Americans are now considered prime candidates for dating from age 14 or younger to close to 30 or older. That’s about 15 years, or roughly a fifth of their lives. For an activity undertaken over such a long period of time, dating is remarkably difficult to characterize. The term has outlasted more than a century’s worth of evolving courtship rituals, and we still don’t know what it means. Sixth-graders claim to be dating when, after extensive negotiations conducted by third parties, two of them go out for ice cream. Many college students and 20‑somethings don’t start dating until after they’ve had sex. Dating can be used to describe exclusive and nonexclusive relationships, both short-term and long-term. And now, thanks to mobile apps, dating can involve a succession of rendezvous over drinks to check out a dizzying parade of “matches” made with the swipe of a finger.

The purpose of dating is not much clearer than its definition. Before the early 1900s, when people started “dating,” they “called.” That is, men called on women, and everyone more or less agreed on the point of the visit. The potential spouses assessed each other in the privacy of her home, her parents assessed his eligibility, and either they got engaged or he went on his way. Over the course of the 20th century, such encounters became more casual, but even tire kickers were expected to make a purchase sooner rather than later. Five decades ago, 72 percent of men and 87 percent of women had gotten married by the time they were 25. By 2012, the situation had basically reversed: 78 percent of men and 67 percent of women were unmarried at that age.

The obvious reason for declining marriage rates is the general erosion of traditional social conventions. A less obvious reason is that the median age for both sexes when they first wed is now six years older than it was for their counterparts in the 1960s. In 2000, Jeffrey Arnett, a developmental psychologist at Clark University, coined the term emerging adulthood to describe the long phase of experimentation that precedes settling down. Dating used to be a time-limited means to an end; today, it’s often an end in itself.

Yet the round-robin of sex and intermittent attachment doesn’t look like much fun. If you’re one of the many who have used an online dating service (among those “single and looking,” more than a third have), you know how quickly dating devolves into work. Tinder’s creators modeled their app on playing cards so it would seem more like a game than services like OkCupid, which put more emphasis on creating a detailed profile. But vetting and being vetted by so many strangers still takes time and concerted attention. Like any other freelance operator, you have to develop and protect your brand. At its worst, as Moira Weigel observes in her recent book, Labor of Love: The Invention of Dating, dating is like a “precarious form of contemporary labor: an unpaid internship. You cannot be sure where things are heading, but you try to gain experience. If you look sharp, you might get a free lunch.” In Future Sex, another new examination of contemporary sexual mores, Emily Witt is even more plaintive. “I had not sought so much choice for myself,” she writes, “and when I found myself with total sexual freedom, I was unhappy.”

We are in the early stages of a dating revolution. The sheer quantity of relationships available through the internet is transforming the quality of those relationships. Though it is probably too soon to say exactly how, Witt and Weigel offer a useful perspective. They’re not old fogies of the sort who always sound the alarm whenever styles of courtship change. Nor are they part of the rising generation of gender-fluid individuals for whom the ever-lengthening list of sexual identities and affinities spells liberation from the heteronormative assumptions of parents and peers. The two authors are (or in Weigel’s case, was, when she wrote her book) single, straight women in their early 30s. Theirs is the “last generation,” Witt writes, “that lived some part of life without the Internet, who were trying to adjust our reality to our technology.”

Weigel, a Ph.D. candidate in comparative literature at Yale, embarked on her charmingly digressive, nonacademic history of American dating after being strung along by a caddish boyfriend torn between her and an ex-girlfriend. His confidence that he was entitled to what he desired (even if what he desired was to be indecisive), compared with her inability to assert her own needs, dismayed her. How retrograde! The sexual revolution had failed her. “It did not change gender roles and romantic relationships as dramatically as they would need to be changed in order to make everyone as free as the idealists promised,” she writes. To understand how she, and women like her, came to feel so dispossessed, she decided to investigate the heritage encoded in the rituals of dating.

