CHAPTER 7. NICHES

“Greed is all right,” the legendary stock trader Ivan Boesky told the graduating class at Berkeley’s School of Business Administration. “I think greed is healthy. You can be greedy and still feel good about yourself.” This was in May 1985. A lot had changed since protestors paralyzed the campus twenty years earlier. The student radicals of the 1960s had insisted that they had a right to conduct their private lives as they saw fit. By the 1980s, however, Berkeley students took for granted that they could sleep with whom they wanted, when they wanted. They were less interested in free love than in high finance.

The screenwriters for Oliver Stone’s movie Wall Street lifted the most famous lines of the antihero Gordon Gekko directly from Boesky’s Berkeley commencement speech. Gekko, played by Michael Douglas, is engineering a hostile takeover of a family-owned paper company.

“Greed, for lack of a better word, is good,” he tells a room of wavering shareholders. “Greed, in all of its forms; greed for life, for money, for love, knowledge, has marked the upward surge of mankind.”

By the time Wall Street came out in December 1987, the stock market had collapsed, and Boesky had been convicted of insider trading. He would pay $100 million in penalties, serve a three-and-a-half-year prison sentence, and be barred from working in securities for life. But his mantra Greed is good has stayed in the American lexicon. The more surprising phrase that Gordon Gekko coined, greed for love, never caught on the same way.

There was always something a little tongue-in-cheek about the decadents who crooned, as Madonna did, that the boy with the cold hard cash is always Mr. Right. But in the late 1970s and early ’80s, shifts in the American economy did begin to turn marriage into a luxury good. The sense that only upper-middle-class and wealthier, college-educated people could manage to get and stay married dramatically changed the landscape of dating. So, too, did another important idea that the ’80s bequeathed us. If greed was good, desire works best when it is specific.

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Romantics tend to associate love with serendipity. They wait for what the French call the coup de foudre, to be stricken by a lightning bolt of attraction. But realists recognize the advantage of strategically cornering the dating market. In order to do it, you have to know your niche. All algorithm-driven dating services rely on the premise that with good enough data, they can match anyone to his or her soul mate. But in order to use these services effectively you must first narrow your search terms.

Since the era of the Shopgirl, the “likes” that daters use to telegraph their personalities have multiplied and become more precise. A friend recently admitted that he had found his last girlfriend by searching OkCupid for W4M in the New York area who had liked Alice Munro. He had planned to go on dates with each of the five results but then hit it off with the second; they were together for four years. I was surprised that the Munro search turned up only five straight women. After all, she is a Nobel laureate. “Oh yeah,” the friend said, and then confessed that he had started with other authors, whose names had not culled his prospects as effectively. “I like David Foster Wallace. But if you type David Foster Wallace into OkCupid, it’s a shitshow.”

In order to appeal to prospective lovers, you must know where to look. You must learn to brand yourself so that you will be searchable by the right people, too. The dating website How about we … relies on the idea that you will get along well with someone to whom your spontaneous flights of fancy appeal. Users propose dates, which then appear in the feeds of other users; if you want to do something someone proposes, it puts you in touch. Successful daters, on this site, must master a push-pull between quirkiness and conformity. You won’t get many bites by posting, How about we go to a movie? But neither will How about we play Mario Kart at my place while eating leftover Ethiopian takeout and then laugh at how flatulent it makes us? Even though, with the right person, doing either of those things sounds fun.

Scott Kominers, a visiting scholar at Harvard Business School who teaches about online dating in his courses on market design, explains why the signals that singles send to one another through dating sites and apps tend to diverge. The push-pull effect between suggesting a movie and Mario Kart is the result of competing tendencies toward “pooling equilibrium” and “skewing,” or “polarization.”

The first effect explains why so many dating profiles look so boring. For instance, why does almost everyone profess to love travel?

“When there are high costs associated with providing a certain response that is perceived as unusual, people will tend toward giving answers that they see other users give—answers that are average,” Kominers says. For instance, someone who puts down “math rap” under interests can immediately turn off many other users on that basis.

“If I’m a heterosexual man who has listed one of the high-cost responses and not many women I am interested in are responding to my messages, I go and try to find out what other guys are putting. And I see that they said ‘travel’ and that they did not mention anything as nerdy as math rap. And I think to myself, ‘Well, travel’s okay. I don’t dislike traveling.’ So I add travel to my interests in the hopes of having greater success.”

Eventually, however, the pooled equilibrium can inspire the opposite effect. Users who find themselves flooded with average profiles or feel lost in the sea look for signals to differentiate themselves. According to Kominers, “skewing is an effect of the site, a consequence of and reaction to the fact that everyone looks the same.” Over time, the process leads to the multiplication of niche services like FarmersOnly.

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The dream of finding your other half, the one custom-made just for you, is an old one. In Roman mythology, the lonely sculptor Pygmalion spends his days creating a statue of his ideal woman. The goddess Venus eventually takes pity on Pygmalion and brings his marble girl to life. They get married and live happily ever after. The 1980s version of this story is the John Hughes movie Weird Science, about two high school geeks who conjure up their dream girl. They are inspired not by Venus but by watching the 1931 movie Frankenstein on cable. Instead of stone and chisel, they use a desktop computer, which they connect with wires to a bunch of magazine cutouts. The Frankenbabe who emerges is a little grown-up for them. But by conjuring a cool car out of thin air, and helping them throw wild parties, she raises their social stock to the point where they can score cute human girlfriends.

