Asking for a Friend

Three Centuries of Advice on Life, Love, Money, and Other Burning Questions from a Nation Obsessed


By Jessica Weisberg

Read by Karissa Vacker

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A delightful history of Americans’ obsession with advice — from Poor Richard to Dr. Spock to Miss Manners

Americans, for all our talk of pulling ourselves up by our bootstraps, obsessively seek advice on matters large and small. Perhaps precisely because we believe in bettering ourselves and our circumstances in life, we ask for guidance constantly. And this has been true since our nation’s earliest days: from the colonial era on, there have always been people eager to step up and offer advice, some of it lousy, some of it thoughtful, but all of it read and debated by generations of Americans.

Jessica Weisberg takes readers on a tour of the advice-givers who have made their names, and sometimes their fortunes, by telling Americans what to do. You probably don’t want to follow all the advice they proffered. Eating graham crackers will not make you a better person, and wearing blue to work won’t guarantee a promotion. But for all that has changed in American life, it’s a comfort to know that our hang-ups, fears, and hopes have not. We’ve always loved seeking advice — so long as it’s anonymous, and as long as it’s clear that we’re not asking for ourselves; we’re just asking for a friend.



I’LL BEGIN BY GETTING SOMETHING OUT OF THE WAY: I have no clear and easy tricks for a happier, healthier you. I have no instant remedies for sluggishness, or shyness, or social discomfort. I possess no secrets to success. My morning routine, which I am not suggesting you imitate, can be summarized as (1) Wake up. (2) Hurry.

But this book tells the stories of sixteen people who made their names, and sometimes their fortunes, by telling people what to do. They are all professional advice-givers, and their job is to answer Americans’ thorniest, most intimate questions.

You’ve probably heard of many of the individuals profiled in the pages ahead, like Benjamin Franklin, “Dear Abby,” Dale Carnegie, and Elisabeth Kübler-Ross. Others may be new to you, like John Dunton, William Alcott, Dorothy Dix, Sylvia Porter, and Joan Quigley. All of them wrote, in one form or another—books, columns, letters, almanacs—and their words and ideas were so popular that they rumbled across all spheres of American popular culture, their maxims stitched on pillows, printed on mugs, recited at dinner; their faces fixtures on magazine covers and cable channels; and their books docked permanently on the bestseller list. They dislodged long-established norms about how Americans ought to date, mourn, work, and raise their children, and defined, and redefined, what was “right” and what was not.

Most so-called serious writers diagnose but never prescribe. A memoirist might probe her own experience with mourning for her readers’ benefit, but she’s unlikely to offer explicit instructions. Listening to Lena Dunham talk about her struggles as a woman in Hollywood may inspire you, but even she, with her porous definition of personal boundaries, stops short of providing a step-by-step guide. Advice-givers don’t have these hang-ups—as a group, they tend not to have many hang-ups.

And yet few writers come close to possessing the power and influence advice-givers wield. They literally tell people what to do! And people listen! Even though they often aren’t licensed to be giving advice; frequently their only qualifications are their imperviousness to embarrassment and their penchant for popularity. Most of them entertain as they counsel; they are skillful at coining catchy one-liners and composing sentences that play in your mind like a pop song. Often, their advice columns are designed to be playful. There is no telling if correspondents like End of the Line or Losing It are the melancholic people they claim to be or if they are pranksters, or editors making backhanded assignments. Still, columnists have become the arbitrary authors of social rules, helping readers decide what is required of them. After Pauline Phillips, or “Dear Abby,” wrote about the importance of writing a will, hundreds of thousands of people signed one for the first time. With one column, she normalized the idea that preparing for death, while one is still young and healthy, is not morbid but prudent. This book is filled with stories like this, of not particularly credible people issuing mandates that millions of Americans followed.

America is unique in its hankering for advice. The British have their “agony aunts”—their equivalent of advice columnists—but rarely do they reach the same level of prominence as their American colleagues. The American self-help empire has been sprawling aggressively for decades, overtaking bookstores and the internet. It’s estimated that Americans spend eleven billion dollars a year on self-help books. (“Here’s Sound Advice: Write a Book, Become Rich,” went one headline in Forbes.)

