When I was 26, in the late 1990s, I met a very handsome man as he was unloading Danish credenzas from his pickup into a vintage-furniture shop he owned in Brooklyn. I’m from West Virginia: show me a sweaty man with a dangerously overloaded truck, and I’m immediately smitten.

This was right after the 1995 publication of The Rules: Time-Tested Secrets for Capturing the Heart of Mr. Right. The Rules was a dating guide, a set of instructions on what to do and not do to catch a man. Above all, women were to be passive (Rule No. 2: “Don’t Talk to a Man First”) undemanding (Rule No. 17: “Let Him Take the Lead”), and above all happy and busy, breezy and lighthearted.

The paperback version hit the New York Times best-seller list the following year. Rules support groups for women sprang up around the country. The book prompted a screaming match on Oprah’s show; she devoted a whole episode to the topic of “do The Rules work or don’t they?” The authors, Ellen Fein and Sherrie Schneider, built a business offering phone consultations and in-person seminars, spreading the gospel of steely passivity to lovelorn women.

I hoped The Rules, however flawed, would offer a scaffold upon which to build a romance

The Rules was roundly denounced by feminists — “I asked my boyfriend out!” hollered a woman on Oprah — by my friends, and by, well, nearly everyone I respected. But the book struck a nerve. “Men do like a challenge!” people would say ruefully. I recently told a friend that it was the 20th anniversary of The Rules, and she whispered, “The crazy thing is, most of that book was right.”

The Rules is a rather incoherent mashup of good, practical advice (don’t waste your energy on someone who’s not interested), retro gender essentialisms (men don’t like funny women), and bizarre anecdotes (Bruce and Jill went bed shopping together for her apartment, and to prove she wasn’t angling for marriage, Jill bought a single bed instead of the queen-size bed, which worked, because then they got married, and then they had to buy a queen-size bed, hah-hah-hah. What adult buys a single bed?).

But the overall theme, presented to you as lovingly as your captor might tuck you in at night, is: adjust to men’s needs. Be someone different from who you are. Squash your own desires. To wit: In bed, “don’t be a drill sergeant, demanding that he do this or that. … Remember, those are your needs you’re concerned about filling, and The Rules are a selfless way of living and handling a relationship.” The reader is left wondering when she could finally let her — long! only long! — hair down and be her pushy, needy, authentic self. (Answer: Never. A subsequent book was The Rules for Marriage.)

But what The Rules offered, more than anything, was a strategy. I was certain, at the age of 26, that my failure to secure a boyfriend meant I was doing something wrong. I was an only child, raised by an eccentric single mother who longed for a more conventional family. I fetishized traditional marriage, and I was sure other women knew something about men I didn’t know. Those of us baffled by the opposite sex eagerly reached for the map to happiness that The Rules promised. Four hundred years ago we might have paid a witch for a love potion; in the 1990s we paid Fein and Schneider $6 for what amounted to a personal marketing plan.

So I decided to try The Rules on Brian, the vintage-store guy, in the hopes that my three-dates-then-crickets streak could be broken. I hoped The Rules, however flawed, would offer a scaffold upon which to build a romance.

My failed experiment with The Rules

Rule No. 7, “Never Accept a Date for a Saturday Night if He Asks After Wednesday,” was the first test. Brian called on Friday to ask me out for the next day, which I declined, and so I spent an irritable, lonely Saturday night eating Thai takeout and watching a Blockbuster movie. (It dimly occurred to me that I had deliberately deprived myself of a potentially fun evening in favor of solitary moping, but I pushed that thought aside.) The Rules, if followed correctly, sometimes meant you spent a Saturday night alone, losing the battle to win the war, so to speak. Your full social calendar — even if it was a pack of lies — inflated your value in a potential mate’s eyes.

We made a date for the following weekend. I spent that week in a fever of anticipation. Per Rule No. 1 (“Be a Creature Unlike Any Other!”), I groomed myself to buffed, plucked perfection.

He, when he picked me up (Rule No. 4: “Don’t Meet Him Halfway) was in work pants and a stained T-shirt. We went to an improv comedy show, the Upright Citizens Brigade.

“I need a word from the audience,” said one of the comics.

“Vagina!” someone called out.

I started. It was Brian, right beside me. He laughed, a Beavis and Butthead heh-heh-heh. “Vagina!” he hollered again. “Va-gin-UH!” he screamed, as the comic lifted his eyebrows and I shrank in my seat.

“Refrigerator,” said someone in the audience.

“Refrigerator it is,” said the comic, and the show started.

I put it out of my mind — he was probably nervous.

The next week, I again waited for him to call (Rule No. 5: Don’t Call Him, and Rarely Return His Calls”), and when he did I offered no input about what I wanted to do on our date (“He picks most of the movies, the restaurants and concerts the two of you go to”). He chose a dank, deserted diner along the Brooklyn-Queens Expressway with 900 menu items and a clientele straight out of a William S. Burroughs novel. “Another glass of chardonnay, why not!” I said cheerfully to the waitress, per Rule No. 9: “Be Sweet and Light.”