Weird Science was science fiction, and it was meant to be funny. But today the Internet dangles out the tantalizing prospect that any man or woman could actually almost do this. Now any of us might dream of becoming Pygmalion 2.0.

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On the surface, the beginning of the Era of the Niche looked very different from the free love years that preceded it. When Ronald Reagan first ran for governor of California in 1966, he had promised to get rid of the “Berkeley bums.” During his first campaign for president, in 1980, he scored points with conservative supporters by expressing contempt for hippies who (he said) “act like Tarzan, look like Jane, and smell like Cheetah” and indulge in “orgies so vile I cannot describe them to you.”

Most Americans seemed to agree that the free-for-all of the sexual revolution had gone on long enough: Reagan won by a landslide. But however eager conservatives were to return to the “traditional” values of the 1950s, they could not simply undo the real changes that had taken place since then. The thriving manufacturing economy had collapsed. With it, the wages that had let millions of working men support stay-at-home wives, and keep their going-steady kids flush with spare cash for gas, milk shakes, and dances, had plummeted. So, as it happened, the Reagan Revolution did not erase the central tenets of the counterculture. Instead, it spread them.

The press loved to lampoon former radicals who switched teams during the 1980s. They could take their pick. Bobby Seale, the cofounder of the Black Panther Party who had appeared on television during the Watts riots in 1965 chanting “Burn, baby, burn,” rebranded himself as a gourmet chef. Jane Fonda went from being a protest icon to building a fitness empire based on aerobics videos.

It was not just cynicism or disillusionment that drove radicals from rioting to retail. While free-market evangelists dressed differently from free lovers, they shared certain deep similarities. The philosophies of personal freedom espoused by writers like Lawrence Lipton or activists like Timothy Leary laid the groundwork for the worldview in which, as Boesky put it, being “all right” meant being “healthy,” and being “healthy” meant “feeling good about yourself.” Where the point of living in the free world was to pursue happiness, as you defined it, without interference.

Like the Steadies who preceded them, the young people who flocked to Haight-Ashbury during the Summer of Love believed that the goal of life was well-being, and that you achieved it by consuming. The difference was that they refused to accept the limited range of goods and lifestyles on offer. They did not want to go for root beer floats with “one certain boy.” They did not want to marry the first or second girl they parked with and petted, or spend their days working nine to five to pay off the mortgage on a prefabricated house that she could grow old washing their dishes in. They wanted experience. This could mean consuming drugs or taking lovers or both.

The radicals who grew up to be yuppies added this twist. Not only should social institutions, like marriage, not stop an individual from pursuing any desire he feels; a well-functioning economy should be able to deliver any kind of love you can imagine. The core principle remained: greed was good. You are free to want what you want, whether it is a tab of LSD and an “old lady” to cook dinner for your commune in the Haight, or a Rolex and a fellow law associate to make a quick detour to pick up tuna sashimi takeout on her way home to your co-op. As the Berlin Wall fell and the Soviet Union fell apart, it seemed like the Material Girls had it right. The benefits of deregulated desire would trickle down.

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“Niche” became a business buzzword in the early 1980s. In the Era of the Steady, GM pioneered the strategy of using “dynamic obsolescence” to stimulate demand in markets that were already saturated. By introducing new models of their cars annually, and offering payment and leasing plans that made it possible to trade your older model up, car companies convinced middle-class car owners to keep shopping around for new rides, even after they had found them.

By the 1970s, however, marketers started adopting a different tactic: divide and conquer. Whether your goal was to introduce a new product, or to expand demand for something that already existed, the best strategy was to identify a narrow demographic and shape the product to appeal to it.

Some marketing experts had recognized as early as the 1950s that the economic growth based on mass consumption that took place after World War II could not last long. An article that appeared in the Journal of Marketing in 1956 proposed that the future lay elsewhere: in what the economist Wendell Smith called “market segmentation.” Soon, more and more managers were saying that it made sense to appeal to people with very different desires rather than try to capture a large swath of all consumers. By the early 1980s, technological advances made it seem as if there might in fact be no limit to how finely a good company could slice its market segments.

In 1983, an article in the academic journal Management Review predicted that the advent of computer-aided design (CAD) and manufacturing (CAM) would soon allow single companies to cater to a potentially infinite number of niches. The robots that worked in the “factory of the future” could be programmed to turn out variations on products for a fraction of what it would have cost to train and keep human workers to do the same. The rise of a single bar code system across manufacturing industries helped. Making it possible to tag and track components, along the entire supply chain, “Code 39” allowed consumers to specify what they wanted in advance. Not only could you get this year’s Buick, you could get it with whatever color, upholstery, and paneling you liked.

Meanwhile, new media technologies were making it possible to advertise to niche audiences more efficiently than ever before, too. In 1980, there were five television networks in the United States, and the big four, ABC, CBS, FOX, and NBC, commanded 90 percent of the attention of TV viewers. By 1990, there were hundreds of cable channels and none of them had anything like the market share that the big four had enjoyed. A similar sea change had taken place in radio broadcasting, and the Internet was already beginning to amplify its effects. Soon there would be more channels of communication than the advertisers of the Mad Men era could have imagined.