This multibillion-dollar industry employs many, many advice-givers. There are experts on finance and car maintenance and dog obedience. But the advice-givers profiled in this book are of a more ambitious ilk: they attempt to provide concrete solutions to the murkiest problems; they are brave—or foolish—enough to seek answers that have escaped philosophers, poets, and religious scholars for centuries, and to bill themselves as experts on topics as broad and impossible as love, health, and life itself.

The typical story about an advice-giver, the one you’ve likely heard before, is about a phony or hypocrite. A person incapable of following his own sage wisdom, who espoused knowledge on subjects like dating or friendship even as he remained perennially single and friendless, or who encouraged moral or fiscal restraint while he was millions in debt with a family on every continent.

Miss Lonelyhearts, the 1933 novel by Nathanael West, is the classic example. It tells the story of an anonymous advice columnist for a New York paper. The novel begins with letters from the people seeking advice from Miss Lonelyhearts: there’s one from a woman being pressured by her husband to have an eighth child against her and her doctor’s wishes, another from a teenage girl born without a nose and bullied by the other teenagers at her school, and one pained letter from a boy who suspects that his deaf-mute little sister was molested and isn’t sure what to do. Each letter is its own distinct melodrama, but their authors are all people who don’t need just advice but an empathetic friend—someone who can say “It’s going to be okay” with conviction. Then we’re introduced to the individual behind Miss Lonelyhearts, who is tasked with performing these significant feats of emotional labor. He is a depressed middle-aged man who dulls his loneliness with alcohol and chain-smoking and despises his colleagues and his readers. He churns out columns dense with mawkish one-liners such as, “When old paths are choked with the debris of failure, look for newer and fresher paths.” Miss Lonelyhearts’s advice is clear and straightforward, presumably helpful to those seeking direction, but also a symptom of the columnist’s own emotional limitations. He’s an expert at dismissing dangerous feelings. “Her sureness was based on the power to limit experience arbitrarily,” West writes of Miss Lonelyhearts.

Straight Talk, the 1992 film starring Dolly Parton, depicts a different kind of ruse: a hick with a heart of gold falls into a job as a radio psychologist in Chicago and claims to hold a PhD though she never went to college. One of the more notable advice-givers from the last few decades is Donald Trump, a person and brand that has become almost synonymous with deceit. (This isn’t a political statement: every reality television star traffics in flash.) Trump’s 1987 bestseller The Art of the Deal painted him as a cautious and expert deal maker, but within five years of its publication, four of Trump’s companies had filed for bankruptcy.

The advice columnists in this book aren’t just hypocrites and narcissists, even if they do display those tendencies once in a while. They’re all well-intentioned people who tend to get in the way of their own noble instincts. Many of them are social reformers who upended the status quo, expanded rights for women and minorities, and proselytized greater acceptance for different ways of living. Dorothy Dix, for instance, was an advice columnist at the turn of the twentieth century who strove to legitimize domestic work, urging wives to strike until their husbands offered them a living wage. All of the individuals in the pages ahead are idealists, eager to change the world, or at least get people to change their behavior. They share a curiosity for giant moral and emotional questions and an instinct for controversy.

I should get something else out of the way: I don’t necessarily recommend that you follow all of the advice in this book. Some of it is extreme, outdated, or downright insane. William Alcott, an early dieting expert, urged his followers to avoid tomatoes under all circumstances. Dorothy Dix advised against divorce, no matter how miserable the relationship had become.

While their wisdom may not always seem relevant today, the advice-givers in this book were all, at some point, responding to Americans’ emotional needs. This book is a history of Americans seeking the answers to their generation’s hardest questions, their parents being just as out of touch as ours are. Their questions are a window into the particular and universal torments of being alive in the 1810s or 1910s or 2010s. I am as interested in the advice-givers as I am in the millions of Americans who needed them.

FIVE OR SO years ago, in my midtwenties, I became disquietingly addicted to an advice column. It was called “Dear Sugar,” and it was published on The Rumpus, a website geared to emerging writers. I was, as they say, “between things”—that joyless euphemism for having more time on one’s hands than one wants. I didn’t know then that “Sugar” was Cheryl Strayed, the novelist and memoirist who would soon publish Wild, a memoir about the months she spent hiking the Pacific Crest Trail. “Dear Sugar” had no clear publishing schedule, so I checked the site every day. I never missed a column. I never sent Sugar a letter, but I felt connected to those who did. They were lonely, too.

