From ancient Rome to the pickup artist era—a curated list with commentary from my research into the evolution of dating advice
Essential dating books
Some dating books sell millions of copies and vanish without a trace. Others reshape how an entire generation approaches romance. After a decade spent building an archive of over 500 dating and relationship guides, I’ve identified ten books that didn’t just reflect their era—they changed behavior. Here they are, in chronological order.
1. Ars Amatoria by Ovid (2 AD)
The original pickup guide. Ovid’s three-book poem offered tactical advice on seduction in Augustan Rome—where to meet women (the theatre, the races), how to approach them, and how to keep them interested. Book III even addressed women directly, advising them on how to attract and hold male attention.
What makes the Ars Amatoria remarkable is how modern it feels. Ovid understood that desire is psychological, that scarcity increases value, and that love can be systematized. The poem was so influential—and so scandalous—that it may have contributed to his exile. It was burned in Florence in 1497 and seized by U.S. Customs in 1930. Yet every strategic dating book since is essentially a footnote to Ovid.
3. Ideal Marriage by Theodoor van de Velde (1926)
A Dutch gynecologist’s bold sex manual redefined marital intimacy by placing women’s sexual pleasure front and center. At a time when sex in marriage was often seen as a procreative duty owed by wives, Theodoor Hendrik van de Velde argued that true harmony required husbands to master technique and prioritize their partners’ satisfaction—declaring that “mutual orgasm must be almost simultaneous” for the “ideal” union. The book, which blended clinical detail with practical advice on foreplay, positions, and communication, sold well over half a million copies and has remained a go-to reference on sexual compatibility for decades.
Building on trailblazers like Marie Stopes’s Married Love (1918), van de Velde’s manual cemented the idea that sexual fulfillment was learnable, mutual, and essential to lasting happiness. Its influence echoes in every modern discussion of bedroom equality, open communication, and sex as a skill worth cultivating.
3. How to Win and Hold a Husband by Dorothy Dix (1939)
Before Dear Abby, before Ann Landers, there was Dorothy Dix (aka Elizabeth Meriwether Gilmer). Gilmer’s advice column ran for fifty-five years and reached sixty million readers worldwide—making her America’s highest-paid and most widely read female journalist at the time of her death. How to Win and Hold a Husband, with a foreword by Dale Carnegie, distilled decades of counsel into book form.
What gave Dix’s advice its edge was her own disastrous marriage. Her husband suffered from mental illness and spent years institutionalized before dying in an asylum in 1931. She knew firsthand that romance could curdle, and her advice reflected it: don’t love your husband too much or at least don’t let him know if you do. Make him feel he has to work to keep your affections. Demand decent treatment and be willing to leave if you don’t get it. Her counsel was strategic rather than sentimental—she treated marriage as a game that required skill to win. In an era when women had fewer economic options, Dix offered something radical: practical instruction for navigating marriage with your dignity intact.
4. Sex and the Single Girl by Helen Gurley Brown (1962)
Before Helen Gurley Brown transformed Cosmopolitan into the voice of the sexually liberated single woman, she wrote this manifesto. Sex and the Single Girl told unmarried women that they could—and should—have careers, apartments, money, and lovers. Marriage was an option, not a necessity.
The book was both scandalous and a runaway sensation, selling over two million copies in its explosive early run. It granted a generation permission to embrace singledom without shame. Brown’s proto-feminist vision was undeniably tangled—laced with relentless advice on dieting, grooming, and mastering the art of captivating men—but its revolutionary spark endures: single women weren’t pathetic “failed wives-in-waiting.” They were vibrant, desiring individuals with full lives and agency of their own. As Brown herself quipped, “Good girls go to heaven, bad girls go everywhere.”
5. The Total Woman by Marabel Morgan (1973)
Marabel Morgan’s guide for Christian wives became the bestselling nonfiction book of 1974, yet its legacy rests largely on advice she never gave. The notorious instruction to greet your husband at the door wrapped in Saran Wrap? Morgan never wrote it—though the myth persists in popular culture, from the sitcom Maude to Fried Green Tomatoes. What Morgan actually wrote was more interesting: values clarification exercises, time management techniques for housewives, and practical advice about sustaining desire within marriage. She was attacked from both sides—Time called her a “Christian Whore,” feminists dismissed her as “Hogwash and Bullshit”—yet she sold over three million copies in her first year.
