Is dating worth the effort?
An illustration of an iPhone beaming pink cartoon hearts towards someone
Dating “often feels like the worst, most precarious form of contemporary labor: an unpaid internship,” Moira Weigel writes.Illustration by Alain Pilon

As we learn from the podcast “Reply All,” which reported the tale, Suzanne was not the only woman on whom John had chosen to bestow his favor. Six months into their relationship, she discovered that he was seeing half a dozen other women, one of whom he’d been stringing along for two years. All of them had received the couch-spooning treatment. John was a champion girlfriend accumulator, the ringmaster of a romantic circus that only he could see. Every so often, one of his paramours would catch on and alert the others. Then he’d block them all on social media and begin the whole thing again.

In one sense, this is a story about the exploitative possibilities of online matchmaking: the opportunities to flagrantly misrepresent oneself, the ease of trawling for specific targets. (John, who was white, pursued only Asian women, leaving his girlfriends with the icky sense that they’d been fetishized as well as deceived.) Still, romantic scammers aren’t an invention of modern courtship and its digital devices. They’re a staple of Jane Austen novels: John Willoughby, who caddishly breaks Marianne’s heart in “Sense and Sensibility”; George Wickham, who reels in both Lizzy and Lydia Bennett in “Pride and Prejudice”; Frank Churchill, in “Emma,” who flirts with Miss Woodhouse while being secretly engaged to her frenemy, Jane Fairfax. John, though, was a stranger breed of seducer. As a twenty-first-century guy living in one of the most culturally liberal of American cities, he had options available to him that men in Regency England did not. He could have chosen to be a player, sleeping around with abandon, or the kind of cheater who supplements monogamy with a series of flings. He might have practiced polyamory, consensual open love. But John, with his flair for saccharine cuteness and his insistence on treating his conquests like romantic-comedy heroines, didn’t like just to play or cheat, and he certainly didn’t like any of his girlfriends to suspect that they didn’t have his full attention. What he liked to do was date.

According to Moira Weigel, the author of “Labor of Love: The Invention of Dating” (Farrar, Straus & Giroux), most people are not like John in this respect. However much you might enjoy going out to dinner or stumbling home with someone new, you date in the hope that the day will come when you’ll never have to date again. “If marriage is the long-term contract that many daters still hope to land, dating itself often feels like the worst, most precarious form of contemporary labor: an unpaid internship,” Weigel writes at the start of her book. The process of testing out potential mates, and of being tested by them in turn, can be gruelling, bewildering, humiliating. Using another metaphor, Weigel compares the experience to being cast in a bad piece of experimental theatre: “You and a partner showed up every night with different, conflicting scripts. You did your best.” This makes dating sound a lot like a recurring anxiety dream. You’d have to be a masochist not to try to wake yourself up.

Weigel, who is in her early thirties, is a Ph.D. candidate in comparative literature, film, and media at Yale; “Labor of Love,” a perceptive and wide-ranging investigation into the history of dating in America, is her first book, sprouted from the seed of unpleasant personal experience. At twenty-six, she was involved with an older man who was torn between her and an ex he hadn’t lost interest in. Maybe he wouldn’t choose either of them; he told Weigel that he found the whole premise of long-term romance “ideologically suspect.”

She realized that she had no idea what she herself wanted from romance. Her Irish Catholic mother and the self-help industry told her that the goal should be marriage, and soon. She asked her sort-of boyfriend for his opinion. He thought that everyone should want to pursue happiness. Weigel had a revelation: she was always turning to a man to tell her what she was after, and the institution of dating was to blame. It trained women “in how to be if we wanted to be wanted.”

Hence “Labor of Love,” an exploration of that training, in which Weigel reaches two main conclusions. The first is that though dating is passed off as a leisure activity, it really is a lot of work, particularly for women. It requires physical effort—all that primping, exercising, shopping, and grooming—as well as sizable investments of time, money, and emotion. In our consumer society, love is perpetually for sale; dating is what it takes to close the deal.

Her second conclusion is that the way we consume love changes to reflect the economy of the times. The monogamy of the booming postwar fifties offered “a kind of romantic full employment,” while the free love of the sixties signified not the death of dating but its deregulation on the free market. The luxury- and self-obsessed yuppies of the “greed is good” eighties demanded that the romantic market deliver partners tailored to their niche specifications, developing early versions of the kinds of matchmaking services that have been perfected in today’s digital gig economy, where the personal is professional, and everyone self-brands accordingly.