If you were looking for straightforward advice, Sugar was not the person to turn to. She would call you a “warrior” or even a “sweet arrogant beautiful crazy talented tortured rising star glowbug,” which may or may not have made you feel better. She would offer you anecdotes—some harrowing, some charming—from her own life, but she was unlikely to tell you what to do. And that was precisely what made her columns so appealing. Sugar was the internet’s greatest relief from itself. The internet is like a garrulous friend—entertaining and inattentive, carrying on regardless of who’s around. Sugar, in turn, liked to listen. Thousands of people wrote to Sugar seeking not her advice but her attention. She received a letter early on in her tenure that went, “WTF, WTF, WTF? I’m asking this question as it applies to everything every day. Best, WTF.” And then other letters like it—vague, existential pleas for Sugar’s companionship—started flowing in. “I don’t have a definite question for you. I’m a sad, angry man whose son died. I want him back. That’s all I ask for and it’s not a question,” one reader wrote, in a letter that went on for pages. She had both male and female readers, but their questions recalled what Betty Friedan, in The Feminine Mystique, called “the problem that has no name.” Friedan wrote about the “strange stirring, a sense of dissatisfaction” among American housewives in the fifties who spent too much of their days alone. Sugar’s readers, similarly, had trouble naming what plagued them. They were self-centered enough to think that their problems merited attention but too shy or unpracticed to ask the right questions. They seem atomized, listless, and chronically lonely. If confronted with this kind of existential angst, Miss Lonelyhearts would have given actionable, straightforward advice. (“Try to have lunch with a friend!”) Sugar, on the other hand, was an aficionado of dangerous, complicated feelings, a glutton for experience. She said “I’m sorry” a lot and offered her condolences in lyrical prose. “How painful. I’m sorry this happened to you,” she told Mourning and Raging, whose husband had cheated on her. “Though we live in a time and place and culture that tries to tell us otherwise, suffering is what happens when truly horrible things happen to us,” she wrote to another advice-seeker.

I wrote above that I was “disquietingly” obsessed with “Dear Sugar.” As far as addictions go, reading is a fairly anodyne one. But advice or self-help, despite its ubiquity, still carries a whiff of shame. It’s an embarrassment, for many, to be caught in the self-help aisle; they would rather be caught reading a worn paperback with a woman in a red bustier on the cover. (Those posing the questions have always been granted anonymity, but even reading these exchanges seems to demand a degree of privacy.) Advice books are considered undignified reading material and, at the same time, too edifying to be excused as a guilty pleasure.

But seeking advice should never be shameful. Needing advice means you have yet to learn something that others seem to know—what to wear to an interview, what to give someone as a wedding present. And not knowing something is a sign that you’re entering a world different from the one in which you were raised, or a world that recently discriminated against people who look like you. We need professional advice because we don’t know any other women in our industry, or because we’re the first person in our family to attend college. Americans’ interest in advice reflects our cultural tendency toward optimism: we tend to believe that with a bit of direction and a small boost, the future can be bright. Seeking advice is for strivers, for people who want to better themselves, land a new job, get in shape.

The fact that Americans want advice is proof that the American dream still exists, at least in people’s imaginations. Who doesn’t want to believe that with hard work, determination, and a bit of advice, that anything is possible? It’s an idea that advice-givers have been peddling for centuries. Benjamin Franklin wrote Poor Richard’s Almanack, his annual compendium of life lessons, with the hopes that anyone, from any background, would be inspired by it.

Over the centuries, the advice changes, as do the people supplying it, but the questions largely remain the same. Should I stay with my husband after learning he’s cheated? How do I get out of debt? How do I seem more confident than I really am? There’s never been a time when life hasn’t been mind-bogglingly hard, or a time when we didn’t hope for someone or something to come along to make sense of it all. The past was never as simple as it now seems. Many of the most confusing questions—How do I mourn my loved one? What’s the secret to a happy marriage?—have been confusing us for hundreds of years.

