Carolyn Bessette And JFK Jr.'s Marriage Was Plagued By Rumors And Red Flags

Carolyn Bessette and John F. Kennedy Jr.'s relationship was heralded as a love story for the ages. They met in 1992, when Kennedy came into Calvin Klein for a private fitting; Bessette was working in publicity for the brand, and she and Kennedy hit it off. He asked for her number and invited her to a gala with his friends, and the two would go on to have brief, fleeting encounters over the next five years. Things were further complicated by the fact that Kennedy continued to return to Daryl Hannah, his on-again, off-again girlfriend.

When Hannah and Kennedy split for good in 1994, Kennedy pursued Bessette. But she had been hurt by his earlier ambivalence, and so she received his advances with reluctance. "She didn't think [Kennedy] was serious," the couple's friend Gustavo Paredes told People. "He couldn't believe she turned him down. It had never happened before." However, things warmed up, and the two married on September 21, 1996 on Cumberland Island in Georgia. But tragedy hit three years later; on July 16, 1999, they, as well as Bessette's sister Lauren, died in a plane crash off the coast of Martha's Vineyard. The magic of their relationship and their tragic death cast Bessette and Kennedy as having a once-in-a-lifetime love story — and this is certainly the way the 2026 Hulu series "Love Story" pitches it. But the truth is that their relationship was riddled with red flags.

It's no great mystery why John F. Kennedy Jr. proposed to Carolyn Bessette. By all accounts, she was smart and savvy, but also beautiful and could carry herself well in the spotlight. Bessette's chic and simple style remains unmatched, so she was the perfect wife for someone who had been lauded America's most eligible bachelor. Bessette's fashion sense was so distinct that she's solidified herself as a style icon; after all, personal style is timeless, and it can be challenging to find one's own. Bessette's ability to do it so effortlessly made her that much more magnetic.

And while JFK Jr. was no slob himself, Bessette wasn't ready to say "I do" when he proposed. Kennedy popped the question over the July 4th weekend in 1995 while the couple was on a boat off of Martha's Vineyard. Bessette took three weeks to give him a response, essentially giving ladies everywhere a master class in black cat energy. "[Bessette] understood that the formality meant something, especially to John and his lifestyle," author RoseMarie Terenzio wrote in her 2012 book "Fairy Tale Interrupted." Terenzio also noted, "I actually think that made John even more eager to marry her." While Bessette might have been living by slower, more elegant standards, the fact that she took three weeks to give JFK Jr. a response might seem to some like she didn't really want to move ahead with their engagement.

Carolyn Bessette was hurt that John F. Kennedy Jr. never introduced her to his mother, Jacqueline "Jackie" Kennedy Onassis. Talk about two women who would have a lot in common! While Bessette became a trendsetter for her love of quiet luxury, Jackie was a master of political fashion. She made everyone believe that the boucle jacket was the sophisticated trend that every wardrobe needed, and she wasn't wrong.

Bessette took it as a sign that JFK Jr. wasn't serious about her. In the early '90s, he was figuring out his relationship with Daryl Hannah, giving Bessette the runaround until he and Hannah broke up in 1994. While he had been casually seeing Bessette as well, he never introduced her to his mother. Tragically, Jackie died on May 19, 1994, before he got the chance to arrange a meeting between the two. John was also bogged down with his political magazine, "George," a publication that would eventually fail. "I think it was hard for him to take anything other than his work too seriously at that moment," author Elizabeth Beller wrote in her book, "Once Upon A Time: The Captivating Life of Carolyn Bessette-Kennedy." "If Carolyn met Jackie, I think he knew that that would sort of become a life of its own. And maybe he wasn't quite ready for that."

John F. Kennedy Jr. grew up with media attention all around him. Rather than avoiding it, he sought it out. Paparazzi attention was something that Kennedy gravitated towards, and he would even exercise shirtless in Central Park to make sure that the cameras got something riveting. "If he wasn't in the papers for a short period of time, I guarantee you, no matter what the weather he'd be outside playing football with his shirt off," author Steven Gillon told The Post, via Page Six. Apparently, Kennedy was a ham for the camera.

