But the gap between this theory and its execution was wide enough to march Kitchener’s Army through it. Google’s CEO Eric Schmidt had once said that the ideal was to “get right up to the creepy line and not cross it.” Unfortunately, by the mid-2010s, that line was being crossed constantly. While promising to be “helpful” or “thoughtful,” what was delivered was often experienced as “intrusive” and worse. Some ads seemed more like stalkers than valets: if, say, you’d been looking at a pair of shoes on Amazon, an ad for just those shoes would begin following you around the web, prodding you to take another look at them. What was meant to be “relevant” to your wishes and interests turned out to be more of a studied exploitation of one’s weaknesses. The overweight were presented with diet aids; the gadget-obsessed plied with the latest doodads; gamblers encouraged to bet; and so on. One man, after receiving a diagnosis of pancreatic cancer, found himself followed everywhere with “insensitive and tasteless” ads for funeral services. The theoretical idea that customers might welcome or enjoy such solicitations increasingly seemed like a bad joke.

Tim Wu, The Attention Merchants, loc. 1081