The Complicated Reality of JFK Jr. and Carolyn Bessette’s Relationship

Tyler Henry Unknowingly Connects to Carolyn Kennedy in Carole Radziwill Reading

Carolyn Bessette didn’t say yes when John F. Kennedy Jr. first proposed to her.

She didn’t say no, either, but remarkably the 29-year-old Calvin Klein publicist, who had been dating the eligible bachelor for about a year (after several years of the run-around), wasn’t yet sure that she was ready for what marrying him would entail. Namely, a merging of lives that would come with a host of perks but also require a daunting amount of self-sacrifice, not even including the matter-of-fact assault on her privacy.

Carolyn had spent enough time at the Kennedy family compound in Hyannis Port to know that there was no exaggerating the legend behind the larger-than-life name, a family technically made up of flesh and blood just like any other but which had embedded itself in the very fabric of American culture over the greater part of the 20th century.

And she wasn’t bowled over by the Kennedy bond. Rather, the clannishness turned her off.

How Did John F. Kennedy Jr. and Carolyn Bessette Meet?

John met Carolyn in 1992 when she was called upon to oversee a VIP Calvin Klein fitting for the former first son. And he was instantly smitten. 

“Early on, he would be frustrated,” attorney Brian Steel, who met John when they both worked in the Manhattan District Attorney’s office, recalled in the 2018 ABC News special The Last Days of JFK Jr. “He would say, ‘I called her and she hasn’t called me back.’ And John did not like that.”

Gustavo told People in 2014 that Carolyn “didn’t think he was serious. He couldn’t believe she turned him down. It had never happened before.”

“She was exactly the kind of girl I imagined would date someone like John Kennedy Jr.,” RoseMarie recalled in her 2012 book Fairy Tale Interrupted, “and she intimidated the hell out of me.” When she first met Carolyn, though, RoseMarie could tell she “was different from the typical gorgeous girls you see around Manhattan. She wasn’t trying too hard. She wasn’t trying at all.”

Carolyn was playing it cool, but she was acutely aware of who John was. “I kept having to say, ‘Snap out of it, he’s just a guy,” she told the future Carole Radziwill (née DiFalco), who was about to marry John’s cousin and best friend Anthony Radziwill in August 1994.

He was at least partly motivated to take that next step by grief: His mother, who he was extremely close to, died in May 1994 and, in the summer of 1995, Anthony was given a dire prognosis when the testicular cancer he successfully battled in the 1980s returned.

So, after a year of being with Carolyn, he was ready to seize the day, in more ways than one. That September, with his fiancée by his side, John announced the launch of his glossy magazine George, a publication he envisioned would uniquely meld the worlds of politics and celebrity that were already inextricably linked. Cindy Crawford, dressed as George Washington and photographed by Herb Ritts, famously graced the cover of the inaugural October/November 1995 issue.

“It felt like a victory not just for John, but for Carolyn,” Richard Bradley, who served as executive editor at George (and went by Richard Blow in those days), was quoted in The Kennedy Heirs. “She was excited about John, about his drive and determination and the fact that he’d found something that gave him purpose. She wanted to be with him the whole way. She told me she had a sense that this was the first of a series of magazines John might publish, and she had an idea about a style magazine for men, something like Esquire but more mainstream.”

“When you were with them,” Richard continued, “you felt John had really put forth a new power couple in the family, and there had been a lot of them, like Jack and Jackie, Bobby and Ethel, Sarge and Eunice [Shriver]. John had always had a thing about the Kennedy power couples of the past, and this was how he wanted to view himself and Carolyn. So, I guess one could say that Carolyn was becoming the woman behind the man, and John was happy and proud about it. I think his mom would have been as well.”

And importantly for Carolyn, who did her best to ignore the women of all ages who shamelessly threw themselves at her fiancé, John wasn’t too old-fashioned. Unlike so many of the men in his family, including his late father, President John F. Kennedy, he aspired to take their relationship, and their eventual marital vows, seriously.

“I see what goes on in this family, and it scares me,” Carolyn had admitted to her friend Stewart Price, according to The Kennedy Heirs. He reminded her that John was different, to which she replied, “It’s a good thing, too. I know myself and I’m definitely not that pathetic Kennedy wife who’ll stay home with the kids while her husband is out screwing around. No. I’m that pissed-off Kennedy wife who’ll be in prison because she took matters into her own hands.”

Poet and Grateful Dead lyricist John Perry Barlow, a close friend and mentor to John since the 1970s, recalled the young man saying that he didn’t want to be “‘that creepy Kennedy who doesn’t care what his girl thinks about anything. I hate those guys.'” 

What Did Carolyn and JFK Jr. Fight About?

