Like pretty much everyone else, I’ve been captivated by FX’s Love Story: John F. Kennedy Jr. and Carolyn Bessette. It’s not that I buy into the whole Camelot myth, or even remember the ’90s in New York (in my best Jenna Maroney from 30 Rock voice: I was too young!). It’s more that I can’t tear my eyes away from the gorgeously elusive, cigarette-smoking, cool-girl version of femininity that Sarah Pidgeon brings to Carolyn—at least until the press starts draining her spirit, but I’m getting off track.

In the fourth episode, as Carolyn dodges calls from John F. Kennedy Jr. (played by the distractingly handsome Paul Anthony Kelly), her friend Narciso Rodriguez teases, “Screening his calls. What, did you read that in The Rules or something?” That hint—that there might be some method behind Carolyn’s “Exploit his insecurities” mantra—piqued my interest. Before I knew it, I was diving into the lore of 1995’s The Rules: Time-tested Secrets for Capturing the Heart of Mr. Right, Ellen Fein and Sherrie Schneider’s step-by-step guide to landing heterosexual love. Now that I’m single and somewhat reluctantly exploring my theoretical bisexuality, it felt like the perfect time to see if the book still held any practical advice in the age of dating apps. (Fein and Schneider’s early-2000s follow-up, The Rules for Online Dating, held far less appeal for me, with no Carolyn Bessette connection to speak of.)

To be honest, I’m not sure The Rules ever made much sense, even in the mid-’90s, and they certainly weren’t feminist. Among other things, Fein and Schneider advise readers not to speak to a man first, not to stare at men, not to talk too much, not to call them or return their calls promptly, and, of course, not to rush into intimacy. But after a decade in queer circles and a four-year relationship, I was ready to embrace being “a creature unlike any other.” So this past week, I decided to put The Rules to the test.

As a committed journalist, I dutifully dragged myself out on a Hinge date Sunday night (after covering the 2026 Oscars, no less—where’s my Pulitzer?). And this wasn’t just any date; it was my first with a cisgender, heterosexual man in about ten years.

The Rules says nothing about downing two glasses of orange wine at the bar before your date arrives, so I obviously did that to calm my nerves. Then, when he showed up, I proceeded to break almost every rule in the book: I talked first (I hate awkward silences!), I didn’t go Dutch (I reflexively offered to buy him a beer when I went for my third wine, and he accepted!), I probably overshared (I think I talked a lot about my childhood?), and, of course, I committed the cardinal sin: more than casual kissing on the first date.

I’m too much of a lady to go into detail, but let’s just say I ended the date (and not first—another Rules no-no) by inviting him back to my apartment. There, my tiny, feisty dog—who’s clearly a better Rules follower than I am—barked at him for a solid 20 minutes, and I served him water in a wine glass like the domestic goddess I am. The moment he left, I morphed into a Cathy cartoon. Did he like me? Would I see him again? Had I ruined any chance of being properly pursued by tossing The Rules aside, despite my best intentions?

The next day, I met up with my slightly older, much wiser, also-bisexual friend Sarah at the Marquis Sunset pool. Drawing from her own recent experience dating cishet men, she offered some guidance: “If you want to sleep with them, sleep with them. But my rule is, if you want so much as a text in the morning, you should delay that as long as pUnlike the authors of “The Rules,” Sarah emphasized that this was far from a requirement. No one actually needs a “How did you sleep?” text from a guy, and honestly, if I didn’t get one, it would just free me to keep moving forward in my dating life.

Encouraged by Sarah’s outlook, I skimmed my copy of The Rules again by the pool, searching for even one rule I could fully stand behind. Finally, I found it: “Fill up your time.” Well, technically the full rule is “Fill up your time before the date,” and I didn’t have a second date planned. But I figured if CBK could eventually answer the phone and marry John-John, I could tweak a dating rule written when I was two years old to fit my 2026 life. I’d just focus on being too busy to worry about whether a guy texted first, replied, or watched my Instagram Stories.

With that mindset, I booked a Pilates class and made plans for drinks with friends, aiming to stay occupied enough not to check my phone all day—and guess what? He did text back. Was it a little generic? Sure. Did it include a solid plan to meet up again? Not exactly… but so what? I did hear from him. Cheers to breaking the rules, girls!

Frequently Asked Questions
Of course Here is a list of FAQs about revisiting the 1995 dating guide The Rules in the modern dating app era

Beginner Definition Questions

1 What were The Rules anyway
The Rules was a bestselling 1995 dating guide that advised women to follow strict traditional protocols to land a husband Key rules included Dont talk to a man first dont ask him out always end phone calls first dont see him more than twice a week and dont have sex before marriage

2 Is this book still relevant today
Its core philosophy of playing hardtoget is debated While some principles about selfworth and boundaries are timeless the specific rigid tactics feel outdated in an era of gender equality and direct communication via apps

3 Who wrote it and what was the main idea
Ellen Fein and Sherrie Schneider wrote it The main idea was that by being a Rules Girl a woman could inspire a mans pursuit and commitment framing dating as a strategic game with the goal of marriage

Modern Application App Culture Questions

4 Can you follow The Rules on dating apps like Hinge or Bumble
Its challenging On Bumble women have to message first breaking Rule 1 The general advice would be dont doubletext dont be overly available in chat and let the man ask for the date and plan it The spirit of dont chase is adapted not the letter

5 How does The Rules approach conflict with modern dating norms
Modern dating emphasizes authenticity open communication and shared effort The Rules advocated for scripted behavior withholding affection and letting the man lead entirely which can feel manipulative or passiveaggressive today

6 Whats a Rules principle that actually still works well
The emphasis on having a full independent life is more relevant than ever Being busy confident and not centering your world around a new match is healthy and attractive on or off apps

7 Whats the biggest problem with applying The Rules now
It assumes a linear dating path and doesnt account for modern complexities