“I got to AA every day,” he said. “Every single day for 13 years.”

“But — you’re only 30,” I said.

“People can be serious alcoholics by 17, Leigh,” he said severely.

Then he chuckled. “Plus that’s pretty much how I meet women.”

I still hoped, after three terrible dates, that we were inching toward the kind of intimacy I longed for

I brushed this aside and pressed on with The Rules. I asked about his work, even though he didn’t ask about mine. “Where do you get the stuff for your shop?” I asked.

He said he paid the Salvation Army drivers to swing by his store before they took their loads back to headquarters.

“So —” I said, valiantly hanging on to sweet and light. “Basically, skimming from the Salvation Army?”

He chuckled, heh-heh-heh.

So, yes, technically, The Rules were working so far, even though I was batting down a niggling feeling that he might be a jerk. I resolved to give it one more chance.

On our third date, a potentially important one (Rule No. 15: “Don’t Rush Into Sex” and “No More Than Casual Kissing on the First and Second Dates”), he took me to a house he was renovating in Red Hook, a waterfront neighborhood in Brooklyn. He wanted to tear out the concrete backyard, so he directed me to stay inside the abandoned house, alone, with his dog. I sat on a milk crate on the dusty floor as he spent the evening whacking a sledgehammer against solid pavement.

I petted his dog in the dark house and listened to him smash and grunt. I debated going out to talk to him, but decided against it. (Per Rule No. 3: “Most men find chatty women annoying.”)

After an hour, I pulled down the tiny arm of my first cellphone and called my mother. No slouch at fixing up houses herself, she said, “He’s banging at a concrete pad with a sledgehammer? There are tools you can rent to tear that out.” She paused. “This is a date?”

“He’s crying now,” I whispered. “Just banging the concrete and crying.”

“I think you should go home,” she said. “Can you call a taxi?”

I hung up with my mom (Rule No. 6, “Always End Phone Calls First”) and listened to my beau weep in the backyard.

This is incredible to me now, but I didn’t take a cab home. I went with him to his apartment. Despite his behavior, he felt familiar to me in a way that New York men didn’t. He fit into the context of my eccentric, artist, country upbringing — my grandmother brought her own Scotch to restaurants and yelled at waiters if they objected; my mother once accidentally painted an outhouse lavender; my stepfather shot our car. I knew from weird. I still hoped, after three terrible dates, that we were inching toward the kind of intimacy I longed for — not necessarily a sexual intimacy, but the sort where you help yourself from someone’s kitchen and go to Lowe’s for cabinet pulls and sometimes take the dog for a walk. I wanted to be a girlfriend.

That lasted about one minute longer.

Why not? Sherrie Schneider and Ellen Fein, authors of The Rules, pose with a bunch of wedding dresses. (Evan Kafka/Getty Images)

Just as we walked in the door, he said, “I don’t do latex.”

We stood in silence for a moment. “You know,” I said in the lighthearted voice all women use when they’ve decided to flee but don’t want to tip their hand. “I’m really tired, so I think I’m going to head home now.”

“Why?” he said, and raised his hands, still filthy from the sledgehammer. He frowned — his previously attractive face now rather ferret-like.

“Oh, just, you know, beat,” I said, and dialed a taxi service.

“One minute,” the dispatcher barked, and I grabbed my coat.

“So,” I lied cheerily, “let’s talk next week —”

He followed me down the hall and grabbed my arm as I pressed the button for the elevator.

“Hey!” I said, startled, and pulled away.

“Look, if you leave now,” he said, grabbing my arm again, “it’s over.” He pushed his face into mine as we stepped sideways into the elevator.

“That’s fine,” I said, abandoning the lighthearted voice and shaking him off again.

“Do you understand that if you leave now, it’s over?” he shouted, as he followed me out of the lobby and onto the sidewalk to the waiting car.

“I totally and completely understand that,” I said, and slammed the car door behind me. (Rule No. 11, “Always End the Date First.”)

The taxi took off down the street and he ran after it, screaming, “This is your last chance — do you get that? It’s over if you get in that car!”

“I am already in the fucking car,” I screamed out the window as the driver turned onto Atlantic Avenue and sped up to catch the light.

I wish I could say doing the Rules on Brian taught me an immediate and tidy feminist lesson. But personal change moves at a glacial pace. My experience with Brian was only the first tiny inkling that what I really needed to do was stop dating losers. In the intervening years between then and when I my met my (non-loser) husband, I unfortunately had to learn this lesson over and over again: You Are Better Than a Lot of the Men Who Ask You Out.

20 years later, dating norms haven’t changed much. Why?

Criticism of The Rules was primarily directed at women — that it encouraged women to play games, that it made women manipulative. But in a patriarchy, it’s rational to divine the needs of the powerful, to meet them, and to be chosen to share their position in the world. Historically, women haven’t had a lot of agency in selecting a mate, and that history, however muted now, still influences contemporary courtship. The Rules proposes to correct that lack of agency by taking away even more of your agency. It could be subtitled Strategies for Chattel.

