The Rules:

On Becoming Fluent in Myself, and Other Lessons in Midlife Dating

The other day I found a stray box of books that had been shoved into the back of a closet, overlooked since my move last summer. Inside was a collection of yellowed, dog-eared paperbacks I’d toted around from house to house over the years, like old friends I was never quite ready to part with. What surprised me wasn’t that I’d kept them. It was what I found tucked between well-worn copies of To Kill a Mockingbird and The Great Gatsby: The Rules: Time-Tested Secrets for Capturing the Heart of Mr. Right.

Now there’s a blast from the past.

If you were dating in the mid-90s, chances are you remember it. It wasn’t just another dating book. For a brief (and, in hindsight, spectacularly unhealthy) moment in time, it was a dating bible, passed from friend to friend over glasses of cheap wine while we debated whether Ross and Rachel were really on a break. Follow these rules, it promised, and you would find lasting love.

Curious how it might read through my now single fifty-three-year-old eyes, I sat down on the couch and started turning pages.

Here are a few gems:

Don’t talk to a man first.

Let him take the lead.

Don’t call him.

Rarely return his calls.

At first, I laughed. I laughed because it felt so impossibly outdated, like discovering an old etiquette manual warning women not to show their ankles in public. It was hard to imagine that any of us had once taken these rules so seriously. But the I sat with it, the less funny it became.

Because…of course, we did.

Those rules didn’t appear out of thin air. They reflected the culture we were raised in and the messages we’d been absorbing since we were girls. Be accommodating, but never needy. Independent, but never intimidating. Attractive, but not too available. Interesting, but never so opinionated that we risked making someone uncomfortable. Above all, we learned to wait to be chosen.

Looking back now, I don’t think The Rules taught us anything entirely new. They simply gave language to beliefs many of us had already internalized. They reinforced the idea that love wasn’t something we trusted to unfold honestly. It was something we earned by carefully managing how much of ourselves we revealed—and when.

Fast forward three decades, and the girl who grew up absorbing all of those messages suddenly finds herself back in the dating world, trying to make sense of it all over again.

To be fair, this won’t actually be my first venture into online dating after my divorce. A few years ago, I dipped a tentative toe into those waters and found myself in a relationship that lasted nearly two years. Like so many relationships, it began with hope and possibility and ended in heartbreak. It took me a long time to find my footing again. To trust myself again. To believe that opening my heart hadn’t been a mistake, even if it hadn’t lasted.

Now, for the first time in quite a while, I feel ready to give it another go. But if I’m honest, there’s something even scarier about returning after you’ve been hurt. The first time, I didn’t know what to expect. This time, I do. And that’s both the challenge…and, perhaps, the gift.

Apparently, while I was busy healing, dating evolved into something that occasionally feels less like romance and more like being dropped into a full immersion foreign exchange program. No phrasebook. No translator. Just smile politely, do your best, and hope you don’t accidentally agree to something you didn’t mean to. Somewhere along the way, people stopped simply breaking up and started ghosting, breadcrumbing, catfishing, benching, orbiting, and entering situationships. Ethical non-monogamy became a thing. So did polyamory. There are green flags, red flags, beige flags, and enough new terminology that I feel like and enough new terminology that I feel like everyone should receive a glossary the moment they download a dating app.

The technology has changed. The vocabulary has changed. The expectations have changed. We no longer wait by the family phone wondering if he’ll call before seven. Instead, we analyze text messages, debate the appropriate amount of time to wait before responding, wonder why someone viewed our social media posts but never replied, and somehow convince ourselves that all of this is perfectly normal.

But here’s what hit me the hardest. The rules may have changed, but something underneath them feels remarkably familiar. It still feels like a game. And that’s the part I struggle with most.

After everything life has taught me over the past thirty years—after a marriage, motherhood, heartbreak, grief, therapy, reinvention, and more self-reflection than I ever imagined possible—I find myself wondering why dating still seems to require strategy. Why does it still feel as though we’re trying to solve some elaborate puzzle instead of simply getting to know another human being? At what point do we get to stop performing and just be ourselves? Because the woman considering dating today bears very little resemblance to the young woman who first devoured The Rules.

Back then, I was looking for someone to build a life with. I was thinking about marriage and children and buying a house and all of the milestones that seemed to define adulthood.

Today, I already have those things. I’ve built a life I genuinely love. I have friendships that sustain me, work that gives me purpose, a city that feels like home, and a little apartment that represents one of the bravest decisions I’ve ever made. I’m not looking for someone to rescue me from loneliness or complete a picture that feels unfinished.

I’m looking for someone who has put down a few roots of his own. Someone who knows who he is. Someone who has survived a few hard seasons and learned from them. Someone curious enough to keep growing and secure enough to let another person be fully herself.

Maybe that’s why rereading The Rules felt so jarring. Not because the advice was outdated, but because I no longer recognized the woman those rules were written for. The hardest rule to break was never about who calls first or how long to wait before returning a text. It was the one that taught so many of us that love depended on becoming whoever someone else was hoping to find.

I spent years trying to learn the language of being chosen. Midlife taught me the language of becoming. This time, I’m not looking for someone to choose me. I’m looking for someone who recognizes the woman I’ve already chosen to become.

Rules be damned.

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