During this time, dating also became more targeted. Businesses aimed to attract a particular kind of dater. Like Madonna, they wanted the ones with the most cold, hard cash.

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It is not clear who coined the term “yuppie,” but credit usually goes to Bob Greene. The Chicago Tribune columnist used it in an article about the Jerry Rubin Business Networking Salon in March 1983. Rubin, the erstwhile radical who had led the Youth International Party with Abbie Hoffman and stood trial with the Chicago Eight, was now hosting weekly “networking sessions” at the legendary Studio 54 disco in New York.

“When you’re ambitious in the business world, your day does not end at 5 o’clock,” Rubin told Greene. His parties were invitation only. Guests had to pay $8 and deposit their business cards at the door, to be sorted later and ranked on a scale of networking value that ranged from A to D. The lights stayed on, and the sound track was soft classical music.

“This is not a singles bar,” Rubin emphasized. “It’s a way for businesspeople to meet other businesspeople. It’s an extension of the business day.” In March 1983, he had plans to franchise in thirty-six cities. Someone at the party that Greene attended quipped that Rubin had gone from being leader of the yippies to spokesman for the yuppies—young urban professionals. In the process, he had also converted one of America’s most famously debauched places to go out to into a place to network.

Rubin was not the only one who recognized that yuppies presented an enormous opportunity. In the early 1980s, political pollsters and market research firms became fixated on the emerging demographic. A study conducted by the California think tank SRI International in 1984 found that there were four million Americans between the ages of twenty-five and thirty-nine who earned at least $40,000 per year in professional or management positions. Between 1979 and 1983, 1.2 million of them had moved to the cities that their parents had fled for the suburbs. They bought up Victorian brownstones and co-ops in factories and warehouses, which had fallen into dereliction as America deindustrialized, and developers were now racing to renovate.

One million–plus was not enough to command serious attention from national politicians. But when pollsters lumped together all baby boomers with college degrees who were working in white-collar or technical professions, the number came to more than twenty million. As the companies aimed to capture the growing incomes of this market segment, the media obsessed about them, producing taxonomy after taxonomy of their peculiar traits.

The main mythology that grew up around yuppies concerned not how much they bought, but what they bought. Armed with credit cards, they spent high sums on things that would have seemed absurd even five years earlier. Gourmet mustard. Espresso machines. Gym memberships. They did not want it all. They wanted very specific things. To train their triceps, not their deltoids. Not a Labrador, but an Akita.

When the bestselling satire The Yuppie Handbook came out in January 1984, it established that the foremost trait of a yuppie was an obsession with particular products. The cover depicts a white couple standing side by side, with each item they are wearing and holding clearly labeled, as in a high school physiology diagram. He has a pinstripe suit, in the pocket of which there is a Cross pen; a Rolex watch; and L. L. Bean Maine Hunting Duck boots. He is carrying a Gucci briefcase and a Burberry trench coat is slung over his forearm. She sports a Ralph Lauren suit, a Cartier Tank Watch, and white running shoes. With a Coach bag on one arm, and a bag of gourmet fresh pasta on the other, she is listening to her Sony Walkman.

Name checking became a common feature of serious writing about yuppies, too. In one scene of Don DeLillo’s 1985 breakout novel, White Noise, the narrator overhears his young daughter murmuring the names of car models in her sleep. “She uttered two clearly audible words, familiar and elusive at the same time, words that seemed to have a ritual meaning, part of a verbal spell or ecstatic chant. Toyota Celica.”

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Jerry Rubin not only inspired a label for a generation obsessed with labeling. His Business Networking Salon also captured an important shift in how young professionals were approaching their careers. That was the rise of the idea that everyone should work—and should love working—nonstop. If shopgirls of the 1920s had tried to flirt, and even date, on the job, yuppies continued to hustle well after the office closed.

The complicated financial instruments and maneuvers that Wall Street bankers and their lawyers cooked up inspired many a pun. “Corporate marriage” could refer either to a corporate merger—the consolidation of companies that was generating so much of the new wealth on Wall Street—or to a romantic partnership in which both lovers were lawyers or bankers, too busy to have much sex and therefore tolerant of affairs conducted on business trips. Consider the possibilities for double entendre afforded by “horizontal mergers,” “profit squeezes,” “position limits,” “extension swaps,” “rollovers,” “interlocking directorates,” and “tender offers,” and you get a rough idea of what passed for flirtation at an MBA cocktail hour.

The famous speech that Steve Jobs gave at Stanford’s commencement in 2005 was tame by comparison. However, Jobs, too, exhorted college graduates to mix business and pleasure. Jobs insisted that the best thing that ever happened to him was being fired from his own company in 1985, because it taught him how important passion was for professional success.

“I’m convinced that the only thing that kept me going was that I loved what I did.” What he said next was widely reprinted and reblogged. “You’ve got to find what you love. And that is as true for your work as it is for your lovers … The only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it.”

Do what you love. Love what you do. By the 1990s, versions of this exhortation had become ubiquitous. Still, they could not quite cover up the fact that the career prospects of many Americans were getting worse.

In the Year of the Yuppie, the Research Institute of America found that overall, young Americans were experiencing downward mobility. Between 1979 and 1983, the median annual income for households in the twenty-five-to-thirty-four age range decreased by 14 percent in constant dollars. For the relatively unskilled, $12/hr union jobs manufacturing cars were disappearing and being replaced by $5/hr gigs flipping burgers.