There is a community of historians concerned with what’s called “emotional history” who study how people throughout time have communicated their feelings. I am not a historian, but I consider this book a work of emotional history, one that examines the flawed and fascinating people who have offered Americans comfort and wisdom over the past three hundred years as well as the people who turned to them when they wanted to be told that everything was going to be fine, when they sought someone—like Sugar—who could say “I’m sorry” and sound like they meant it. History is, typically, a chronology of great accomplishments and the figures who helmed them, but advice columns offer a different kind of history: one that looks at the anxieties quietly suffered by innumerable Americans and that they revealed, exclusively in some cases, to a pseudonymous stranger. In the early twentieth century, many women started advice columns because they offered a rare shot at a byline. The history of advice centers around these influential women who amassed power through their assiduous emotional labor—work that was quintessential to formation of American identity but is rarely, if ever, mentioned in textbooks.

ADVICE-GIVERS HAVE directed their audience to be obedient or rebellious, disciplined or free-spirited, fiercely self-reliant or unfailingly generous, depending on the decade. If you pick up an etiquette book from the 1790s, you will not learn how to be less anxious at a party but how to make those around you enjoy themselves. Particularly during times of war or upheaval, advice-givers stressed the importance of honoring social binds, whereas today the emphasis is more on self-actualization, or “self-help.” Selfishness has gone from a categorical sin to something more complicated, something that can even be worth fighting for.

In the colonial era, advice-giving was the job of the genteel. Today, we want advice-givers to be accessible; we want to be spoken to in the first person. There’s been a cultural shift favoring vulnerability over expertise. This book maps the transformation of the advice-giver from the buttoned-up pundit to the tell-all peer, from Benjamin Franklin to Top Writers on Quora. The barriers to achieving authority—an elusive but necessary quality for those who give advice for a living—have loosened over the past few centuries. There’s always been advice geared toward women or toward specific immigrant groups or ethnic communities—Jewish advice columnists, black advice columnists—but until the twentieth century, advice marketed to a general, all-genders audience was almost exclusively written by white men. In recent years, the internet and podcasting have lowered the barriers for aspiring advice-givers. But aside from Oprah, who politely declined to be interviewed for this book, mass-market life advice is still largely dispensed by white people.

I’ve grouped the advice-givers in this book into four loosely chronological categories. The first group are men who dispensed nonreligious advice from the late 1600s to the mid-1800s, when most social guides were written by preachers or religious scholars. These men referenced the Bible but based their ideas on a range of other texts, conversations with friends, and their own experiences. Even though they were all white, male, and pedigreed, they still grappled with their claims to authority. The second group, mostly women, all worked in the twentieth century and distinguished themselves by striking the tone of a friend, of someone who resembled the reader and related to their pains and fantasies. They sought recognition not for their merits or achievements but for their capacity for empathy. The third group, who also worked in the twentieth century, were experts in their field, possessed PhDs or other impressive credentials, and believed that they were uniquely qualified to give advice in their subject area, whether that be child rearing, mourning, or astrology. The fourth group are contemporary advice-givers, all of whom walk a fine line between friendliness and authority; they want to be relatable, but they also want your respect. Compared to their predecessors, they are far more willing to share stories from their own lives, citing their mistakes to prove their credibility. But they are also quick to formalize their services, bestowing themselves with made-up titles like “life coach” so that they’re not mistaken for laity.

But the most well-received advice-givers throughout history have tended to be those who argue that following your heart too steadfastly is a lonely enterprise, but abiding too closely to external demands will harden you. The goal of most advice, ultimately, is to find a compromise between an individual’s needs and those of the society she lives in. It’s a compromise that fuels America’s most idealized vision of itself: a country where everyone can express their differences but still get along.

part one

Old, Wise Men

There is nothing so beautiful and legitimate as to play the man well and properly, no knowledge so hard to acquire as the knowledge of how to live life well and naturally.

—Michel de Montaigne, Of Experience

THE IDEA THAT THERE IS SOMETHING SUSPECT ABOUT professional advice-givers has a history, and that history begins with John Dunton. In the 1690s, Dunton invented the advice column as we now know it and counseled Londoners on all varieties of spiritual and moral questions. Dunton had never been known as an especially sage or accomplished person. He was a middling publisher, and the resounding consensus among his peers was that he was an acquired taste of a human being. Most of his readers, presumably, had grandfathers, parents, teachers, and pastors they could turn to for guidance; if they were readers, they had the works of Plato and Shakespeare, the Bible. Why, then, seek advice from someone they didn’t know?