Women still don’t have a ton of agency in early courtship.

In 2014, Ellen Lamont, a sociologist now at Appalachian State University, published two studies of heterosexual dating rituals among young men and women living in the Bay Area. She found that though most of this group identified as progressive and even feminist, those who cited marriage and children as a goal nonetheless stuck to traditional scripts while dating. “[T]he message from The Rules was definitely brought up frequently by the women I interviewed,” said Dr. Lamont in an email. “Women worry about appearing too desperate should they decide to pursue a man, and they worry this judgment will come from both men and other women.”

She stresses that women were, however, “quite active” in securing dates — they would arrange to run into a man they were interested in at a party, for example. They just weren’t asking the men out or paying for the dates. The women believed men naturally want to be the pursuers — as The Rules says — and they were willing to accommodate that and even construct a narrative that hid their own behind-the-scenes orchestrations.

But most of the men claimed that, actually, they didn’t like these gender norms in dating. They wanted women to ask them out; they wanted women to pick up the check. So why the disconnect? Well, because in practice, it didn’t work: Dr. Lamont’s female subjects said their experiments in being forward usually didn’t get them the outcome they wanted.

I wish I could say doing The Rules taught me an immediate and tidy feminist lesson

Kathleen Bogle, a professor at La Salle University, found in researching her 2008 book Hooking Up that sexually aggressive college-age women were “sanctioned” for their behavior: they faced a certain amount of judgment from their peers in the form of a bad reputation. In her later interviews with post-college men and women, Dr. Bogle found, as Dr. Lamont did, that the fear of appearing “desperate” kept women from taking the overt lead in dating.

I asked Dr. Bogle whether this is a case of men not actually knowing what they want and women deciding it for them? Not exactly, she said. “Sociologists think of gender as a performance. It’s something you act, something you demonstrate for other people.” We’ve “performed” our gender for so long, and the role is so ingrained, that it affects how we feel about ourselves and other people. Men can say, “I’d like women to do the asking and the paying,” but nonetheless the moment she reaches for the check feels awkward, for both the man and the woman.

“An analogous situation,” says Bogle, “is that men say they’d love it if their wives made more money than them. But when that actually happens, it causes problems. The men feel emasculated; their friends tease them. The women, as Arlie Hochschild showed in The Second Shift, then do even more housework and child care to compensate for the men’s feelings.”

Dr. Lamont found in her research that traditional gender roles in dating — which both men and women participated in and enforced — continue in marriage. And perhaps more important, these unspoken roles have a way of accruing privilege to the men in terms of housework and child care. Dr. Lamont found, as Dr. Bogle had, that the unequal division of household labor was also framed as personal preference: “Cooking is her hobby,” the men would say. “Or doing dishes is her thing. My thing is … sitting on the couch, not doing dishes.” Dr. Lamont said, “[Early on], a man might show care by paying for something, while a woman might show care by making a nice meal. As the relationship turns more serious, woman’s care work looks an awful lot like housework, while men usually continue to make isolated romantic gestures as signs of their care for the partner.”

The Rules emphasizes that men are naturally, biologically wired to be the pursuers, and women ignore that at their peril. So women adjust their behavior to conform to what they believe men want, even when it means — as in my case with Brian — that they squash their own needs and desires. “Men Do What They Want to Do,” intones The Rules, like that’s an immutable fact that must be accommodated.

It’s possible that as women gain economic and political power, dating will change, too. But it hasn’t happened yet: The Rules is still in bookstores; the salesperson at Barnes & Noble grabbed it for me before I even said the whole title. Several women in Lamont’s 2014 study explicitly mentioned it. A search for newer dating guides on Amazon shows titles with some variation on “make yourself irresistible” for the books marketed to women.

The men’s contain active verbs, like seduce. In fact, the most visible “dating” guide since The Rules has been The Game, a guide for the “pickup artist” community. It has been suggested that The Rules is directly responsible for The Game — if you’re playing games, we will, too — but I’d argue that the pickup artists are actually responding to women’s growing economic power. The precise moment marginalized groups manage to eke out a little clout is the same moment various dipshits redouble their efforts to wrest back control. The curious thing about The Rules and pickup artists is that they both focus on destabilizing women. If The Rules is a love potion, The Game is a roofie.

But in the meantime, the courtship expectations of The Rules are still here. So is anything ever going to change? “Dating has been this way for a long, long, time, and it’s really hard to break out of these scripts,” said Dr. Bogle. “Regarding feminism, the gains in the workplace have been relatively fast, but women were leading the charge and there was a clear motive and benefit.”

Changing the norms around romantic relationships isn’t going to be as simple, according to Bogle, in part because it’s not clear who would instigate the change.

“Who’s going to lead the charge on dating? The men who don’t want to pay? The women who want to pay? I don’t see it happening anytime soon.”