Dating is therefore a powerful force of social control—but what do we actually mean by “dating”? Weigel begins her survey at the turn of the twentieth century, when single women were increasingly leaving the towns and farms where they’d been brought up and flocking to industrializing cities to work in factories, laundries, and department stores, their ranks swelled by the arrival of immigrants. Domestic privacy was hard to come by. Working women bunked in tenements with relatives or streamed into boarding houses with rules against male visitors. So they went out, to parks and dance halls, saloons and restaurants, nickelodeons and penny arcades—to the streets themselves, teeming centers of working-class social life—where they could have a good time and meet men on their own.

There were a lot of men to meet. The term “date” originated as slang referring to a woman’s date book, and showed up in print in 1896, in “Stories of the Streets and Town,” a Chicago Record column that offered middle-class readers a taste of working-class life. Artie, a young clerk, confronts a girlfriend who’s been giving him the slip: “I s’pose the other boy’s fillin’ all my dates?” He wasn’t always so begrudging. A later column reports Artie’s admiring observation that a certain girl’s date book was so full she had to keep it “on the Double Entry System.”

Not surprisingly, these new female freedoms came with a catch. The pursuit of leisure cost more than most single working-class women (paid a fraction of what men were) could readily afford. Weigel quotes a 1915 report by a New York social worker: “The acceptance on the part of the girl of almost any invitation needs little explanation, when one realizes that she often goes pleasureless unless she accepts ‘free treats.’ ” To have fun, a woman had to let a man pay for her and suffer the resultant damage to her reputation. Daters were “Charity Girls”—“Charity Cunts,” in a dictionary of sexual terms published in 1916—so called because they gave themselves away for free.

Dating thus amounted to a double bind. If women went out, they were seen as akin to whores, who at least got cash for their trouble—a distinction that was lost on the police, who regularly arrested female daters for prostitution. On the other hand, if women stayed in they couldn’t bump into eligible bachelors. In “All the Single Ladies: Unmarried Women and the Rise of an Independent Nation” (Simon & Schuster), the journalist Rebecca Traister describes the attempts of one establishment, the Trowmart Inn, in Greenwich Village, to address this problem. Unlike most boarding houses for working women, the Trowmart didn’t impose a curfew, and actively encouraged male visitors. The Times reported that its founder wanted to give women of “the class which labors for a small wage” a place where they could be courted with the kind of decorousness that the dating scene lacked: “Girls of gentleness and refinement do not care to be courted upon the open highway, nor in public parks, and thus the world is filling with spinsters who . . . had they a proper place in which to entertain their admirers, would develop into happy, excellent wives and still happier mothers.”

What the Trowmart founder had in mind was “calling,” the respectable mode of courtship that had been practiced during the nineteenth century and into the twentieth by the aspirational middle class. After a girl came out into society, around the age of sixteen, her guardian would invite young men to call on her at home. They would chat; she might play something on the piano. In subsequent “seasons,” girls were permitted to extend invitations themselves. Calling had rules, which were publicized by women’s magazines like Harpers Bazaar and Ladies’ Home Journal. A man should call within a fortnight of receiving an invitation. A girl’s mother must chaperone the first visit but eventually leave the couple alone. A young lady should never walk her guest to the front door.

Compared with dating, calling sounds unbearably repressive. Weigel points out that it turned women, primly cloistered in their drawing rooms, into passive objects of male desire. (In “The Glass Menagerie,” Amanda Wingfield, with her fantasy of a “gentleman caller,” suggests the more destructive effects of this philosophy.) And the rules were firm. In 1907, Ladies’ Home Journal instructed women never to go to a restaurant in the company of a man. Think of the opening scene of Edith Wharton’s “The House of Mirth,” published in 1905 and set a decade earlier, in which Lily Bart, a single woman struggling to keep her place among New York’s élite, agrees to take tea at the apartment of the lawyer Lawrence Selden, a single man. You don’t have to read any further to know that the novel will end in her ruin.