The Total Woman succeeded because it acknowledged what sexual liberation tried to deny: that many women responded to traditional masculine displays and that millions of housewives felt feminism had left them without a script for marriage. Her advice about seduction wasn’t submission but strategic signaling—maintaining sexual value to sustain male investment. The feminist backlash revealed a central paradox of liberation: women wanted freedom from traditional roles but often continued responding to men who embodied them.
6. Men Are from Mars, Women Are from Venus by John Gray (1992)
John Gray didn’t invent the idea that men and women communicate differently, but he packaged it into the most successful relationship book of the 1990s. The planetary metaphor was simplistic but sticky: men and women are so different they might as well be from different planets.
The book’s influence was enormous and double-edged. On one hand, it gave couples a shared vocabulary for discussing miscommunication. On the other, it encouraged essentialist thinking that could excuse rather than address problems. Love Gray or hate him, his framework shaped how millions of people understood—and sometimes misunderstood—their partners.
7. The Rules by Ellen Fein and Sherrie Schneider (1995)
I’ve written about The Rules elsewhere, but its inclusion here is non-negotiable. Fein and Schneider codified “playing hard to get” into an explicit 35-rule program: don’t call him, don’t see him more than twice a week, always end dates first.
The book was attacked as retrograde and celebrated as empowering, sometimes by the same critics. What’s undeniable is that it changed behavior. Millions of women consciously adopted the Rules framework, and its influence persists in every piece of advice about “not being too available.” Whether this was progress or regression remains hotly debated.
8. The Game by Neil Strauss (2005)
Neil Strauss’s memoir of infiltrating the pickup artist community introduced terms like “negging,” “peacocking,” and “the approach” to mainstream culture. The book presented seduction as a learnable skill set, complete with techniques, coaches, and a competitive subculture.
The Game was influential in ways Strauss later seemed to regret. It spawned an industry of pickup coaches and online forums that, at their worst, veered into misogyny. But it also surfaced a genuine insight: many men felt lost in modern dating and were desperate for guidance. The book’s legacy is contested, but its cultural impact is undeniable.
9. Attached by Amir Levine and Rachel Heller (2010)
This book brought attachment theory—the idea that early childhood relationships shape adult attachment styles—to a mass audience. Levine and Heller argued that people fall into three categories: secure, anxious, and avoidant. Understanding your style could transform your relationships.
Attached gave readers a new diagnostic vocabulary. Suddenly everyone was identifying themselves and their partners as anxious or avoidant, using the framework to explain patterns that had previously seemed mysterious or personal. Whether the framework oversimplifies is debatable; that it changed how millions discuss relationships is not.
10. Models by Mark Manson (2011)
Mark Manson’s guide positioned itself against the manipulative tactics of the pickup artist community from which it emerged. His core argument: authentic vulnerability and honest self-expression are more attractive than rehearsed techniques. Be genuinely interesting, work on your life, and approach dating from abundance rather than desperation.
Models influenced a generation of men exhausted by the gamification of The Game and its imitators. It offered a path that felt both effective and ethical—self-improvement without manipulation. The book anticipated Manson’s later blockbuster, The Subtle Art of Not Giving a F*ck and helped shift men’s dating advice exclusively away from tactics and toward character.
What these books share
Each of these books, whatever its flaws, identified something true about its moment. The best dating advice doesn’t just tell people what to do—it articulates tensions they’re already feeling and offers a framework for resolution. The books that change behavior are the ones that name a problem readers recognized but couldn’t quite articulate.
That’s the tradition I’m trying to continue with Costly Signals: not another set of rules, but a framework for understanding why certain approaches work, why others fail, and how to build something authentic in a world of performed connection.
Andrew King is the author of Costly Signals: The Evolution of Dating Advice. His research archive spans over 500 dating and relationship books from the 1800s to the present.
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