Before Dunton, there was no such thing as advice literature. Its closest approximation was philosophy written as a dialogue. Plato originated the form with a series of wide-ranging conversations about love, government, and relationships, most of which feature his mentor, Socrates, replying to his students’ questions. The question-and-answer format is grounding: it turns the philosopher from a high-minded scholar, immersed in a universe of abstractions, into an accessible teacher responding to real-life concerns. (Like nutrition. In one conversation, Socrates recommends a diet heavy in barley, wheat, olives, cheese, and figs.) The conversational format was parroted by many religious scholars and philosophers, such as Cicero and St. Augustine; the Milindapañha, one of the earliest Buddhist texts, was written as a dialogue between a king and a priest. These are not conversations among equals: they are interviews; one person asks the questions, the smarter person responds to them. But there is a sense of trust, of kinship, of being honored to simply be in the room.

Dunton, and the many advice-givers who succeeded him, was never in the same room as the people who sought his advice. The exchanges occurred anonymously and by mail. Dunton was a skillful pitchman who had the instinct to sell his readers on a completely new kind of intimacy—intimacy among strangers. He recognized that though it is ennobling to be in the room among scholars, to be cradled by one’s mentors and guides, there is something uniquely freeing about a correspondence among strangers, whose judgments can be kinder or blunter than those of a close friend and whose opinions bear a detachment that can feel like omniscience. He realized, many centuries before the invention of the internet, that it can be easier to trust someone who has no reason to care. There are no humiliations, no dumb questions, in this nameless, epistolary space.

In the late 1680s, just before Dunton began his advice column, King James II was ousted in a coup and replaced by his son-in-law. The other three men in this section, Lord Chesterfield, Benjamin Franklin, and William Alcott, rose to prominence during similarly turbulent moments in history. War, in any decade, has a theatrical quality, requiring citizens to perform temporary roles in the name of patriotism: teenage boys become soldiers, women join the workforce. Lord Chesterfield was an accomplished British statesman, but in his role as a politician, he had no influence on America—he never even visited the colonies. But his book arrived in America in 1775, a time of profound open-mindedness and upheaval, when readers were hungry for new ideas, when any book could be The Book. Benjamin Franklin, too, found a ready audience in prerevolutionary America. Amid the chaos of Philadelphia, which was the second-largest city in the colonies and had no newspaper, fire department, or hospital, Franklin created a new role for himself—the secular moralist, the policeman of everyday ethics—and found a ready audience. Some decades later, William Alcott, a doctor and an early evangelist for vegetarianism, wrote nutritional advice during the lead-up to the Civil War and connected his theories on healthy eating to the abolitionist movement.

These men provided advice at a moment when power was newly splintered and available for the taking. They were each deliberate in their plans to acquire some for themselves. They were experimenting with new ideas, nothing blasphemous, but different from what your father or pastor would tell you. They were not fire-breathing activists—the status quo had treated them well. But they initiated conversations that weren’t happening elsewhere.

None of them were terribly concerned about their lack of qualifications. They were all preternaturally confident. They did not have elaborate arguments or any great evidence for why everyone should take their word on how to behave. Trust me, they said, essentially. And people did.


In Praise of the Maggot

John Dunton

THERE WAS ONCE A GROUP OF MEN WHO HAD THE answer to every question. They were based in London and called themselves the Athenian Society. Membership was kept secret, but they claimed to be thirty-odd strong and to include experts in religion, astronomy, math, and philosophy. From 1691 to 1697, with the occasional hiatus, the Athenian Society published the Athenian Mercury, a twice-weekly magazine in which members responded to readers’ questions. Their readers wanted to know why alcohol killed erections and made people slur, why horse excrement was square, if people born with missing body parts were also missing pieces of their soul, and if the sun was made of fire. They also asked ethical, “was it okay” questions. Like, was it okay for a man and woman to live together before they were married, or to have adulterous thoughts if you never acted on them, or to masturbate, or to throw a witch in a pond, or for a Jew to marry a Christian? The Athenians delivered harsh and clear determinations of what was acceptable and what was not. They showed the moral clarity of a priest and the worldliness of a diplomat. They condemned adultery, masturbation, mixed marriages, and impure thoughts.

