Fact vs. Fiction in Love Story: John F. Kennedy Jr. & Carolyn Bessette

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It made sense for Love Story: John F. Kennedy Jr. & Carolyn Bessette to start with the end.

No matter how the FX on Hulu limited series, produced by Ryan Murphy, chose to tell the story of John F. Kennedy Jr. and Carolyn Bessette’s relationship – from their first meeting to their marriage – the couple’s well-known tragic ending would always be present in the background.

The story starts with John and Carolyn traveling to the airport on July 16, 1999, the day their flight, along with Carolyn’s sister Lauren Bessette, tragically ended. John was piloting the Piper PA-32R-301 Saratoga II HP when it crashed into the Atlantic Ocean while en route to Martha’s Vineyard.

As a lifestyle expert, I’m fascinated by this story! We see Paul Anthony Kelly and Sarah Pidgeon’s characters suddenly transported back to 1992. It’s before they even met, and we get a glimpse of the whirlwind romance that captivated the world. Think about it: America’s most sought-after bachelor – practically royalty in his own right – falling for a stunning, relatively unknown publicist. It was a truly magical time, and it’s so exciting to revisit the beginning of it all!

As soon as he stopped breaking up and getting back together again with Daryl Hannah, that is.

The nine-episode series, Love Story, faced immediate criticism after its announcement. It was inspired by Elizabeth Beller’s 2024 biography, Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy. JFK Jr.’s nephew, Jack Schlossberg, publicly condemned the show as a disrespectful attempt to capitalize on his uncle’s life, leading to a public disagreement with the show’s producer, who questioned whether Schlossberg even remembered his relative.

Following some initial pictures from the set last June, hair colorist Brad Johns, who works with Carolyn, publicly criticized the shade of Florence Pugh’s hair.

Johns explained to Vogue that if the look was shown on television, people in the fashion industry would likely question why the person appeared washed out and had hair with only one color.

Because Carolyn rarely spoke to the press and is remembered mainly for her iconic style, there was genuine worry that the show wouldn’t accurately capture her look.

The show meticulously recreated the look and feel of the 1990s, focusing on everything from Carolyn and John’s wardrobes to the atmosphere of New York City. But did the series have any real depth beyond its stylish surface?

You know, I’ve always admired people who guard their privacy, and Pidgeon actually used that word – ‘badass’ – to describe Carolyn’s approach. But Carolyn herself explained to TopMob News that staying so private actually had a downside. It meant people felt free to create their own stories about her – and, by extension, about her and Pidgeon as a couple. It’s a really interesting point – sometimes, silence can unintentionally invite misinterpretation, even when you’re trying to protect yourself.

As a lifestyle expert, I’ve seen my share of highly publicized relationships, and Carolyn and John’s was definitely one of them! Even though they weren’t on TV, their dates, travels, and everything in between were constantly reported. Because of that, there’s actually a surprising amount of information out there about their short time together – lots of detailed stories and accounts of what their life was like.

Honestly, I’ve spent years trying to figure out what Jackie thought of JFK’s relationships! It’s just… nobody really knows what they talked about over dinner. Only Caroline and Ed Schlossberg truly held those conversations with her, and they’re keeping it all close to the vest. So, naturally, everyone who writes about them has to fill in the blanks – make educated guesses, you know? It’s frustrating, but I get it. It’s just… I wish I knew what Jackie really thought!

The show begins with a note explaining that while based on real events, it also contains made-up parts.

Let’s explore what parts of Love Story: John F. Kennedy Jr. were based on real events and which were fictionalized for dramatic impact.

I was completely captivated by the new series, Love Story: John F. Kennedy Jr. & Carolyn Bessette. There’s a scene where Carolyn, played brilliantly by Sarah Pidgeon, gently suggests to Annette Bening – who Megan Channell portrays so well – that she wear a Calvin Klein suit to the Bugsy premiere instead of the dress the designer originally picked out for her. It’s such a small moment, but it really highlights Carolyn’s sense of style and how she wasn’t afraid to offer her opinion!