For Bessette, it was a completely different story. She found the hoards of paparazzi outside of their Tribeca apartment overwhelming. Bessette attended Gianni Versace's funeral in Miami on July 22, 1997, and sat behind Princess Diana. When Diana died only weeks later, Bessette became even more worried about the invasive photographers, because the princess' death was largely caused by a paparazzi chase. "Carolyn was horrified by Diana's death," RoseMarie Terenzio, Kennedy's assistant at "George," told People. "[Bessette] was also rattled by the fact that it could happen to John — that it could happen to her. She feared, 'Now they're going to focus on us even more because they don't have her.'" Kennedy and Bessette were on completely different pages when it came to media attention, and the differing reactions drove a wedge between them.

Harder yet for the couple was the fact that Carolyn Bessette didn't like spending time with John F. Kennedy Jr.'s family. While lauded by most of the world as American royalty, for Bessette, the Kennedy's were poor company. The Kennedy's close-knit bond, sometimes too close, was irksome to her.

Conversely, JFK Jr. enjoyed spending holidays and weekends at Hyannis Port, Massachusetts, on Cape Cod — the location of the famous Kennedy compound. Bessette found the company of Ethel Kennedy, Robert F. Kennedy's widow, particularly trying. While Ethel could be regal and uncompromising, she did try her best to impart her own hard-earned wisdom to Bessette. When Bessette admitted to feeling insecure with John, Ethel was surprised because Bessette was so beautiful and intelligent. According to J. Randy Taraborrelli's book "The Kennedy Heirs," Ethel admitted to struggling with that herself. "I went through that with Bobby at first," Ethel said, according to Taraborrelli. "Then I finally got it that the only way to survive in this family is to look in the mirror and say 'You know what? I'm enough.' Eventually it will sink in and no one can ever take that way from you. Not even the Kennedys." But in spite of these olive branches of advice, Bessette never particularly warmed to the Kennedy clan.

One of the most infamous and unfortunately well-documented moments in Carolyn Bessette and John F. Kennedy Jr.'s relationship was a public fight they had in 1996 in Washington Square Park. Steven M. Gillon, a friend of Kennedy, wrote in his 2019 book "America's Reluctant Prince" that "[the] cause of this infamous fight, and the many that followed, stemmed from Carolyn's ongoing complaint that John let people walk all over him."

A nearby photographer captured the whole thing. The two got into a screaming match, and Kennedy tried to take off Bessette's engagement ring. "Carolyn was trying to grab the dog leash, and he physically pushed her back over and over again," photographer Angie Coqueran told the Daily Mail. "It looked like he was going to smack her in the face." When Kennedy walked away, Bessette ran after him and tried to tackle him from behind. When he turned towards her, she shoved him. Such a heated altercation in public set a bad tone for their relationship; clearly, things could get much more volatile between them than the public knew.

John F. Kennedy Jr. and Carolyn Bessette were allegedly navigating the possibility of divorce in the weeks leading up to their deaths. The two were under considerable strain. Kennedy's cousin and close friend, Anthony Radziwill, was dying of cancer; Kennedy was desperately trying to keep his political magazine, "George," afloat; and Bessette was struggling with the pressures of unwanted and relentless paparazzi attention. They were in marriage counseling to try and work things out.

In the last week that Kennedy was alive, he spent a night — maybe several — at the Stanhope Hotel in New York, not at his apartment with Bessette. He even reconnected with an ex-girlfriend that week for lunch. Two days before the crash, Kennedy allegedly called a friend from his hotel and is claimed to have said of his and Bessette's ongoing conflict, "I've had it with her! It's got to stop. Otherwise we're headed for divorce," per Vanity Fair. In fact, their fight was the reason why her sister, Lauren Bessette, was on the fateful flight with them. Lauren offered to come with them to Kennedy's cousin's wedding at Hyannis Port. She thought her presence could soften the tension between the couple. Tragically, John, Carolyn, and Lauren all died in the plane crash on July 16, 1999, leaving the fate of Carolyn and John's marriage a mystery forever.