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The Obsession with JFK Jr. and Carolyn Bessette Haunts Us All

  • Writer: Neha Ogale
    Neha Ogale
  • 7 hours ago
  • 8 min read

Thanks to Love Story, men and women alike are biking around the city, dyeing their hair platinum, and scavenging for vintage Calvin Klein. But how long can we play pretend?



“Please don’t get so close to me.”


Carolyn Bessette never gave a single interview. Fewer than 100 photographs of her are in the public domain, and even fewer of her audio clips. Rare footage reveals, in just seven words, that she had a voice and certainly wasn’t afraid to use it when necessary — oval sunnies and tortoiseshell headband in place. 


The first-season release of Ryan Murphy’s FX anthology series Love Story has prompted a whole new generation to rediscover the 1990s It Girl, whose high-profile romance with John F. Kennedy Jr. captured the public imagination in a way few, if any, other couples have. America’s Prince has found his princess, the tabloids crooned. Only the much-anticipated engagement of then-Lady Diana Spencer to Prince Charles and the ensuing public frenzy could rival that of these American royals, though the gap in their individual appeal was only too obvious. 


“Diana didn’t just upstage Charles,” commented Tina Brown, former Vanity Fair editor-in-chief and author of The Diana Chronicles, for a 6-part CNN docuseries on the British Royal family. “She eclipsed him, actually,” adding, wry as ever, “I mean, she made him nothing, is the truth.” 


The “golden couple” of the ‘90s, though, were glamorous and disarmingly evocative in their own right, each a star in its own firmament. Murphy’s show, filmed largely on location, has sent waves of tourists flocking to Manhattan restaurants and other businesses of which John and Carolyn were reportedly patrons, perhaps hoping to catch a glimpse of what their life together might have looked like. America’s uncrowned prince and princess have undoubtedly been imprinted on the cultural consciousness. The question that nobody seems to be asking, among the style guides and tourist traps, is: Why? 


Well, why do famous people enjoy enduring popularity decades after their deaths? Looks and money come to mind, certainly. Good posture and immaculate tailoring probably help. As does that awful cliché of a word, charisma. John and Carolyn possessed all of these attributes. But attractive couples have surely lived and died long before their time; as far as I’m aware, we aren’t still producing movies and television shows about them decades later, or trying (and failing) to emulate their very essence. Just last week, hundreds gathered in Washington Square Park for a “JFK Jr. Lookalike Contest.” The men of New York City are nothing if not audacious. 


Of course, an analysis of the unofficial royal couple can’t be done without unpacking the raw magnetism of the Prince’s better half. While John had grown up in front of the cameras, Carolyn was plucked from obscurity and catapulted into the public gaze. Parallels between Carolyn and Princess Diana have inevitably been drawn. Sunita Kumar Nair, author of CBK: Carolyn Bessette-Kennedy: A Life in Fashion and a consultant on Murphy’s show, noted that both women married royalty, either literally or figuratively. 


"Neither…could foresee or empathize with the sheer magnitude of their partner's public status," Kumar Nair told the BBC


Unlike Diana, who openly chronicled her triumphs and struggles, Carolyn was and remains an enigma. How did a girl from the Connecticut suburbs grow up to snag the most eligible bachelor in United States history? Her ascent to New York high society and then into the arms of a Kennedy fueled decades of speculation that have raised more questions than answers. You see, Carolyn had personal lore when having lore actually meant something. If Diana and John understood the power of images and public statements, Carolyn leveraged silence and discretion for the same reasons. In keeping a low profile, she mastered the art of visibility without familiarity, remaining elusive without being cagey. Carolyn was ahead of her time and projected exactly the kind of emotional unavailability en vogue today, though she has been characterized by those close to her as a warm and compassionate figure, much like her husband. Whichever version was her true self, the one facing the cameras understood something her modern-day mimics can’t quite intuit: proximity is often best enjoyed at a distance.  


In keeping a low profile, she mastered the art of visibility without familiarity, remaining elusive without being cagey.

Part of the fascination with John and Carolyn, I think, is also rooted in the serendipitous origins of their doomed romance. If sources are to be believed, their story began in 1992 with a chance meeting in a VIP showroom at Calvin Klein when John came in for a fitting. The premise alone sounds simply implausible today. COVID-19 made pretty much everyone start doing all their shopping online, for one thing, not to mention the steady surge in online dating. By 2022, over 30% of adults under 35 reported meeting their significant other online. Whether John really flagged Carolyn down at work is irrelevant; it’s the thrill of pursuit — of being pursued — that feels anachronistic and therefore so covetable.


The short explanation is that smartphones ruined everything. Rapid technological developments since the turn of the century have fundamentally reshaped social norms, triggering a cascade of downstream effects that promote endless optimization at the expense of genuine lived experience. Think about it: pre-cell phones, pre-social media, walking down the street with headphones on would have been considered terribly antisocial. Third spaces were commonplace, and plans could be made with a quick phone call instead of weeks of lukewarm ping-pong over text. People used to actually talk to their neighbors and engage with members of their community. Now, they can’t even manage the supermarket checkout without their AirPods in. Omniscience and convenience have reduced us to spectators in each other’s lives rather than participants, and, on some level, we have accepted all of this as normal. 


