The other day, while I was rummaging through a stack of oldish articles on the future of the Internet, an obscure little essay from 1998 — published, of all places, on a Web site called Ceramics Today — caught my eye. Celebrating the rise of the “cyberflâneur,” it painted a bright digital future, brimming with playfulness, intrigue and serendipity, that awaited this mysterious online type. This vision of tomorrow seemed all but inevitable at a time when “what the city and the street were to the Flâneur, the Internet and the Superhighway have become to the Cyberflâneur.”

Intrigued, I set out to discover what happened to the cyberflâneur. While I quickly found other contemporaneous commentators who believed that flânerie would flourish online, the sad state of today’s Internet suggests that they couldn’t have been more wrong. Cyberflâneurs are few and far between, while the very practice of cyberflânerie seems at odds with the world of social media. What went wrong? And should we worry?

Engaging the history of flânerie may be a good way to start answering these questions. Thanks to the French poet Charles Baudelaire and the German critic Walter Benjamin, both of whom viewed the flâneur as an emblem of modernity, his figure (and it was predominantly a “he”) is now firmly associated with 19th-century Paris. The flâneur would leisurely stroll through its streets and especially its arcades — those stylish, lively and bustling rows of shops covered by glass roofs — to cultivate what Honoré de Balzac called “the gastronomy of the eye.”

While not deliberately concealing his identity, the flâneur preferred to stroll incognito. “The art that the flâneur masters is that of seeing without being caught looking,” the Polish sociologist Zygmunt Bauman once remarked. The flâneur was not asocial — he needed the crowds to thrive — but he did not blend in, preferring to savor his solitude. And he had all the time in the world: ...