For generative AI to succeed, how engaging a conversationalist must it be? For almost sixty years, some conversational agents have responded to any question or comment to keep a conversation going. In recent years, several utilized machine learning or sophisticated language processing, such as Tay, Xiaoice, Zo, Hugging Face, Kuki, and Replika. Unlike generative AI, they focused on engagement, not expertise. Millions of people were motivated to engage with them. What were the attractions? Will generative AI do better if it is equally engaging, or should it be less engaging? Prior to the emergence of generative AI, we conducted a large-scale quantitative and qualitative analysis to learn what motivated millions of people to engage with one such 'virtual companion,' Microsoft's Zo. We examined the complete chat logs of 2000 anonymized people. We identified over a dozen motivations that people had for interacting with this software. Designers learned different ways to increase engagement. Generative conversational AI does not yet have a clear revenue model to address its high cost. It might benefit from being more engaging, even as it supports productivity and creativity. Our study and analysis point to opportunities and challenges.

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