TABLE OF CONTENTS

PRINT December 2015

Finn Brunton

Screenshot of log-in page for Ashley Madison, October 15, 2015.

THE STORY of the 2015 hack of the adulterous-hookup dating site Ashley Madison starts with a party in Manchester, UK, in 1950. It’s a hypothetical fete, imagined by the great mathematician, computing pioneer, and cryptanalyst Alan Turing, at which a game is played: You, the “interrogator,” are sitting at a teletype keyboard or something like it, chatting with a man (X) and a woman (Y). They’re both trying to convince you that they’re female; the object of the game is for you to guess correctly who really is. You ask: “Will X please tell me the length of his or her hair?” The man tries to pass as the woman; the woman tries to expose him. Turing’s twist on this game is famously known as the Turing Test: “We now ask the question, ‘What will happen when a machine takes the part of [X] in this game?’” This replaces the philosophical quandary “Can computers think?” with “Can computers pass as people?” Or, rather, can a computer pass as a man who’s trying to pass as a woman? Hold that thought.

The two massive dumps of private Ashley Madison data—including the identities of the site’s users—released by the hacker crew the Impact Team this summer read like a sprawling, nightmarish cross-century collaboration between Lydia Davis and Flaubert. Delusional e-mails, pie charts about emotional connections with software, fembot chat algorithms that are like erotic talk in a Twilight Zone episode, scrupulously absurd legal documents about “winks, private keys, and virtual gifts,” interaction-design flowcharts built on sexual entitlement, the desperate desire to forget and be forgotten: Think of it as the early twenty-first century’s great multigigabyte novel of infidelity, online identity, predatory business models, gender, and sex.

The basic structural outlines of our doorstop data-dump novel run like this: The Canadian company Avid Life Media owns a family of fairly depressing online properties with names like Cougar Life and Established Men; the flagship is Ashley Madison. It’s a site where married people can meet someone with whom to have an affair. ALM CEO Noel Biderman, a leopard-print golem brought to life by the phrase “There’s no such thing as bad publicity,” has leaned into the outrage this idea provokes; the slogan of the site is “Life is short. Have an affair,” and its advertising is deliberately excessive, made to be protested. ALM faces scandals (to address diversity concerns, they’ve presented hired models to the media as CEOs of their various properties), but nothing sticks. Then the Impact Team hacks into their servers and issues a demand: Fulfill your “Full Delete” promise to your users—to completely expunge the record of their profiles and actions on the site (for an additional fee, of course)—by fully deleting your site, or we’ll expose your data. Ashley Madison doesn’t flinch, the hackers release the gigabytes of data, and 2015 burns through its schadenfreude budget. People put their e-mail addresses—or their spouses’, parents’, friends’, those of celebrities and elected officials—into sites to see whether they’re in the Ashley Madison database. Bitcoin-based extortion schemes kick in, Biderman steps down, and class-action lawsuits grow on the horizon like thunderheads.

There’s nothing new—nothing terribly 2015—about the disclosure of infidelity. (Or the suspicion of same: Many accounts on Ashley Madison were created out of vague curiosity, or as a prank on someone else.) In fact, the one-on-one extortion we’re seeing around the AM user list is rather sweetly archaic in a time of NSA bulk-metadata capture: It’s artisanal blackmail, the old-fashioned kind of secret shame and exposure. What the hack can tell us about our current situation begins with that Full Delete promise that Ashley Madison made to erase user records on request. It’s a promise the company couldn’t actually fulfill, and they didn’t even try—designing a payment-based social site like theirs from which people can fully disappear is a considerable challenge—which incited the ire of the Impact Team and brought about the site’s doom. (It’s an all-sides moment of hypocrisy: A company for liars lies, and exposure on behalf of their customers sacrifices them as collateral damage to a public that simultaneously bemoans those customers’ loss of privacy, condemns them as cheating scum, and combs through their data looking for the good stuff.)