But calling gave women certain advantages. As the historian Beth L. Bailey argued in a 1988 book on courtship in twentieth-century America, calling, which took place in the female “sphere” of the home, afforded women a degree of control that dating in the public, male sphere didn’t. Plus, it was up to women to pursue men. Bailey quotes a young man’s letter that was published in Ladies’ Home Journal in 1909: “May I call upon a young woman whom I greatly admire, although she had not given me permission?” Not if he wanted to have a chance with her, came the reply. Compare this, as Bailey does, with the warning issued in a dating guide from the nineteen-fifties—representative of a genre that has survived with roachlike endurance to the present day—that for girls to ask guys out would be “to usurp the right of boys to choose their own dates,” a custom that the guide claimed stretched back to the Stone Age, when, readers were blithely informed, men regarded women as prey and took them by force.

The shift from calling to dating happened quickly, in the way that such shifts often do. The rich copied the poor; the middle class copied the rich. In 1914, Ladies’ Home Journal reported that it was now “considered ‘smart’ to go to the low order of dance halls, and not only be a looker-on, but also to dance among all sorts and conditions of men and women.” The sense of social liberation was hardly shared by all. Weigel notes the Harlem Renaissance writer Wallace Thurman’s observation, in the mid-nineteen-twenties, that his neighborhood’s night clubs had become de-facto segregated “shrines” to which self-styled white sophisticates made pilgrimage on their nights out. The upper crust flocked, too, to drag shows and gay burlesques, part of a long tradition of straight daters cribbing from gay life. (Just as, in more recent history, Tinder launched on the heels of Grindr, so were the straight singles bars of the sixties inspired by gay nightspots. One of the most popular of these franchises still thrives, albeit in much altered form, under its original name: T.G.I. Friday’s.)

Soon enough, dating became an activity by which women tried to transcend class. By the nineteen-tens and twenties, as it became commonplace for women to work in public as shopgirls, laundresses, and waitresses, the hope of “dating up” by snagging middle-class customers to go out with, and, eventually, marry, became a trope—one that largely excluded working-class black women, the majority of whom were restricted to jobs as maids.

“Do you know why we pulled you over today, sir?”

To sell themselves as romantic prospects along with whatever else they were selling, girls cultivated a certain look—makeup, recently the province of actresses and prostitutes, went mainstream—and a certain style: solicitous, flirtatious, credulous, coy. Fast-forward a few decades and you get Helen Gurley Brown, self-appointed patron saint to single girls, impressing upon female office workers the importance of not leaving “any facet of you unpolished,” lest an eligible colleague who glances your way fails to keep glancing.

Dating, born in cities, grew up on the college campus. In the twenties and thirties, privileged College Men and Coeds pursued one another with a libidinous vigor to rival latter-day “hook-up culture.” Students got physical both at official mixers and at gatherings of their own—“mothers complain that modern girls ‘vamp’ their sons at petting parties,” reads a 1922 Times headline dug up by Weigel. They escaped adult scrutiny via that supreme agent of American sexual freedom, the automobile. They danced dirty. And they drank—a lot. “Hold me up, kid; I’m ginned,” a girl at a social slurs to a fraternity brother in the 1924 campus novel “The Plastic Age.” Looking around for backup, he sees that just about everyone else is either crying or vomiting in the bushes.

The point of all this canoodling wasn’t to get married. No woman expected to traipse down the aisle with her dance partner from last Saturday night, regardless of what they had done in the dark. The point, Weigel notes, was to compete. Students “rated” one another’s social credit; the better you rated, the more you dated, and the more you dated, the higher you rated. None other than the anthropologist Margaret Mead characterized college dating as “a competitive game” rather than a proper courtship ritual. Students weren’t playing for emotional keeps. The stakes were the admiration and envy of one’s peers.

This state of affairs changed during and after the Second World War, at least in part as a matter of wartime necessity. With so many men away, Weigel explains, girls had to hang on to the boys they could get. During the years of postwar abundance, dating became a crucial feature of the American consumer economy, something that teens of the rapidly expanding middle class, newly awash in disposable income and unencumbered by dark memories of the Depression, could spend their dollars on. Everybody was doing it, and so, for once, romantic supply equalled demand: people paired off.

You’d think that adults would have cheered their offsprings’ coupling tendencies. “One boy to laugh with, to joke with, have Coke with,” sings Kim MacAfee, the fifteen-year-old heroine of “Bye Bye Birdie,” expressing the fantasies of her generation: “One boy, not two or three.” Having a Coke with a single beau seems a lot more wholesome than attending a petting party with a bunch of them.