So though numerous issues would plague John and Carolyn’s relationship in the months and too-few years to come, by all accounts infidelity wasn’t one of them—though, according to some, Carolyn would tell John during fights that she was seeing an ex-boyfriend.

Her friends didn’t think she would actually cheat, though.

“Carolyn, more than anyone who John had been with, would stand up to him, and confront him, and I think that John to an extent needed that,” historian Steven M. Gillon, a classmate of John’s at Brown University who was later a contributing editor at George, told InStyle in 2019.

That being said, John was still a headstrong Kennedy, possessed of an explosive temper that wasn’t usually mentioned in the rapturous accounts of the political scion’s inimitable charm and infinite potential—though his ex-girlfriends knew better. 

Gillon wrote in his 2019 book America’s Reluctant Prince: The Life of John F. Kennedy Jr., “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.”

In Carolyn’s eyes John was too much of a yes-man when it came to people asking for favors, and according to Gillon she was still mad about a wedding they had recently attended for a couple they barely knew, where it became obvious to her that the groom had finagled New York Times society page coverage by asking her husband to be his best man.

“She may or may not have been right,” Gillon continued, “but she was furious at John for not making a statement by walking out. It was a familiar argument, one she had belabored frequently in private, but this time it leaked into public view.”

Meanwhile, count John’s sister, Caroline Kennedy Schlossberg, among his many family members who thought the fight in the park was a bad sign. No fan of Carolyn’s in the first place, Caroline thought, according to Taraborrelli, that her future sister-in-law should have known to “avoid those triggers while in public.”

Their uncle, Sen. Edward Kennedy, “spoke to John about it to sort of parent him through it, but he told me he didn’t get far because the kid was so shaken and embarrassed,” the late Sen. John Tunney once said about the incident. “This kind of thing reflected poorly not just on John, but on the entire Kennedy family. Also, Ted knew John wanted to be taken seriously as a businessman with George. What had happened had been at odds with the image he was hoping to project in that regard.”

But as many a Kennedy has noted over the years, not a single person has been born into the family—especially not the guys—without eventually feeling the crushing weight of expectations and history upon them.

“People keep telling me I can be a great man,” John, determined to forge his own path, once said. “I’d rather be a good one.” 

Again, however, he was still JFK Jr.

So Ethel decided to have a chat with Carolyn after their little blowup in the park, and she sent a plane to pick up her nephew’s fiancée and bring the young woman to Hickory Hill, the RFK family estate in Virginia.

Did Ethel Kennedy Save JFK Jr. and Carolyn’s Relationship?

Widowed at 40 in 1968 and left to raise 11 children, Ethel sought to infuse her nephew’s insecure partner with some of her own hard-fought stoicism. She certainly understood what it felt like to exist in the shadow of a man’s overwhelming presence.

“I went through that with Bobby at first,” Ethel said, according to the unnamed friend who Carolyn brought with her to Hickory Hill that day for moral support, who shared the story with Taraborrelli. “Then I finally got it that the only way to survive in this family is to look in the mirror in the morning every single day and say, ‘You know what? I am enough.’ Plain and simple. That’s it. ‘I am enough.’ Eventually it sinks in that, yes, you are enough, and that no one can ever take that away from you. Not even the Kennedys.”

Ethel also said, according to this witness, “Carolyn, I will tell you what I’ve told my daughters and my daughters-in-law. Be there for your husbands, but do not let them influence you into bad behavior. They will bait you. They always do. I’ve seen it for years. But you can’t take the bait. You must be stronger than that.”

Translation: No more screaming at each other in public, period. 

“Never in public,” Ethel pressed. “These men are hotheads. Don’t let them goad you into acting improperly in front of the whole world.” She also is said to have told Carolyn, “I think you’re more powerful than any of the other women John has dated. You know why? Because you’re smart, and because you have heart. So don’t let John or those reporters or photographers or anyone else change who you are in here.” She tapped Carolyn’s chest. “Do you understand?”

The Kennedys booked up all the rooms at the Greyfield Inn, the only hotel on the island, and rented a few private homes. Carolyn printed the wedding programs at the George office after hours, and RoseMarie helped with all the planning, including the setting up of a fake itinerary that would put John and Carolyn in Ireland that weekend. John personally called everyone a week beforehand to invite them to a party.

At one point a helicopter came into view as guests were leaving for the church, but after briefly circling overhead, it went away.

Carolyn wore an instantly iconic Narciso Rodriguez crepe silk slip dress and Manolo Blahnik heels. John wore a dark blue suit and his father’s watch. Caroline was Carolyn’s matron of honor (at John’s request), while her daughters Rose and Tatiana were flower girls and son Jack was the ringbearer. Anthony Radziwill was John’s best man. Sen. Ted Kennedy and John Perry Barlow were also among the 50 people who made the cut.