Today do what you love, and you’ll never work a day in your life no longer sounds very reassuring. Since the 1970s, falling wages have meant that everyone has to work more and more, whether they love it or not.

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With the stakes of staying upper middle class so high, the yuppie who would consider dating anyone other than another yuppie would be out of his or her mind. And indeed in the 1980s, for the first time since the dawn of dating, America experienced a trend toward assortative mating.

In biology, assortative mating is “a nonrandom mating pattern in which individuals with similar genotypes and/or phenotypes mate with one another more frequently than would be expected under a random mating pattern.” Textbook example: Animals with similar body sizes tend to reproduce with each other. Although it might theoretically be possible, one rarely sees a Yorkshire terrier attempt to mount a Great Dane, or (God forbid) vice versa.

Before the rise of dating, courtship rituals like calling and church socials or Jewish settlement dances encouraged and even enforced similar mating patterns among humans. Parents and communities collaborated to ensure that young people paired off with partners who came from similar backgrounds.

Dating did not entirely break down these old biases and barriers. The middle- and upper-class men who frequented saloons and speakeasies did not all marry the Charity Girls they treated. Institutions like schools sorted young people by educational attainment, which strongly correlated with family background and future earnings. Still, the migration of courtship from the privacy of the household, or the closed ranks of community centers, into public places where daters roamed unsupervised introduced an element of unpredictability. People who went out and hit it off with a stranger might actually fall in love.

Moreover, workplaces offered opportunities for people from different classes and backgrounds to mix. At least until the early 1960s, a young woman in a professional workplace usually came from a lower socioeconomic bracket than the men she worked for. Until the 1980s, it was far from unheard of for a manager to marry a shopgirl, a boss to marry his secretary, or a doctor to marry a nurse. However, as women gained opportunities to enter corporations as associates and partners, as well as secretaries and stenographers, the office dating pool grew. It made sense that young men and women who came from similar backgrounds, had attended the same colleges and graduate schools, and spent twelve-hour-plus days working closely together would hit it off.

It is difficult to find reliable government data on how much and what kinds of people date in any given period. But it is clear that in the final decades of the twentieth century, the highly educated women climbing the corporate ladder started marrying men who were their professional peers.

A 2014 study by the National Bureau of Economic Research showed that, whereas in 1960 only 25 percent of men with university degrees married women with them, in 2005, 48 percent did. Moreover, most highly paid women loved what they did. Or at least they faced huge opportunity costs for any time they spent off the job. If and when they had children, most promptly returned to work. Amplifying the growing economic inequality among American households, assortative mating patterns reinforced themselves.

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Yuppies wanted to date other yuppies. The thing was, who had time? They may have been the first elite in human history to boast, as a mark of their status, that they could not afford a moment’s leisure. The leisure goods that yuppies did consume, they described as necessary to their work—as conveniences that made nonstop work possible (like eating out) or as part of a lifelong effort to work on themselves (like diets).

Marketers soon discovered that you could sell yuppies anything if you promised that it would make them better. In New York, in 1982, a line of fitness studios called Definitions opened, offering $600 monthly memberships to young professionals who already belonged to a gym but wanted more targeted personal training. Today you can still buy sessions with a personal trainer in packages of twenty-five, for $2,800, at any one of a dozen locations.

A sense of anxiety and precariousness lay not far below the well-toned surface of the yuppie, urging him or her to improve harder, better, faster. In 1984, Kellogg ran an ad campaign with the tagline It’s not “Are Grape Nuts good enough for you,” but “Are you good enough for Grape Nuts?” If you’re not the predator, you’re the prey, billboards for Puma sneakers warned.

No wonder people were stressed! How could you know who was good enough to date? And where could you take them out, to prove you might be worthy of them?

Yuppie daters were very particular about the restaurants they went to. Local newspapers of the 1980s are full of reviews of hot spots coming in and going out of fashion faster than the writers can keep up with. The Washington Post food editor Phyllis Richman told Newsweek in 1984 that whenever she went somewhere, “I inevitably find the same crowd of people have discovered it already.” She said that she could also sense when the yuppies would ditch a place, or taste—basically, as soon as the plebs caught on.

“When I saw white-chocolate mousse being served in a Hot Shoppe,” Richman recalled, “I knew.”

Luckily for daters who got restless so quickly, yuppies themselves came in many flavors. The press and pollsters sometimes talked about yappies (“young aspiring professionals”) and yumpies (“young, upwardly mobile professionals”). The Yuppie Handbook included a three-page spread listing the traits of Buppies (“black urban professionals”), Huppies (“Hispanic urban professionals”), Guppies (“gay urban professionals”), Juppies (“Japanese urban professionals”), and Puppies (“pregnant urban professionals”).

Each subspecies had its own defining characteristics, but all were presented as customizations you might choose on a single yuppie model. Bullet points under “Buppie” included Greater familiarity with Reggae music. Preference for custom-made business suits. Tendency to name their daughters Keesha instead of Rebecca. If female, the inclination to wear a second pair of pierced earrings with their diamond studs. Guppies, by contrast, were distinguished by summer holidays on Fire Island instead of in the Hamptons and use of free weights instead of Nautilus equipment.