But grownups didn’t cheer. Advice columns lamented the “ridiculous custom” of teen-age couples “pairing off to the exclusion of everyone else on the dance floor.” The Baltimore Afro-American, one of the country’s biggest black-owned papers, told its younger readers that trying out multiple romantic partners was healthier, in the long run, than “settling down” too fast. Young people were encouraged, in fittingly consumerist terms, to “shop around,” so that they wouldn’t find themselves saddled with a lacklustre steady for life. Playing at marriage, they were told, would leave them with all the institution’s ills and none of its benefits. This was objectively true in one respect at least: teen-pregnancy rates soared, both in and out of wedlock. Trying to stay one step ahead, Catholic schools across the country started expelling students found to be in monogamous relationships.

On the plus side, Weigel argues, the culture of going steady allowed couples a degree of emotional intimacy that earlier dating models lacked. But its restrictive mores also put the onus on girls to regulate both their own sexual urges and those of their boyfriends. The result “was a setup that subjected girls to constant stress, self-blame, and regret.” Weigel describes an illustrative scene from a forties teen novel in which a group of boys—“The Checkers,” they’re ominously called—hang out in front of a favorite date spot in their Wisconsin town in order to report, the narrator says, “any violations on the part of the girls who are supposed to be going steady.”

The history of dating, then, is also the history of the surveillance of daters. As young people figured out how to conduct their private lives away from the supervision of parents, teachers, and chaperones, they took it upon themselves to do the supervising, creating and enforcing their own codes of behavior. They proved to be remarkably adept at it. No one, it turned out, regulates the sexual and romantic lives of young people as effectively as young people themselves.

That’s one conclusion to draw from “American Girls: Social Media and the Secret Lives of Teenagers” (Knopf), by the Vanity Fair reporter Nancy Jo Sales. Even if you’ve been following teen social-media horror stories—the recent case of an Ohio girl live-streaming her friend’s rape comes to mind—Sales’s book makes for an urgent, dispiriting portrait. Teen-age girls are the largest group of social-media users in the country. “For the first time,” Sales writes, “most American girls are engaged in the same activity most of the time.” Curious to see what effects such constant digital engagement were having on teen-age girls, she interviewed a diverse group of more than two hundred of them.

Sales learned that girls are being bombarded on their phones with images, videos, comments, and the like that “are offensive and potentially damaging to their well-being and sense of self-esteem.” She writes about an American Psychological Association report published in 2007, just before the iPhone launched, which found that girls were “treated as ‘objects of sexual desire . . . as things rather than as people with legitimate sexual feelings of their own’—in virtually every form of media, including movies, television, music videos and lyrics, video games and the Internet, advertising, cartoons, clothing, and toys.” The report saw links between such sexualization and mental-health problems, including anxiety, depression, and eating disorders. Sales argues that sexualization has become “a prevailing mode, influencing how girls see themselves, as well as how they present themselves.”

Sales begins her book with the story of Sophia, a thirteen-year-old in Montclair, New Jersey, who receives a text one day after school from Zack, a boy in her eighth-grade class: “send noodz.” (Sales has changed her subjects’ names.) Girls are often solicited for naked pictures, and, as Sophia knows, it isn’t uncommon for the photos to be compiled and shared on virtual “slut pages.” Still, it hasn’t happened to her before: “ ‘I was like, Whoa, he finds me attractive?’ ” Sophia hasn’t yet had her first kiss; she wonders if it might be with Zack. Actually, Zack confesses, he just needs the photo so that he can trade it to a high-school senior in exchange for booze. “Lol,” Sophia responds. There’s a consensus among her friends that humor is the de-rigueur response, a way to demonstrate “chill”—detachment, a feigned attitude of control in situations designed to wrest it from them.

One way to get back at the boys is by posting selfies, a declaration, at least in theory, that girls have the right to present themselves however they want. Sophia has an Instagram account full of selfies, all capturing the same pose—“bite-tongue smile”—which she laughingly calls “my brand.” (It’s a knockoff; here, as throughout the book, Sales spies the long shadow cast by the likes of Miley Cyrus and the Kardashians.) She and her friends use apps to edit their pictures, and, like a pop star dropping an album, post them when they think most people will see them. Sometimes, Sophia tells Sales, it takes up to seventy tries to get the shot right. Then she monitors the comments and the likes as they come in. “I feel like I’m brainwashed into wanting likes,” Sophia says.