Full Delete is an appropriate last stage for what Ashley Madison, in fact, provided. The site gave the entire arc of a bad relationship without any actual relationship—the banal, predictable conversations; the fantasizing and the projecting; the guilt and the regret and the frantic effort to forget and erase the past—all as an automated service. After exchanges with mostly chatbot nonpeople about the most personal yet nonunique parts of one’s erotic inner life (selected from a short menu of predictable “looking for” and “turns me on” options), you can panic and pay to have it all nondeleted. It’s an operation run in bad faith all the way down the stack, from the boardroom e-mails about how to simulate more women on the site to the passwords created by customers, which—once you get past the usual “123456s” and “baseballs”—include memorable entries like “ishouldnotbedoingthis” and “donteventhinkaboutit.” The interaction design is beautifully assembled to help you noteventhinkaboutit: The account-creation steps don’t ask for money, using blurry backgrounds of the population of waiting ladies to carry you from one simple data-entry step to the next, like the gently curved chute that leads the cows to the skull-puncture machine. You even hear from a hot woman within minutes of signing up. “How r u?” she asks. “I’m sexy, discreet, and always up for kinky chat.” It’s only after you’ve written a reply, but before you can send it, that you first have to pay.

“You,” in this playthrough of the Imitation Game, are of course a heterosexual man, and Hot Lady #3863 is an automated profile designed to help reach “conversion,” turning a new account into a paying customer who buys credits in order to communicate with women. Internal records show that over the lifetime of the site, 80 percent of the first purchases on Ashley Madison were men trying to contact bots or read their messages. The actual female population of the site hovered at roughly 5 percent, with the company’s goal being to reach 11. “The profiles we create are not intended to resemble or mimic any actual persons,” wrote Ashley Madison’s corporate counsel about the bots. “As part of this feature, the profiles may offer, initiate or send winks, private keys, and virtual gifts.” As journalist Annalee Newitz’s painstaking analysis of the hacked Ashley Madison documents reveals, the tiny female user base didn’t matter much, because the bots were the heart of the business plan. They kept male users in the loop of paying to talk to an army of software instances of men’s versions of other men’s ideas of women. The sick joke in Abel Ferrara’s 1981 exploitation film Ms. 45 is that the angel-of-vengeance main character has been rendered mute by her traumatic experiences, and the men she encounters never even notice her silence, being more than happy to just talk about themselves until she finally plugs them. That the Ashley Madison bots converted any customers, ever, with their crude database of come-ons is an equally funny-cruel display of a male mental model of women, expressed as a few lines of code and a generic picture.

In this last plot point, our Ashley Madison data novel alludes, like all great works of fiction, to a longer history and a larger context, from Villiers de l’Isle-Adam’s 1886 classic L’Ève future (in which Thomas Edison builds a machine woman named Hadaly for his buddy, with gold phonograph discs in her body playing back dictation) through the RealDoll industry, the manic-pixie dream artificial intelligence of Scarlett Johansson’s voice in 2013’s Her, and Harrison Ford watching Sean Young’s pupillary response to inappropriate questions in 1982’s Blade Runner. (“Is this testing whether I’m a replicant or a lesbian, Mr. Deckard?” she asks.) One facet of misogyny and patriarchy—the project of treating women as things, in larger systems of domination—is making things that can stand in for model women, acting the way their male creators think women act.

Read against this background, the Ashley Madison data dump, like all too many works of fiction, only seems to be about women, men, fidelity, sex. It’s actually just about men: about what they think about themselves and about women, and about what they think they are owed. Forget the “Singularity,” that future moment augured by the Turing Test, when machines learning to pass as us will eventually surpass us and become smarter than people. This is the bleakest solution to the original Imitation Game: It doesn’t matter whether there’s a person (of any gender) or a machine on the other end of the line. The interrogator is only really interested in his own fantasies of sex and persecution anyway. Rather than what Ashley Madison promised—the dense nineteenth-century ménage novel of infidelity, marital secrecy, mistresses, and assignations—it delivered a really twenty-first-century romance: men and their algorithms, alone at last.

Finn Brunton is an assistant professor in media, culture, and communication at New York University.