These rhyming labels caught on with newspapers and magazines that carried stories about dating. The pun “yuppie love” became inescapable; “buppie” and “guppie” made good showings, too. The aural proximity of these jingling acronyms reinforced deeply held beliefs of the Reagan era: politics were passé; everyone started out the same; it was this equality of opportunity, not outcomes, that mattered.

By this logic, a yuppie might choose his mate as freely as he chose a blue or tan or silver paint job for his Saab. Indeed, satirists described yuppies as treating their love lives like any other consumer or career choice. Only, if anything, a little less important.

The section of The Yuppie Handbook devoted to dating and marriage is called “Personal Interfacing.” “Yuppies don’t love their lovers,” the preamble begins. “They love Vivaldi, their new apartments, and the color of the ocean off St. Thomas in January. They have relationships with their lovers.” According to the Handbook, yuppies broke relationships, like business deals, into three stages: (1) getting into, (2) working on, and (3) getting out.

In an article on “Yuppie Love” in its 1984 Year of the Yuppie issue, Newsweek adopted a similarly arch tone. “It can happen anywhere, anytime. You’re sitting at a sales meeting, and this fabulous looking guy stands up and gives this really tremendous presentation, and all of a sudden you know, you’ve just got to have him in your division.”

All joking aside, many yuppie daters felt despair. In 1985, the Associated Press interviewed a Boston social worker who taught a free course on “Spouse Hunting” at the city’s Adult Education Center. She recalled that ten years earlier, most of her students had found being single glamorous. Now, they all seemed miserable. “Urban life is so anonymous,” she said, “everyone is dying to know how to meet somebody.”

Spending long days at the office, and one or two hours a day besides in the gym and personal-training sessions, many yuppies found that they had little of themselves left over to invest in romance.

What could you do if doing what you loved took so much time and energy that you had none left for dating? One 1980s dating advice manual suggested buying an eye-catching breed of dog to meet other singles. The fitness addict could kill two birds with one stone by taking his or her canine conversation piece for a jog.

“That’s still a thing!” my friend exclaims when I read this tip aloud to him.

A more efficient approach was figuring out what you wanted in a partner before you started shopping. Just as businesses developed to cater to yuppies who were too busy to cook, or wanted to target their trapezius muscles without wasting time on, say, rowing, so did new services promise to help you date. To have highly specific taste was a plus: It helped you speed up your search by narrowing it down.

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Cookie Silver was short. But she wanted tall.

“I want tall,” she kept telling her matchmaker. “When I’m with a short man we look like Munchkins.”

“But this one’s a doctor,” the matchmaker protested, of one of her prospects. “When he stands on his wallet, he’s over six feet!”

Cookie recounted her story to the Chicago Tribune in 1985. By then, she and the tall man she held out for—an entrepreneur by the name of Howard Feldstein—had met, married, and acquired the local franchise of the video-dating service that introduced them. IntroLens was growing at a quick clip, adding hundreds of users every month and opening several new offices across the Midwest. It was only one of a spate of new businesses offering dating services to yuppie lonelyhearts. These promised to help daters find what they wanted in what little time they had.

Dating services had been around since the 1960s. The first primitive forms of computer dating debuted during that decade. Like Facebook, Operation Match was designed by three students at Harvard. It allowed curious singles to submit several pieces of information about themselves and what they wanted, have these cross-referenced in a database, and receive a handful of recommended partners.

In 1964, an accountant and an IBM programmer in New York unveiled a similar prototype that they called Project TACT (for “Technical Automated Compatibility Testing”). It catered to singles on New York’s Upper East Side. But these were novelties. The first “introduction services” to develop viable business models were low-tech.

You would sign up, usually after a phone call, and then make an appointment to do an in-person interview with one of the “counselors” who worked in the office. The counselor would ask you a long list of personal questions—about your childhood, romantic history, job, hobbies, and religious preferences—and then whether you yourself had any deal breakers. Would you date a smoker? Would you date a divorcé? Within a few weeks you would start receiving cards in the mail with the names and phone numbers of dating prospects. These would continue arriving as long as you paid your membership fee. If you liked someone after talking on the phone, you could meet in person. The whole thing was basically like outsourcing the role of a meddlesome aunt who sets you up on blind dates to a stranger who had a bigger Rolodex.

The personals sections that proliferated in the backs of many newspapers and magazines in the 1970s seemed less enticing to yuppie daters of the 1980s. Dating services that required so little investment up front were generally suspected of delivering low returns. For singles who wanted more selectivity, video dating offered an alternative.

The first video-dating services started appearing in the 1970s, as the prices of video cameras, cassettes, and players fell. At most companies, when you signed up, you would be paired with a counselor. After you filled out some of the usual questionnaires—with basics like race, age, education level, occupation, and religious beliefs—the counselor interviewed you on camera, hiding herself offscreen. At IntroLens, Cookie Silver called this part “the talk show.” When you had finished, she allowed you to view your tape. You could ask to reshoot and edit, if you wanted. She labeled the finished product with your first name and filed it in a video library. At the best companies, these libraries were large.

After you had made your recording, your matchmaker ran the answers you had put on your questionnaire through a computer database, which generated a list of prospective matches for you. You could make an appointment to pull the videos these singles had made, so that you could screen them in a private room. If you liked what you saw, you told the service; the service contacted the person on the tape and offered to show him your video. If you both were interested, you would be introduced. At most companies, these services would run you between $500 and $1,000 per year. Some also offered more expensive “lifetime” memberships, which were valid as long as you remained unmarried.