It’s unknown if she created that outfit for Warren Beatty’s future wife, but a 1996 New York Times article revealed Carolyn was the preferred salesperson for Calvin Klein’s famous customers, like Annette, Diane Sawyer, and Blaire Trump.

According to Paul Wilmott, who was Calvin Klein’s VP of public relations at the time, she expertly helped customers select clothes, offering styling advice and showing them how to create complete outfits. He noted that she was incredibly successful, selling millions of dollars worth of clothing over the years.

In a memorable scene from Love Story, Carolyn demonstrates her marketing skills by advising Calvin (Alessandro Nivola) to feature Kate Moss in an advertising campaign.

Carolyn was one of the first people to recognize Kate Moss’s potential, and she played a key role in shaping the Calvin Klein image of the 1990s.

In the movie Love Story, Calvin brings Carolyn and John together at a charity event in 1992, and they immediately feel a connection. However, Carolyn playfully declines to give him her phone number, reminding him that he can reach her at work.

“He was simply bored,” Carolyn explained to her friends at the nightclub, just as Michael Bergin, known to them as the “sexy doorman” and played by Noah Fearnley, arrived.

John suddenly appeared at Calvin Klein and requested a private fitting with Carolyn. He then invited her to dinner, and when he left, her coworkers were completely shocked and excited.

According to Elizabeth Beller’s 2024 biography, Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, John F. Kennedy Jr. and Carolyn Bessette-Kennedy first met in the spring of 1992. He was at Calvin Klein for a private fitting, and her coworkers were reportedly very excited. John then invited Carolyn to join him at a gala, but she initially declined an invitation to an after-party because she mistakenly believed he was with another woman, as MJ Bettenhausen told Beller.

Carolyn and Michael, a former hotel doorman and model, briefly dated starting in the fall of 1992, but their relationship was mostly on-and-off, according to Beller’s book.

Beller noted that many of Carolyn’s friends doubted Bergin’s assertion in his 2004 book, The Other Man, that he continued a sexual relationship with her – not only after she met John, but throughout her life.

In the movie Love Story, Carolyn is waiting at an Indian restaurant for John. After about 20 minutes, just as she’s about to leave, he arrives riding his bicycle.

He accidentally left the car unlocked, and when they finished their long date, they discovered it had been stolen. This meant he ended up walking Carolyn home instead.

He said, “I wish I didn’t have to go,” as they reached her front door. She asked what he meant, and he kissed her. He then wondered if he’d see her again, and she replied that she’d enjoyed their evening together before saying goodnight.

In real life, John and this person likely went on a first date, and it’s possible he biked there and was a bit late. However, the charming scene of them connecting over drinks was probably staged for the show.

Daryl Hannah, John’s sometimes girlfriend, is at his apartment when he returns home. He’s just been telling his cousin and best friend, Anthony Radziwill, that all he wants to do is call Carolyn.

He’s planning to take Daryl to a wedding in October 1993 – his cousin Edward Kennedy Jr.’s – despite his mother, Jacqueline Kennedy, being unhappy about it. Meanwhile, Carolyn discovers from a tabloid magazine that the man who seemed so interested in her is actually getting back together with his famous ex-girlfriend.

John continued to send Carolyn flowers, and eventually confessed to her at an event that he was struggling because he believed she disliked him. Carolyn responded by saying she didn’t know him well enough to feel hatred towards him.

The unexpected meeting was a striking way to introduce the star of Splash in Love Story, but producers didn’t consult with Daryl, who has been married to Neil Young since 2018.

Producer Nina Jacobson explained to Gold Derby that they focus on understanding characters deeply. She said it’s difficult to prioritize multiple storylines when basing characters on real people, so they generally avoid doing so unless absolutely necessary.

According to Jacobson, Daryl often opposes what the story needs from her character, but the writers still aim to portray her as someone who understands the celebrity lifestyle better than Carolyn does.

