Not long after my partner and I exchanged our first “I love you”s, I made an embarrassing confession. In the weeks leading up to the occasion, I had Googled how long one should wait before declaring their love, and combed through dozens of forums and articles in search of guidance. With relief, my partner blurted out: “I did the same thing!” I imagined us both whispering our mutual question into the search bar, seeking a faceless chorus of counsel.

We were far from the first to anonymously seek romantic prescriptions from strangers. In 1694, a lovelorn inquirer wrote to The Athenian Mercury, a periodical published by the English printer John Dunton, with a question not unlike mine: “A lady who is in love desires to know how she may decently convince the other person of her passion?” The response she received from the paper’s team of experts—that is, Dunton and his two brothers-in-law, under the guise of the “Athenian Society”—was surprisingly sympathetic: “Indeed, Madam, it’s a ticklish point,” they replied, “and you should know a man well before you try anything … To be plain with you, we find men to be an ungrateful sort of animal in such cases … But the best way will be to do it as decently as you can.”

The Athenian Mercury, which consisted entirely of questions and answers, ran for six years starting in 1691 and received thousands of inquiries, many of them attempts at sussing out the tacit rules of dating and romance. As the historian Mary Beth Norton writes in the introduction to her delightful new book, “I Humbly Beg Your Speedy Answer,” which collects and comments on a wide array of Q&As from the paper, many questioners invoked dilemmas that still vex people today: how to manage unrequited affections; how to extract oneself from a regrettable entanglement; how to recover from being “slighted,” or ghosted, by your beloved. (Though not all are so relatable: One woman wrote in 1693 that she “had the misfortune to have a young gentleman fall in love with me to such a degree that he became distracted and died.”)

Dispensing relationship advice was far from Dunton’s mind when he launched the paper, which he referred to as “the question project.” About half a century before Diderot’s Encyclopédie, and three centuries before the invention of Google, Dunton intended to cater to the learned male patrons of London’s new coffeehouses, who sought to educate themselves on subjects including science, medicine, and law. Readers sent in many such questions (“What is a star?” “What causes smallpox?” “Dancing, is it lawful?”), but the format naturally appealed to the perennial, very human confusion about how to navigate sex, love, and marriage. Soon enough, Dunton and his co-editors were flooded with queries such as “How shall a man know when a lady loves him?” and “Who are wisest, those that marry for love or for convenience?”

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Although both men and women wrote to The Athenian Mercury for romantic advice, Norton notes, Dunton tended to group questions about personal relationships under “ladies issues.” More than 300 years later, relationship-advice columns are still often dismissed as frothy features of women’s magazines. But throughout their long history, they have evolved in complicated ways, reflecting the winding path of gender politics—even as they have remained true to a single constant: Love is confusing and hard.

Two of the most popular advice columns of the 20th century—Elizabeth Gilmer’s “Dorothy Dix Talks,” which ran from 1896 to 1950, and Elsie Robinson’s “Cry on Geraldine’s Shoulder,” which doled out answers from 1920 to 1961—were informed by their authors’ own experiences in unhappy marriages, as well as their relatively progressive views of women’s rights. Their widely syndicated columns had major influence. In Asking for a Friend, Jessica Weisberg argues that Dix wielded outsize power over romantic norms. Weisberg cites a 1929 study on cultural mores in Muncie, Indiana, which found that Dix’s column helped dictate townspeople’s ideas about marriage—among them the notion that a wife should be more than “a domestic drudge.”

Robinson, for her part, advocated explicitly for gender equality. “I’m tired of hearing the differences of men and women emphasized and exploited,” she wrote in 1922. “It has built a wicked wall between the sexes and it’s time we knocked it down.” According to Listen, World!, Julie Scheeres and Allison Gilbert’s book about the columnist, Robinson recognized that women were often made to feel frivolous and isolated; she offered them a much needed sense of affirmation. “Is your husband or your complexion growing dull?” she wrote in her announcement for “Cry on Geraldine’s Shoulder.” “Let us then discuss the value of soft soap on complexions—and husbands … We shall sit together on the edge of the world. You have wanted a friend. I’M IT.”

But advice columns have not always been sources of validation and solidarity. Despite her relatively liberal leanings, Dix was also “a stern foe of sexual irregularity among her readership,” per a 1936 profile in Time magazine. As for the advisers behind The Athenian Mercury, they shared what Norton calls “a broadly based Protestant outlook” and often frowned on what they deemed sexual misbehavior, including homosexual relationships and premarital sex.

Some of the more insidious romantic-advice columns in the U.S. flourished after World War II, with the aim of disciplining women dissatisfied by marriage, who were beginning to articulate “the problem that has no name” years before The Feminine Mystique. In No Fault, her memoir about divorce, Haley Mlotek discusses the history of such columns, including “Can This Marriage Be Saved?,” which ran in Ladies’ Home Journal from 1953 to 2014. In the early decades of the column, the answer to the titular question was nearly always yes, no matter how severe the wife’s grievance. (The first columnist behind it, Paul Popenoe, was a known eugenicist whose zeal for marriage stemmed from a desire to propagate the “fit”—that is, middle-class, able-bodied white people.) When a feminist collective staged a sit-in at the magazine’s offices in 1970 demanding to edit a “liberated” issue of the Journal, it decided to rename “Can This Marriage Be Saved?” to “Should This Marriage Be Saved?” (One member reportedly suggested that they simply shorten it to the more declarative “Can This Marriage.”)

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Indeed, over the past century, many romantic-advice columns have functioned as one tentacle of what the scholar Jane Ward calls the “heterosexual-repair industry,” which peddles advice based on the irreconcilable differences between straight men and women. “Marriage experts recognized men’s disinterest and violence toward women, and women’s resentment and fear of men, as fundamental obstacles for straight relationships,” Ward writes in The Tragedy of Heterosexuality. As a result, Ward argues, early advice givers were more interested in perpetuating heterosexual unions—that is, framing men and women’s mutual illegibility as natural—than in trying to improve gender relations. Notably, centuries earlier, the Athenian Society had urged women to be more skeptical of men—“the inconstancy, levity, and prejudices of our own sex being so very notorious”—rather than simply accept their faults.

Today, the lovelorn more frequently eschew the authority of columnists in favor of crowdsourced advice. (I, for one, consulted a Quora forum as well as a number of magazine articles to answer my question.) As a result, relationship guidance has become more democratic but also more diffuse. On the subreddit r/relationship_advice, which has 16 million members, single posts can draw hundreds of responses, many of them conflicting. The greater autonomy people have today to make their own romantic decisions can feel simultaneously empowering and confusing. What’s more, many people are dogged by the suspicion that they’re living through the nadir of heterosexual love, which appears to be buckling under various pressures: Many men are falling behind educationally and economically, and, for some people, the logic of optimization has made dating feel like a chore. Where, internet denizens wonder, have all the “real lovers” gone?

But reading “I Humbly Beg Your Speedy Answer” confirms that even when the norms of courtship and marriage were far more codified, and options in love and life were far more limited, dating was still an anxiety-riddled endeavor. “There are indeed so many equivocations in love that it’s much easier to be in the wrong than in the right,” the Athenian Society wrote to a reader who asked how a woman can tell whether a man is courting her “for marriage or for diversion.” There was no code to crack, no hack to deploy. Romance is, after all, the ultimate test of one’s judgment—which is why we so often outsource that deliberative labor and defer to the advice of others. But, as the Athenian Society told an inquirer in 1692, one thing remains as certain as ever: “If you’re a true lover, you can’t despair at a little hardship.”