The first video-dating company in the United States, Great Expectations, was founded in Los Angeles in 1975 by a mother and son team, Estelle and Jeff Ullman. It expanded quickly, franchising all over California and the West; in 1990, Jeff claimed that Great Expectations was responsible for six thousand marriages. (A current Facebook page for couples who met through the service fondly remembers Estelle as “everyone’s Jewish mother.”) In the meantime, the company had inspired a lot of copycats. The first IntroLens office opened in 1979. Between 1980 and 1983, similar services rapidly started multiplying in cities across America.

Eventually, video-dating services would cater to daters at almost every price point and in every demographic. There was Soul Mates Unlimited (for Jews in California) and Soul Date a Mate (for African Americans in or around Framingham, Massachusetts). In Boston there was Partners (for gays and lesbians) and Mazel Dating (for Jewish singles). Washington, D.C., had Today For Singles Inc., which served daters with herpes.

In 1988, an exhibition at the Chicago Zoo called ZooArk even let visitors play a video-dating game on behalf of animals that belonged to endangered species. Using a computer connected to the International Species Information System—the resource that professional zookeepers use to do this—the exhibit let visitors browse prospective mates for one of the zoo’s “bachelors” and two “bachelorettes.” These were a white, black, and Asian rhinoceros.

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In personal ads, computer databases, and video-dating tapes of the 1980s we can see contemporary online dating technologies struggling to emerge from their analog chrysalis. If yuppies had not invented the Internet, their personal assistants would have had to invent it for them. These text and VHS predecessors of online dating prepared us. For one thing, they taught busy singles to focus their romantic expectations—to spell out what they had to offer, what they were looking for, and where they might be likely to find it.

Print classified ads already required daters to do this. They forced you to boil down yourself and your desires into sound bites—and to know your audience. You could expect different people to read the personals at the backs of The New York Review of Books versus New York magazine, in the African American paper the Los Angeles Sentinel versus the beefcake glossy Exercise for Men Only. You had only a few words to catch the right eyes. Jeff Ullman, the Great Expectations founder, traveled the United States offering motivational lectures and seminars to anxious singles. When I reach him at his home in Colorado, he recounts how he used to boost the confidence of attendees by telling them they should not feel ashamed to be selling themselves.

“‘What is advertising?’ I would ask. ‘Let’s look it up in the dictionary.’” Then he would pull out a dictionary.

“‘Advertising. Taking a product or a service and promoting it.’ I believe that is what you’re doing. You’re a product, you’re a service, you’re a thing—you’re a bag of carbon and water—and you’re here because you want to mate, date, procreate. Every one of you is advertising for yourself.”

As more and more dating services began using computers—creating databases of clients and cross-listing them—the imperative to go niche would turn from being a good strategy to a technical requirement. You had to be able to express your personality in exactly the right keystrokes. Daters quickly learned to convert themselves to code.

Until the early 1980s, dating services had been seen as slightly pathetic. You can tell by how adamantly the pioneers of video dating insisted that their customers were not pathetic. Jeff Ullman, the Great Expectations owner, actually sued a local bank in Southern California whose billboards joked that its generous interest rates offered clients “more zeros than a dating service.” “When I saw it,” Ullman fumed to the Los Angeles Times, “I almost drove off the road!”

“These aren’t losers, you understand,” Joan Hendrickson assured The Washington Post of the clients she served at the branches of her upscale D.C. service, Georgetown Connection. “On the contrary, these are people who are confident and willing to take a risk.” In a business piece on the spectacular growth of the People Network and several other New England video-dating companies between 1981 and 1983, The Boston Globe concurred. “Once viewed as the alternative for love’s losers, they appear to be gaining a new image of respectability, especially among singles who are busy career professionals.

Yuppies had made work itself glamorous. In doing so, they had made it admirable (rather than pitiful) to be too busy to have a social or romantic life.

The way people talked about video dating reflected a new level of comfort with the idea that courtship was simply another part of the economy. Today, controversial dating services frequently invoke the existence of demand for their services as a moral justification that needs no further explanation. Before the August 2015 data breach that made Ashley Madison, the dating site for cheating spouses, infamous, the founder, Noel Biderman, defended it by saying that it simply facilitated interactions that would take place anyway. SeekingArrangement describes the “sugar dating” it brokers as “relationships on your terms.” It promises convenience—“find a relationship anywhere, anytime on any device”—and advertises “ideal relationships” that are “upfront and honest arrangements with someone who will cater to your needs.”

Of course, the market does not always offer happiness. The idea that new technologies could create a perfect delivery system for human desire set many daters up for disappointment. For some, it inspired unrealistic expectations.

In a video-dating tape that is still floating around on YouTube, a thin man with a mullet describes what he is hoping for: “a figure that is sexy … slim, tight, excellent legs.” He pauses to look up into the camera and literally smacks his lips. “Mmmm.” His was the problem that still confronts daters on many apps and services: The specter of infinite possibility and choice creates hopes that only can be dashed, again and again, in a search that never ends.

