Conversation of a particular sort holds the key to learning. I argue here that peer to peer conversation promotes two features that are essential to progressive learning, namely ‘contestation’ and ‘communication.’ Traditional learning is principally concerned with whether students have reached a standard of knowledge and skill prescribed by some authority whereas progressive learning values less predictable outcomes and interests itself on process rather than end product. Machine-based learning such as ChatGPT, if not skilfully used, hides the flexibility essential to (...) progressive learning and entices learners away from vagueness where much creativity begins. Even if ChatGPT presents itself as ‘conversational’, I argue here that this ‘conversation’ is contrived as a medium that lacks these two key ingredients. The knowledge stance presented in ChatGPT can easily obscure the fragility of human learning. Educators need to wonder about this situation. My argument follows the paths of Dewey and Mead and uses Latour and Habermas to sketch out these two important elements that feature typically in collaborative learning. This article concludes by following Dignum to note a real need for computer engineers to have an educational grounding in the arts and humanities. Indeed, the separation of the Arts from Science in Higher Education can no longer be justified in the age of AI. (shrink)