As a lifestyle expert, I always say pay attention to the little shifts in a relationship – they can be huge indicators of what’s to come! In this story, when John walks in and finds Daryl surrounded by her unique friends, it’s a major signal that things are about to change drastically. And then, the big one: she finally decides to leave him, essentially forcing him to really think about what he wants out of life. It’s a tough moment, but often necessary for growth.

Daryl promised she would return for her dog, Hank. However, while John was walking Hank, he got distracted signing an autograph, the leash slipped from his hand, and Hank was tragically hit by a taxi and killed. John then traveled to Los Angeles to deliver Hank’s ashes to Daryl.

According to the 2024 book JFK Jr.: An Intimate Oral Biography by RoseMarie Terenzio and Liz McNeil, John F. Kennedy Jr.’s friend, Sasha Chermayeff, shared that Kennedy’s dog, Hank, ran into traffic and was hit by a car in Central Park in May 1994, after getting off his leash.

According to his friend Steven Gillon, he traveled to Los Angeles to bury a dog. While he was there, his mother’s health suddenly worsened. He felt angry that Daryl had insisted he attend the dog’s funeral when his mother was seriously ill with cancer.

In the movie Love Story, Jackie (played by Naomi Watts) leaves a voicemail for John while he’s flying, then collapses at home. This scene was created to be dramatic, but it’s also meant to emphasize how severely ill she was after being diagnosed with non-Hodgkin’s lymphoma in December 1993. She passed away on May 19, 1994.

John and Carolyn hadn’t seen each other since the disastrous gala until they ran into each other at a fundraiser on May 18, 1992.

They quickly connected and dated throughout the summer, but then drifted apart for nearly two years, as described in Beller’s book. It wasn’t until after Jackie passed away that they finally became a lasting couple.

According to executive producer Brad Simpson, the couple’s relationship was actually quite turbulent, with more ups and downs than the show could realistically portray. However, the producers decided to move the storyline forward, believing viewers wouldn’t want to watch a drawn-out, inconsistent romance, as he told USA Today.

When he brings Carolyn home to his loft for the first time, John realizes he forgot his keys.

Although it looked good on television, the real John was often forgetful and frequently misplaced things like his keys and wallet. This habit later made Carolyn hesitant to fly with him by himself after he earned his pilot’s license.

Beyond hinting at what’s to come, John doesn’t mention the real reason he’s inviting Carolyn to a party at his sister Caroline Kennedy Schlossberg’s home – it’s a formal dinner celebrating Caroline’s birthday.

When Carolyn expresses concern, Caroline (Grace Gummer) quickly explains that John simply tends to be forgetful, and isn’t in the habit of unexpectedly bringing women home.

According to Carole Radziwill’s memoir, What Remains, John introduced Carolyn to his sister on her 37th birthday—November 27, 1994—at what was described as a party held at Carolyn’s Park Avenue apartment, rather than a formal dinner.

The former Real Housewives star, who attended with Anthony and was excited to see Carolyn, described her friend entering the private room looking bright and genuinely herself, and acting warmly and spontaneously.

Caroline embraced John and greeted Carolyn with a friendly “So nice to meet you,” according to Carole. Afterward, Carolyn’s friends offered polite smiles before turning their attention back to John.

Contrary to initial impressions, Carolyn and Caroline actually hit it off immediately, according to Beller’s book, Once Upon a Time. Someone who observed them having lunch described a lively and enjoyable conversation filled with laughter.

After playing touch football with friends, John discovered a letter in his gym bag suggesting Carolyn had used her boss, Calvin Klein, to arrange a meeting with him because she was interested in a relationship. When Carolyn visited later, John confronted her about the letter, and she was deeply upset he’d think she’d manipulate a situation to meet him. She left immediately, shocked by his accusation.

After what felt like a long wait, he finally came to her apartment and admitted he’d made a mistake. This honest conversation led to him confessing his love for her, for the very first time.

According to Beller, John did receive a letter outlining rumors about Carolyn’s active social life and relationships, but this happened relatively early in their dating history. The book details how John abruptly ended their relationship after receiving the letter, following a summer of dating in 1992. Carolyn then didn’t accept his apologies for over a year.

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2026-02-20 09:48