Article after article related how brutal video dating was on women. A headline in the Chicago Tribune joked drily that “For a 4-Figure Fee, You Get Rejected Regularly.” The story focused on the plight of an attractive, professional forty-something-year-old woman, recently divorced, who was roped into paying $1,450 for a membership from which she never got one single date. “Video dating services are great,” the authors joked. “Just as long as you’re either (a) A gorgeous woman, under 35, with a glamorous career, or (b) An average-looking man, under 65, with an ordinary job.”

Even the proprietors of dating services admitted that it was hard for them to help female clients who had passed middle age. Bob Greene, the columnist who had coined “yuppie,” told the heartbreaking story of a seventy-year-old widow named Nancy who drove in from the Chicago suburb of Berwyn to sign up for a service called Sneak Previews Inc.

“My husband died seven years ago,” Nancy told the owner, Joseph De Bartolo. “You get so lonely when that happens. Every year you get lonelier.”

De Bartolo told Greene that he had not wanted to take her money. He warned the septuagenarian, “We really don’t have a lot of people who it might be appropriate for you to choose.”

“That’s okay,” she replied. “I don’t expect to walk out with a date today.” When Greene followed up several months later, he found Nancy at home, alone.

*   *   *

Like the bars, speakeasies, and school dances that came before them, computer-dating services were platforms. Only the technology of courtship was supposed to have improved. Computers promised to rationalize the dating market—to clear up inefficiencies that kept the supply of yuppie singles from finding its demand. When online-dating companies began to take off in the mid-1990s, they assembled larger and larger databases and deployed automated processing power. As more Americans got online, and it became possible to delegate the work of a Cookie Silver to algorithms and a webcam, dating services would become affordable and available to virtually anyone who wanted to use them. You could belong to two or three dating services at once. By the turn of the millennium, the numbers of members of sites like Match.com and PlentyOfFish had climbed into the tens of millions.

In an article that appeared in Wired magazine in 2002, Nerve.com’s founder Rufus Griscom declared that the ascendancy of online dating was inevitable.

“Twenty years from now, the idea that someone looking for love won’t look for it online will be silly, akin to skipping the card catalog to instead wander the stacks because ‘the right books are found only by accident,’” Griscom wrote. “We have a collective investment in the idea that love is a chance event, and often it is. But serendipity is the hallmark of inefficient markets, and the marketplace of love, like it or not, is becoming more and more efficient.”

Had we come Back to the Future? At the dawn of dating, all sorts of people had decried the fact that courtship was moving out of the home and into an anonymous, public world where money changed hands. Policemen worried that making dates was equivalent to turning tricks. Love was supposed to lie outside the economy; women could only give it away. By the 1980s and ’90s, however, respectable people were celebrating the possibility that courtship might be made to behave as rationally as the market was supposed to, via technologies that let you “do comparison shopping of potential dates from the comfort and privacy of your own home.”

*   *   *

The undercover vice investigators who stalked Charity Girls in the 1900s and 1910s were horrified by their transactional approach to romance. However, an odd couple that appears all over Hollywood comedies of the 1980s suggests that by then, mass audiences embraced it. The couple consisted of a prostitute and an entrepreneur.

It started with Risky Business (1983).

In Risky Business, when his wealthy parents leave him alone for a weekend, the high school senior played by Tom Cruise phones a call girl, Lana, on a dare. After their night together leaves him in her debt, and her pimp steals his parents’ chichi furniture, Tom Cruise must go into business with Lana to earn the money he needs to buy his heirlooms back. They team up to run a prostitution ring out of his family home for one night.

“My name is Joel Goodson,” Cruise announces after it has all worked out. “I deal in human fulfillment. I grossed over eight thousand dollars in one night.” Today, the portrait of the entrepreneur as a young pimp—or, rather, teen male madam—feels prescient. Had Joel Goodson been born two decades later, he might have founded Facebook. Like Mark Zuckerberg, he uses his parents’ capital to create a platform where others can exchange attention and emotions so that he can skim off the surplus.

In the Calling Era, the parlor, watched over by the lady of the house, was the inner sanctum of a female world entrusted with taming male tendencies toward aggression, greed, and lust. By the time of Risky Business, the parlor had become a living room and then a pop-up brothel. No parents were home.

The mythology of the 1980s and early ’90s glorified the escort and the entrepreneur as a perfect match because neither had anything he or she would not be willing to sell. In Pretty Woman, Richard Gere puts this bluntly. “You and I are such similar creatures,” his suave businessman tells the streetwalker played by Julia Roberts. “We both screw people for money.”

There was a lot embedded in this crude pun. For one, the idea that at the bottom, the escort and the entrepreneur did the same kind of work. In the late 1970s, the United States continued to deindustrialize, and the country experienced a trade deficit. Unable to keep up with increased competition from Japan and Germany or to afford the increasingly expensive oil that had once powered industrial production, the United States grew its service sector. Both the streetwalker and the stockbroker belonged to it.

In this sense, Richard Gere was right: They were not so different. Yet this service sector itself continued to split into two increasingly unequal groups. On the one side was the precarious and poorly paid majority; on the other were finance aristocrats. The kind of work the first did tended to be thought of as female—cleaning, serving food, handling customers, and so on. The kind the second did was quantitative and competitive; in their broad-shouldered suits, its icons projected masculinity. So while they had their similarities, these lovers were also opposites. They both screwed people. But they had very different power relationships with them and received different rewards.