Weigel would point out that girls like Sophia are expending an enormous amount of labor to compete in the online sexual marketplace run by their peers. And boys are hardly the only ones who dictate the terms. “It’s like you spend half your time managing your reputation,” another one of Sales’s subjects says, referring to the effort it takes to keep up the requisite stream of flattering commentary on other girls’ Instagram selfies. Sierra, a fifteen-year-old from Jamestown, Virginia, who is frequently cyberbullied, monitors her Facebook, Twitter, Instagram, and Ask.fm accounts as she speaks with Sales, deleting negative comments the moment they appear. It’s “a lot of work,” serving as her own censor, Sierra admits. Another girl tells Sales that social media is “destroying our lives.” Sales asks why she doesn’t quit. “Because then we would have no life,” she is told.

Like many adults trying to understand a younger generation’s approach to sex and romance, Sales—who has a teen-age daughter herself—is curious to hear girls’ thoughts on dating. “Dating is just for other people to know that you’re dating,” Sophia says. “People post about it all the time. Like kissing photos.” This seems to be the consensus across “American Girls.” It sounds familiar. “Men were only the gloves with which one slapped the face of girls,” says a character from a nineteen-twenties short story about college which Weigel quotes. “It was women one dueled.”

When it comes to teen-agers and college students, the notion of “dating” is often presented in opposition to casual sex, as if one precluded the other. But Sales isn’t anti-sex. She’s pro-intimacy, in favor of girls seeking out the kind of unscripted, unmonitored contact that might allow them to put themselves forward without risking calamitous social censure. As in the first days of dating, Sales suggests that privacy might be best found in public. She closes her book with Eve, a nineteen-year-old college student in Newark, Delaware, who has gone on one date: “The boy had borrowed his friend’s car, picked her up, and driven her to Main Street, ‘and we went out to dinner, and it was just so refreshing. Awkward as hell because I’d never done it before, but it was a real-life thrill. I was like, Holy shit, how do I look? Like I couldn’t plan on what I was going to say to him . . . it’s not like texting. . . . Like you’re here, this is live, this is now. I need that.’ ”

Reading Weigel’s “Labor of Love,” you can get the sense that women are now pinballing among the worst of all the dating systems that have come before. Like the shopgirls of the twenties, Weigel says, we turn ourselves into commodities, typing up dating-site profiles as if they were product descriptions, placing orders on one person and disposing of the next with a single swipe. We drift into reluctant long-term commitments, as the monogamists of the fifties did. Young women are still warned, as the career women of the eighties were, that we’re “dating on a deadline” and have only so much time before our eggs dry up—if we haven’t frozen them, in which case we must not let prospective partners in on the secret, lest they fear entrapment in the plans we’ve worked out for the future.

It’s enough to cause an identity crisis, which is exactly what Weigel says happened to her. “I had no idea who I was,” she writes in the book’s afterword. “And as long as I kept impersonating all the women I thought I should be, I could not receive love, much less give it. I had no self to choose to give it from.” Weigel is hardly alone in making this sad confession. “Do we even know what being in love is?” Eve asks Sales in “American Girls.” “Will we ever get there because we have such a screwed-up notion of what it should be, or how you should get there?”

But dating can be more than a tool by which society bends us to fit its romantic design. It’s also a way of discovering the self, of testing out different lives and different loves. Inevitably, some of those lives crack and dissolve. The self changes, as the self is liable to do. It can be painful, this sloughing off of earlier selves, this reconsidering of earlier desires. It can be necessary, too. In “All the Single Ladies,” Traister celebrates the fact that the average age at which American women first get married is now, at twenty-seven, the highest it’s ever been. Women are taking more time to define the terms of their own lives, single or joined. Traister got married when she was thirty-five, to a man who was a decade older. At that age, she writes, “one of us was not simply going to subsume the other.” In other words, they had selves, ones they wanted to keep and share. The best part of hitting the dating jackpot on the first go-round also sometimes turns out to be the worst: you might get just what you thought you wanted.

At the end of “Labor of Love,” Weigel reveals that she married her husband while writing her book. Yet she says nothing about their courtship. After all her talk about love as labor, and the careful attention she pays to the transactional vocabulary of dating, Weigel describes the circumstances of her own union with the ultimate phrase of romantic effortlessness: she fell in love. Maybe she really did get the job done that easily. You know what they say, though, about how marriage takes hard work. I’ll be keeping an eye out for the sequel. ♦