Witt, an intrepid journalist and mordantly ambivalent memoirist, looks forward rather than back. With no serious boyfriend in sight—“love is rare,” she writes, “and it is frequently unreciprocated”—she set out to examine alternatives to a “monogamous destiny,” eager for a future in which “the primacy and legitimacy of a single sexual model” is no longer assumed. Adopting the role of participant-observer, she moves through an assortment of sexual subcultures. Many of these are artifacts of the internet, from online dating to sadomasochistic feminist pornography sites to webcam peepshows such as one called Chaturbate. She hopes to find clues about what relationships might look like in a postromantic, postmarital age.

Neither Witt nor Weigel is naive or nostalgic. If you tested them on their knowledge of Jane Austen and gender theory, they’d almost certainly get A’s. They understand that mating practices have always reflected economic conditions and been openly transactional for women whose lives and livelihoods depended on their outcome. I imagine the two authors as undergraduates writing papers about the romantic ideal as an ideological construct and bridezilla weddings as its death throes. But life isn’t graduate school. It’s life. As knowing as they are, Witt and Weigel start their projects feeling “lonely, isolated, and unable to form the connections we wanted,” in Witt’s words, and they know other women feel the same way. Both of them want to discover more-authentic ways to bond.

As Weigel tells it, dating is an unintended by-product of consumerism. Nineteenth-century industrialization ushered in the era of cheap goods, and producers needed to sell more of them. Young women moved to cities to work and met more eligible men in a day than they could previously have met in years. Men started taking women out to places of entertainment that offered young people refuge from their sharp-eyed elders—amusement parks, restaurants, movie theaters, bars. “The first entrepreneurs to create dating platforms,” Weigel calls their proprietors. Romance began to be decoupled from commitment. Trying something on before you bought it became the new rule.

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Then as now, commentators fretted that dating commercialized courtship. In the early 20th century, journalists and vice commissioners worried that the new custom of men paying for women’s dinners amounted to prostitution. Some of the time it surely did—just as today, some dating websites, like SeekingArrangement, pair “sugar babies” with “sugar daddies” who pay off college debts and other expenses. “Ever since the invention of dating, the line between sex work and ‘legitimate’ dating has remained difficult to draw,” Weigel writes. Well before app users rated potential partners so ruthlessly, daters were told to “shop around.” They debated whether they “owed” someone something “in exchange for” a night out. Today, as Weigel notes, we toss around business jargon with an almost transgressive glee, subjecting relationships to “cost-benefit analyses” and invoking the “low risk and low investment costs” of casual sex.

Weigel worries that the naked mercantilism of recreational sexual encounters coarsens us and reinforces stereotypes. Those who try to wriggle out of the old gender roles end up skittish and confused. “Most of my friends agreed that dating felt like experimental theater,” Weigel writes. “You and a partner showed up every night with different, conflicting scripts. You did your best.” Dating may have morphed into improv, but that hasn’t made matters easier for women. If anything, today’s sexual norms favor men. Women must cope with two intense time pressures: to make a good impression in a matter of seconds, and to pair off before the biological timer runs out. Now more than ever, they have to discipline their bodies and restrain their longings—avoid being “too fat, too loud, too ambitious, too needy,” in Weigel’s words.

Witt, too, is impatient with the failure of gender equality to create sexual equality. Even adventurous women, she notes, still take on the bulk of whatever emotional burden comes with casual sex—“trying to control attachment, pretending to enjoy something that hurt or annoyed them, defining sexiness by images they had seen rather than knowing what they wanted.” She’s looking for an empowered version of uninhibited sexuality, or free love, as it used to be called. Oddly, though, the free love she finds is rarely free. Witt mostly trains her attention on sexual interactions that are explicitly commercial. (The exceptions are a polyamorous threesome and Burning Man, the sex-and-drugs-and-self-actualization festival held yearly in the Nevada desert.) She wants to know whether women who use sex to make money, or who exploit men for pleasure, somehow develop more sexual confidence, have a greater sense of sexual agency.

