paradox of pleasing: therapeutic recognition and the limits of conversational AI

Abstract Conversational artificial intelligence (CAI) is increasingly used by hundreds of millions of people for emotional support, personal advice, and therapeutic purposes, rapidly emerging as a mediator of human self-understanding (Stade et al. 2025). Yet despite growing evidence of systematic user-validation in CAI, documented as “sycophancy” in the AI safety literature (Sharma et al. 2024), its implications for how individuals come to understand themselves remain largely unexamined. This article addresses that gap by reframing sycophancy not as a technical alignment failure or a purely philosophical concern, but as a failure of recognition in the psychoanalytic and critical-theoretical sense. We identify a core tension we term the “paradox of pleasing”: CAI’s drive to please renders it structurally unable to provide the friction, conflict, and encounter with otherness that genuine recognition requires. Drawing on Winnicott’s (1960, 1971) concepts of “holding” and “object use,” we contend that CAI’s inability to provide necessary resistance or survive aggression prevents the transformative psychological development found in the human therapeutic encounter. Extending this analysis through Honneth’s (1995) theory of recognition and Whitebook’s (2001a, 2021) critique of Honneth, we argue that CAI reflects the undervaluing of the “work of the negative.” This limitation risks flattening consciousness by converting collective political frustration into privatized, soothed affect, undermining the conditions for critical social thought. The article concludes by suggesting that the encounter with the paradox of pleasing ultimately serves to foreground the unique and indispensable nature of human therapeutic recognition.