The Athenians’ founder, John Dunton, was a publisher with a small bookstore in the Poultry, an industrial London neighborhood named for its unwelcoming smell. He was known to be impatient and arrogant. He had few friends. A colleague once described Dunton’s mind as being like a “table, where the victuals were ill-sorted and worse dressed.” In portraits, he appears gangly, with a pointy nose and a bulbous chin and a face so narrow that it’s unclear, if he were to smile, where a smile might fit.

In his memoir, Dunton writes that he learned to lie before he learned to speak. In elementary school, in a small town near London, he paid no attention to the teacher and instead perfected the art of avoiding things he did not want to do. “The advances I made in school went on very slowly,” he writes. “For I had a thousand little things to say, that would excuse my absence or at least abate the rigor of punishment.” He was a serial daydreamer who spent days lost in his own detailed fantasies and armchair adventures. He had an instinct for “rambling.” “I have been a Rambler ever since I was 14 years Old,” Dunton wrote. “I was always moving from one Stage to another, rummaging every corner and neuke [nook] of the World.” Dunton didn’t actually travel all that much, but he was fidgety and restless and had an especially vivid strain of wanderlust.

Dunton’s mother died when he was a baby and he was raised by his father, an Anglican minister from a long line of Anglican ministers. His father likely assumed that John would join the clergy, but by his teenage years, it must have been obvious that he lacked the discipline for religious life. When he was thirteen, Dunton had such a raving crush on a girl in the neighborhood that he couldn’t bring himself to study or pay attention to his classes. Finally, when he was fifteen, his father allowed him to drop out of school and found him an apprenticeship with a religious bookseller in London.


  • "Take my advice and read this fascinating book immediately. It's the only piece of advice I can offer that even begins to compare to the advice of the writers it chronicles. Whether it's Benjamin Franklin, Dr. Spock, or 'The King of Quora,' Jessica Weisberg captures her subjects' work and personalities with engaging insight. As she does so, she also offers an illuminating look into what society craves advice on in any given age (from retaining your job in the 1930s to retaining your marriage in the 1990s). It's a must read for anyone who loves learning about history and human angst, as well as those who love their local paper's advice column."—Jennifer Wright, author of It Ended Badly: 13 of the Worst Breakups in History
  • "Rich with insight and surprising facts, Jessica Weisberg's ingenious appraisal of America's guidance-givers doubles as a wholly unexpected history of our national psyche. At long last, the lowly advice column gets its due!"—Kate Bolick, author of Spinster: Making a Life of One's Own
  • "An oddly soothing antidote to the millenarian terrors of today, Jessica Weisberg's history of ordinary American anxiety is as warm, funny, entertaining, and chattily insightful as the advice-dispensers she portrays. In the centuries before the internet, these were the ones we turned to with questions so obscure, embarrassing, weird, or mortifyingly personal that only a stranger would do."—Larissa MacFarquhar, authorof Strangers Drowning: ImpossibleIdealism, Drastic Choices, and the Urge to Help
  • "Jessica Weisberg's hilarious, enlightening odyssey through the history of advice columns chronicles the evolution of our anxieties over how to act. However weird or offensive some of our questions have been, it's heartening to know that at least we've always been trying. A surprising and delightful read."—Mac McClelland, author of Irritable Hearts: A PTSD Love Story
  • "Welcome to a hilarious dinner party of outrageous characters! Each one of Weisberg's profiles is like a witty, surprisingly profound toast. I can't stop talking about this book to everyone I know; it snuck up on me as one of the most insightful books about human nature that I've ever read."—Courtney E.Martin, author of The New Better Off:Reinventing the American Dream

On Sale
Apr 3, 2018
Hachette Audio

Jessica Weisberg

About the Author

Jessica Weisberg is an award-winning writer and producer. Her writing has appeared in the New Yorker, New York Times, Harper’s, and Atavist, among other publications, and been nominated for a National Magazine Award. She was a producer on the podcast Serial and runs the features unit at Vice News Tonight on HBO, for which she’s been nominated for an Emmy. She lives in Brooklyn.

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