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A writer of many registers, Witt conveys amusement, bemusement, disgust, and sympathy all at once. She fights her reluctance to go on dates arranged through OkCupid, and ends up enjoying some of them. She befriends women who do a great many strange things in exchange for micropayments from customers on Chaturbate (baking cupcakes with bared breasts; telling followers about one’s existential crises while sitting nude on a bed). Witt lets one of these women talk her into doing her own show, though Witt is too nervous to do more than chat with a man who is lying in bed naked except for a pair of Ray-Bans.

She goes further at OneTaste, an organization that sells workshops on something called orgasmic meditation, which is meant to train people, particularly women, to focus on their own sexual pleasure without the distraction of emotions, expectations, and inhibitions. Witt signs up for stroking sessions—15 minutes of clitoral manipulation—which she receives at the hands of Eli, an Apple employee turned OneTaste staff member. The first time he strokes her, she experiences a “deep, intense comfort” that she traces to her neither wanting nor being required to have sex with Eli; when she has an orgasm during the third session, she’s left feeling sad. OneTaste is obviously preying on the sexual desperation of the lonely, but Witt also gives its practitioners credit for trying to “arrive at a more authentic and stable experience of sexual openness … Their method was strange, but at least they believed in the possibility.”

Delving into the deep web and its more extreme forms of pornography, Witt discovers not just the reinforcement of oppressive standards but also their subversion—“a wilderness beyond the gleaming edge of the corporate Internet and the matchstick bodies and glossy manes of network television.” In addition to the usual bondage and discipline, this sexual hinterland features bushy pubic hair, tattoos, bodily fluids, Mexican wrestling masks, birthday cake, ski goggles, and more. The indexes on fetish-specific sites include big clit, chubby, puffy nipples, farting, hairy pussy, fat mature, and ugly. Witt is taken aback by her own positive response. “In looking through all this I found unexpected reassurance that somebody will always want to have sex with me,” she writes. “This was the opposite of the long road toward sexual obsolescence that I had been taught to expect.”

But what about the road toward greater sexual equality? I hope I don’t sound like an alarmed old fogy when I say that the lessons Witt takes away from her journey aren’t very comforting. I doubt many people will share her hopes for the future of marriage and love. Witt, consistent in her ambivalence, doesn’t sound too enthused about them herself. Marriage could be downgraded to a joint custodial venture for the raising of children. We could practice “the emotional management of multiple concurrent relationships.” That doesn’t sound fulfilling; it sounds exhausting. It’s telling that the only time Witt finds joy is at Burning Man, the pop-up city that she recognizes for what it is: “rich people on vacation breaking rules that everyone else would suffer for if they didn’t obey.” Still, the psychedelic drugs, the guru, the instant bond with the guy she meets and accompanies to the orgy dome—the experience “felt right” to Witt, and inspires a tentative vision of a more unfettered sexuality. Perhaps the generation after hers would “do their new drugs and have their new sex. They wouldn’t think of themselves as women or men. They would meld their bodies seamlessly with their machines, without our embarrassment, without our notions of authenticity.” Well, maybe. But then what?

Weigel, by contrast, doesn’t give up on the quest for lasting affection. She has no brave new world to propose, just some fixes for the current one. As her historical survey makes clear, love will never rid itself of economic considerations. Her advice for today’s daters is to embrace the fact that dating is indeed a transaction, that it involves work. Only then can they focus on making the change that counts: approaching romance not as a consumer but as a would-be producer. What would they produce? Care. “Love consists of acts of care you can extend to whomever you choose, for however long your relationship lasts,” Weigel reminds her readers. Yes, care involves as much labor as pleasure, but it’s the best kind of labor there is. The future—our future and the next generation’s—depends on it. If dating for women and men alike became less callow and more careful, less like a shopping spree and more like training for the rigors of intimacy, maybe the whole business wouldn’t be so unsatisfying.


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