I‘m being stalked by a pair of cheap eyeglasses. They keep looking out at me with their eyeless stare. They’re joined by a zombie pair of khakis, Hillary Clinton, and, creeping along on their spindly little legs, folding music stands. None of them will leave me alone.
This is not a Tim Burton movie, but my daily experience surfing the web. Wherever I go on the Internet, I’m followed by advertisements for things I don’t want. Yes, I know it means I need to clear out the cookies clogging up my computer, those electronic markers that allow advertisers to track me. That said, I’m astonished at how clumsy, obvious, and off-puttingly persistent these ads are.
Internet advertising wasn’t supposed to be this way.
The promise was that, sifting through oceans of data created by our online activities, computers would be able to predict our likes and wants, using those predictions to shape our behavior. Our devices, calculating opportunities to interest us in products and services, would subtly nudge us, presenting those products and services at just the right moment—whether that moment was defined by proximity to a store or psychological vulnerability to a pitch.
In practice, the electronic Mad Men only seem to be pitching to me exactly what I’m least likely to buy—things I’ve already looked at, considered, and rejected. If I had wanted those khakis, I would have bought them when I first had them up on my screen. I went to the cheap glasses site merely to check a fact in a writer’s story on cheap glasses. I clicked on two or three pairs to confirm the prices the writer had cited. Now, months later, hardly a day goes by when I’m not presented with an online ad for crap eyewear.
Once, I clicked on a Hillary ad to see what kind of spiel her folks were currently making. (The things one does in the name of journalism.) Hillary’s algorithm thinks that click means I’m a lead, and her bots have been determined for months to close the deal. Today I get a banner blaring “I’m With Her” at the top of the New York Times homepage. (Then again, it could just be advertisers assume anyone going to nytimes.com is a Hillary lead.)
A couple of weeks ago I looked at a half-dozen folding music stands online. I clicked away without buying any of them. The Chicago Tribune, Slate, and the St. Louis Post-Dispatch all think I just need another look. Like many other websites have in the last week, they are showing me half a dozen folding music stands that I don’t like the look of.
Why does the web keep flogging the very things I’ve demonstrated I don’t want? It’s a mystery, but I do have a theory. Well, two theories.
Theory No. 1 posits simply that online advertisements aren’t any good. The coders have their limitations, and among them is an inability to work any fancy anticipatory magic. The best they can do is hassle us about the stuff they’ve logged us looking at already. “Hey, mister!” the online pitchman wheedles and whines, grabbing our sleeves long after we’ve left the electronic store: “Hey, mister!!”
But given how grand the promises were, and the amazing things that the devices demonstrably do, is it really possible that online advertising is that lame? Could it really be that, after claiming to be able to intuit our deepest needs, all the devices are able to do is pester us about what we’ve already rejected?
Our machines know where we are at all times and most of what we’re up to; they know who our friends are, what those friends are up to. Maybe the devices do know our needs and wants better than we know them ourselves and are using that knowledge to move us in ways that are profitable for the devices’ advertising clients. But surely, then, the masterminds of digital advertising are savvy enough to know this is deeply creepy. Which brings us to Theory No. 2: They paper the web with obvious, preposterous ads—the zombie khakis and Hillary—as a ruse to make us think that’s the best they can do, thus providing cover for the hidden, clever calculations deftly, surreptitiously, and relentlessly manipulating us.
Theory No. 2 is more fun to contemplate, as conspiratorial fantasies always are, but Theory No. 1 seems more plausible to me. To believe the second theory, you have to posit that our computer overlords are evil geniuses. All you have to believe, to credit the first theory, is that the digital ad-guys are frauds. I think that’s more credible, Occam’s-razor-wise.
Of course, now that I’ve written that, just watch me get months of online ads for shaving supplies.