Pretty Woman became the highest-grossing love story of this era, because it turned the disappearance of the American middle class into a fairy tale.

Many other romantic comedies told tales of class mobility, where humble, honorable people manage to marry out of dead-end positions into yuppiedom. The 1988 classic Working Girl, for instance. The title wink-winks, yet again, at the fundamental similarity of the businessperson and the sex worker. In the beginning, the “working girl” secretary played by Melanie Griffith must commute from Staten Island to work in a Wall Street office as a personal assistant to the pantsuited megabitch played by Sigourney Weaver. However, when an improbable series of events lead Melanie to impersonate her boss, she ends up landing a big deal. She also manages to steal her boss’s fiancé, Harrison Ford.

The final scene shows what happily ever after in a yuppie household looks like. Getting ready to leave for work in the morning, Melanie and Harrison wolf down their low-cal breakfast in a wordless ballet. As she pours his coffee, he pops the toast out of the gleaming toaster, and sticks it in her open mouth.

*   *   *

Calling and old-fashioned courtship, the scenery and setting of the parlor, encouraged the fiction that love had nothing to do with the economy. For bourgeois people, marriage was supposed to be a matter of spontaneous, spiritual affinity; for others, it was supposed to propagate a community or bloodline. But as dating neared its centennial, the situation reversed. Dating came to be seen as just another kind of transaction. Many people struggled to reconcile their desire to live efficiently with their desire to feel sexual desire itself.

Shortly after the 1987 stock market crash, Newsweek reported that a new disorder was troubling the yuppie population. “Psychiatrists and psychologists say they are seeing a growing proportion of patients … whose main response to the sexual revolution has been some equivalent of ‘Not tonight, dear.’” The Viennese psychiatrist Helen Singer Kaplan, who had established the first academically accredited sex therapy institute in the United States, in New York in the 1970s, diagnosed this. She called the problem “inhibited sexual desire” (ISD). It entered the DSM-III in 1988.

“Over the past decade ISD has emerged as the most common of all sexual complaints. By varying estimates, anywhere from 20 to 50 percent of the general population may experience it at some time, to some degree,” Newsweek reported. “One clinician goes so far as to call it ‘the plague of the ’80s.’” Against this backdrop, the sex worker starts to look like the prototype for a new woman who is expert in managing feelings—inspiring particular feelings in others and repressing her own—until the time when revealing them might be advantageous. This expertise allowed her to convert the desires of others into money, which was what any yuppie lover most wanted. She made feelings economically productive.

In Pretty Woman, Julia Roberts lands Richard Gere by doing precisely this. Richard Gere admits to being a commitmentphobe who has never felt capable of falling in love; friends Julia Roberts meets when he takes her to a horse race emphasize that he is universally desired. No one seems struck by the fact that his professed inability to have feelings qualifies him as a textbook sociopath.

Richard Gere is handsome and eligible, and Julia seduces him by masterfully turning her own body into a commodity. “Did I mention, my leg is 44 inches from hip to toe?” she asks, in an early scene when she embraces him in the bathtub in his swank suite at the Beverly Wilshire Hotel. “So basically we are talking about 88 inches of therapy, wrapped around you for the bargain price of $3,000.”

When Richard returns a necklace that he had borrowed for her to wear to the opera, after failing to man up and become her boyfriend, the jeweler sighs. “It must be hard,” he says, as he accepts it back, “to give up something so beautiful.”

It is these words equating Julia Roberts with the necklace that make Richard realize that he has made a terrible mistake. He sprints away to get her back, scrambling up her fire escape just in time for the happy ending.

Bret Easton Ellis’s novel American Psycho came out several months after Pretty Woman. Whereas Pretty Woman was instantly beloved, American Psycho was and remains highly controversial. Several publishers dropped the manuscript before Vintage finally published it. But American Psycho basically tells the same story as Pretty Woman in another genre: horror.

Like Richard Gere, the protagonist Patrick Bateman is a wildly successful, handsome finance guy with a good pedigree who cannot feel anything without engaging the services of sex workers. Richard Gere consumes Julia Roberts figuratively. By letting him treat her body like a beautiful object, she helps him find it in himself to feel love. Patrick Bateman literally murders and eats the prostitutes he sleeps with.

“When I see a pretty girl walking down the street,” he jokes to a colleague, “I think two things. One part wants me to take her out and talk to her and be real nice and sweet and treat her right.”

“What does the other part of him think?” the colleague asks.

“What her head would look like on a stick.”

Over the course of the novel, Bateman gnaws girls’ pussies off with his teeth and rips their limbs apart. He stuffs their orifices with Brie and prods a pet rat to eat their bodies from the inside out. He tries to cook girls into sausages and meat loaf. He fails. The matronly apron he wears is a joke. He is no good at cooking; he has clearly never had to do any housework for himself.

Bret Easton Ellis leaves his narrator unreliable. But the fact that we cannot be quite sure whether Patrick Bateman really kills anyone or is just hallucinating the whole thing should not reassure us for a minute. It is just another symptom of a terrifying kind of feelinglessness, the total devaluation of emotion in his world.

American Psycho highlighted the dark underside of a dating market that said that anything anyone wanted and could pay for was fair game. It exposed the yuppie as more than dysfunctional. He was satanic.

*   *   *

Meanwhile, downtown, a real-life nightmare was unfolding.