They enlisted trusted Kennedy wedding photographer Denis Reggie to chronicle their big day, and he’s the one who shot that one photo released to the press, of John kissing his bride’s hand as they left the church.

“The elegance and less being more and not making it a grand occasion but a warm and loving, memorable weekend—I thought that they pulled it off magnificently,” Reggie remembered to TODAY in 2021. Of the image he captured, “I thought there was a magic there. You can see in her face, in Carolyn’s face, surprise and elation and love and romance and all those wonderful things.”

And so John F. Kennedy Jr. and Carolyn Bessette-Kennedy embarked on their next chapter together as husband and wife. 

But making it official didn’t change their clashing temperaments, their communication issues and certainly not the press’s consistently rabid interest in their lives, the paparazzi obviously hoping for a follow-up to their February 1996 performance in the park.

In July 1997, Carolyn went to Milan to attend the funeral for Gianni Versace, who had been murdered outside his Miami Beach mansion. Sitting right in front of her was Princess Diana, who John once had tea with at the Four Seasons in New York. The Princess of Wales had said no to being on the cover of George, but John was utterly charmed.

Five weeks after Carolyn briefly met Diana, the princess was killed in a car crash in Paris along with her boyfriend, Dodi Fayed. Their driver had been speeding through a tunnel trying to lose the paparazzi on their tail when he slammed into a pillar.

“I’m not sure what I’m going to do about Carolyn,” John told his friend Billy Noonan. “She’s really spooked now.”

Was JFK Jr. and Carolyn Bessette-Kennedy’s Marriage in Trouble?

RoseMarie was worried what Carolyn’s absence from the wedding would look like to the outside world, yet another sign of trouble in paradise. She told John that he had to bring Carolyn with him. In her book, she wrote that she told her boss’ wife straight up, “Carolyn, are you f–king kidding me? What are you doing? You’re smarter than this. You don’t want to put John in a position where he has to explain where you are, and you don’t want to put yourself in a position of being judged. You get enough of that.”

RoseMarie and Carolyn’s sister Lauren Bessette, who had lunch with the couple on July 14, 1999, agreed with her brother-in-law that Carolyn would have fun.

John promised he’d never make her go to another big Kennedy compound to-do after this one. Lauren, 34, an investment banker at Morgan Stanley, was going to fly with them, too; they’d drop her off at the airport on Martha’s Vineyard and hop on over to Hyannis Port.

And yet also on July 14, Richard Bradley remembered to Vanity Fair that he overheard John screaming at Carolyn on the phone through his office door. 

“In startling, staccato bursts of rage, John was yelling,” Bradley said. “His yells would be followed by silences, then John’s fury would resume. At first I could not make out the words. Then after a particularly long pause, I heard John shout, ‘Well, goddamnit, Carolyn. You’re the reason I was up at three o’clock last night!’ The shouting lasted maybe five minutes, but John’s office door stayed shut for some time.”

“She told me she felt manipulated and compromised, as if she had no authority over her own life,” Carolyn’s friend told Taraborrelli. “She said she was putting John on probation. ‘I’m going to give it three more months and see how I feel,’ she said.” Carolyn admitted she might be over-dramatizing the situation, but she said she needed “a cooling-off period and that in a few months she’d have more clarity. They’d been having a lot of marital problems lately, she said, and she was worn down by then.”

But, the friend was admittedly wondering at the time, “Who divorces John Kennedy Jr.? You’d have to be insane, or at least that’s what people will think.”

The couple had started marriage counseling that March. “It’s all falling apart,” John lamented to another friend from his perch at the Stanhope.

And he didn’t just mean his marriage. George was in serious financial trouble, the publishing business being notoriously difficult even then, before the death knell of print had sounded, and John went to meet potential investors in Toronto in early July. He flew himself up there, with a copilot.

But even if he lost his magazine, he was determined not to lose Carolyn, and he was looking forward to putting that plan into action somehow during Rory’s wedding weekend.

“Had he not crashed the plane, it would have been a meaningless few weeks of tension,” a close friend of John’s told People in 2017 about John and Carolyn’s much-dissected and now legendary marital troubles, “but it took on a life of its own because it was the last chapter of their life. One week they could have been at war, and the next week they could be right back in love—we’ll never know.”

Ted Kennedy delivered the eulogy for his nephew at a memorial service held on July 23 at the Church of St. Thomas More on New York City’s Upper East Side.

He was a devoted son and brother, “and for a thousand days, he was a husband who adored the wife who became his perfect soul mate,” the senator, who died in 2009, said. “John’s father taught us all to reach for the moon and the stars. John did that in all he did—and he found his shining star when he married Carolyn Bessette.”