OpenAI's Will DePue on Why AI Chat Feels Flat: No Interruptions, No Edited Messages, and Models Aren't Funny

willdepue · x · 2026-09-22

OpenAI's Will DePue sparked a discussion with Nat Friedman about why AI experiences boomed then disappeared—AI Dungeon was massive, Character AI has faded—and why models "aren't funny," which he finds bizarre given how creatively weird GPT-3 chat was.

His critique of the chat format:

He argues the entire chat interaction paradigm needs rethinking, contending current product design boxes in what models can do.

Related event: OpenAI Staff Question Why Chat AI Lost Its Fun and Flexibility(2 posts)→

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