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This document describes an evaluation of how various AI assistants handle empathetic conversations. The AIs evaluated include Claude, Gemini, ChatGPT, Willow, Pi.ai, Mistral, and a customized version of Claude. Each AI was prompted with scenarios involving being sad, happy, or having nightmares. Their responses were assessed based on expression of sympathy, attempts to understand the user, provision of space for emotions, advice quality, affirmative...