No wonder ‘90s nostalgia is once again all the rage. I would give anything to be able to experience New York City then, even for a day. It just seemed like a simpler time, one where readily available technologies like telephones, computers, and cameras, as well as modern modes of transportation, helped reduce some of the day-to-day load without eliminating the need for intention, effort, or curiosity. I once described the feeling to a friend as a kind of homesickness for a place in time that I never inhabited, at least in any meaningful way. As Gen Xers stumbled through the Meatpacking District (braving the erstwhile slaughterhouses) to hit the clubs, I was probably dodging the umpteeth “two more bites”. Despite the generational gap, I shared at least one quality with those girls: I didn’t know what was going to happen next. That’s all I want, not to know. I want to not know what others are doing every minute of every day. I want to know what it's like to go a whole day without being asked for a username and password. I want to come home to a Panasonic answering machine and listen to my loved ones’ voices on the tapes. John and Carolyn’s story will always resonate because it evokes imagery of what, in retrospect, might just have been the last halcyon days of modern life.


Sarah Pidgeon as Carolyn Bessette Kennedy in Love Story (2026)
Sarah Pidgeon as Carolyn Bessette Kennedy in Love Story (2026)

An identity crisis plagues young adults today. They don’t know what to wear, what to eat, or even what to say without consulting TikTok or ChatGPT. A year ago, on a fine day in the West Village, you could hardly move for white tank tops and sambas. For a demographic with no discernible self-concept yet an ironic desire for main character status, Murphy’s show has reintroduced a brand new protagonist on whom to mold this season’s personality. The Internet did as the Internet does and sent thousands clamoring for “the CBK look,” from her exact shade of blonde to the apothecary reported to have sourced her tortoiseshell headbands, down to the Egyptian musk scent she was rumored to have worn. Men’s publications also seized their opportunity for a quick commission, offering readers a blueprint for achieving John’s “uniquely preppy” style


It wouldn’t be the Internet, though, without rumblings of dissent. Carolyn Bessette-Kennedy Is Not Your Unwitting Brand Ambassador, Allure magazine hissed. Even Cosmopolitan engaged in a bit of finger-wagging: JFK Jr. & Carolyn Bessette Kennedy Don’t Need To Be Your Fashion Icons, a recent Instagram post scolded. What people fail to realize is that their fascination with John and Carolyn is less about the clothes than the context in which the couple wore them. By showing restraint against a backdrop of extravagance, their union represented a higher yet still accessible ideal that the layperson could aspire to, one in which normalcy and simplicity reflected personal values rather than mere branding.   


John and Carolyn's lives have left an indelible mark on contemporary history, yet their deaths are often reduced to footnotes. Mining these figures for content further robs them of their humanity. Perhaps this relentless, wholesale glamorization explains why the reimagining of the couple’s romance could represent yet another welcome if clumsy distraction from the prolonged violence and civic decay flooding viewers’ feeds. To the more skeptical onlooker, though, Love Story is more of a cautionary tale; a dark reminder that the premium we place on youth, beauty, and idiosyncrasy remains lucrative, despite the devastation they leave in their wake, time and time again. 


John and Carolyn continue to haunt us because they were palpably, fallibly, unflinchingly human.

Nearly three decades have elapsed since television cameras recorded Carolyn Bessette telling a ravenous press to back off, and three decades since she and her husband departed on what would be their final journey together — yet the memories linger. Though Love Story takes a fair few creative liberties, we all know how the story ends: John’s ill-advised flight to Martha’s Vineyard, with Carolyn and her sister Lauren on board, cost all three of them their lives when he lost control of the plane and plummeted into the Atlantic. 


“In the US, the Kennedys occupy territory somewhere between the British royal family and Greek tragedy, a tale of impossible glamour pierced by spectacles of public mourning,” writes David Smith in The Guardian. For generations, misfortune and sorrow have haunted one of the 20th century's most illustrious families. Their associates, too, tend to suffer collateral damage. John and Carolyn’s untimely departure from this world seemed to confirm that the so-called “Kennedy curse” had struck once again.


The couple’s relationship was turbulent from the start, and the plane crash occurred at a crossroads in their marriage. Intense public scrutiny, alleged drug use, and murmurs of infidelity on both sides conspired to tarnish their reputation. 


“We must not let in daylight upon magic,” the 19th-century British historian Walter Bagehot once warned. And towards the end, John and Carolyn's spellbinding public image shone in the most lurid light imaginable. By the spring of 1999, numerous outlets had reported that the couple was hurtling toward divorce. The sensationalism of their private lives and the extraordinary circumstances under which they perished proved cataclysmic. Humans can’t help indulge a morbid curiosity about death, and mortality is particularly fascinating when it comes to young people who appear to have it all. Fairytales are supposed to have happy endings. But that’s the thing about fairytales and main characters — they aren’t real. John and Carolyn continue to haunt us because they were palpably, fallibly, unflinchingly human. Through good times and bad, their lives glossed a cultural moment unjaundiced by the trappings of the digital age, spontaneous and brimming with possibility. Therein lies the eternal magic. Their legacy lives on, and that’s why we still care. 🌀



Neha Ogale is a clinical psychology PhD student, relapsed coat hoarder, indie film lover, and occasional writer based in New York City. You can find her on Instagram @urbangremlin.



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