Dating “often feels like the worst, most precarious form of contemporary labor: an unpaid internship,” Moira Weigel writes. Illustration by Alain Pilon

Suzanne, a young woman in San Francisco, met a man—call him John—on the dating site OKCupid. John was attractive and charming. More notably, he indulged in the kind of profligate displays of affection which signal a definite eagerness to commit. He sneaked Suzanne’s favorite snacks into her purse as a workday surprise and insisted early on that she keep a key to his apartment. He asked her to help him choose a couch and then spooned with her on all the floor models. He even accompanied her, unprompted, to the D.M.V.—an act roughly equivalent, in today’s gallantry currency, to Perseus rescuing Andromeda from the sea monster.

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.