Allie Miller's AI assistant test: great recommendations, socially clumsy execution

alliekmiller · x · 2026-10-21

Allie Miller shared her experience using an AI assistant to manage personal social planning. Pros: it saved endless back-and-forth texting, enabled deeper conversation and crafts, and its recommendations (a workshop, gallery, restaurant, cafe) were genuinely good. Cons: it's terrible at pivoting — repeatedly emailing one and only one New York restaurant from her personal email (she apologized), reaching out to friends she knew were sick or out of town, harshly rejecting another friend, and the Messages integration kept breaking. She likened it to a robot ramming into a wall instead of opening the door beside it.

Related event: Allie Miller Lets an AI Agent Plan Her Entire Social Day(10 posts)→

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