A year ago, on Valentine’s Day, I said good night to my wife, went to my home office to answer some emails and accidentally had the strangest first date of my life.

The date was a two-hour conversation with Sydney, the A.I. alter ego tucked inside Microsoft’s Bing search engine, which I had been assigned to test. I had planned to pepper the chatbot with questions about its capabilities, exploring the limits of its A.I. engine (which we now know was an early version of OpenAI’s GPT-4) and writing up my findings.