Like many others, I’ve been captivated by FX’s Love Story: John F. Kennedy Jr. and Carolyn Bessette. It’s not because I’m nostalgic for Camelot or have vivid memories of New York City in the ’90s—much like Jenna Maroney from 30 Rock, my recollections are faint due to age—but because Sarah Pidgeon’s portrayal of Carolyn as a cool, cigarette-smoking icon is irresistible, even though the media eventually drained her vitality.
In the fourth episode of Love Story, while avoiding calls from John F. Kennedy Jr. (played by the striking Paul Anthony Kelly), her friend Narciso Rodriguez teasingly asks, “Screening his calls. What, did you read that in The Rules or something?” This reference to Carolyn’s tactic of “Exploit his insecurities” piqued my interest, leading me to revisit the 1995 book The Rules: Time-tested Secrets for Capturing the Heart of Mr. Right by Ellen Fein and Sherrie Schneider, which offers a step-by-step guide to achieving heterosexual romance. Now that I’m single and cautiously exploring my bisexuality, I thought it was time to see if this book’s advice holds up in the era of app dating. Fein and Schneider’s early 2000s follow-up, The Rules for Online Dating: Capturing the Heart of Mr. Right in Cyberspace, seemed less relevant.
It’s worth noting that even in the mid-’90s, The Rules might have been questionable and certainly weren’t feminist. Fein and Schneider advise women to avoid initiating conversations with men, avoid staring or talking to them too much, not to call or return calls frequently, and to delay intimacy. Having spent a decade exploring queer relationships and a four-year-long relationship, I decided to test The Rules over the past week.
As a dedicated journalist, I ventured out on a Hinge date on Sunday night, following my coverage of the 2026 Oscars. It was my first date with a cisgender, heterosexual man in about a decade.
Though The Rules don’t mention having two glasses of orange wine before meeting a date, I did so for my nerves. When he arrived, I disregarded nearly every guideline from Fein and Schneider. I initiated conversation to avoid awkward silences, offered to buy him a drink, shared personal stories from my childhood, and ignored the rule against more than casual kissing on a first date.
While I won’t divulge all the details, I did invite him back to my apartment—another breach of The Rules. My small, unfriendly dog, a better follower of The Rules than I am, barked at him for 20 minutes, and I served him water in a wine glass. After he left, I felt like a character from a Cathy cartoon, wondering if he liked me and if throwing The Rules aside had ruined the chance of being properly pursued.
