Carolyn Bessette-Kennedy and John F. Kennedy Jr.’s relationship has enthralled the world from the moment it first hit the papers. American political royalty and a stylish Calvin Klein publicist from New York found themselves filling tabloids as their high-society relationship hit its highs and lows, with stylish nights out at galas; a secret, intimate wedding shielded from the press; and public arguments in Central Park. The couple came to a tragic end when a small plane piloted by JFK Jr. crashed into the Atlantic Ocean while flying to Martha’s Vineyard.
With the upcoming release of Love Story—a Ryan Murphy anthology series starring Sarah Pidgeon and Paul Anthony Kelly as the ill-fated couple—we’re looking back at Carolyn Bessette-Kennedy and John F. Kennedy Jr.’s relationship and the key moments that defined their romance.
The Beginning: A Chance Meeting at Calvin Klein
1992: John F. Kennedy Jr. and Carolyn Bessette first met when she was working in publicity with VIP clientele at Calvin Klein. The designer’s ex-wife, Kelly Rector, shared in Elizabeth Beller’s 2024 biography Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy that Kennedy came in one day for a fitting. He asked Bessette for her number and to join him at a gala with a group. Kennedy was seated with another woman at the event, so the two did not spend much time together that evening. However, the pair were seen at another gala later that May, talking for over an hour.
Spring 1994: Over the next few years, the two would stay in touch, but Kennedy was also in a five-year on-and-off relationship with actor Daryl Hannah that began in 1989. They would officially split in 1994, around the time Kennedy’s mother, Jackie Onassis, passed from non-Hodgkin lymphoma. In May of that year, Kennedy had lost control of Hannah’s dog in Central Park and a car hit it. In RoseMarie Terenzio and Liz McNeil’s 2024 book JFK Jr.: An Intimate Oral Biography, it was revealed that Kennedy flew to Los Angeles with the dog’s ashes for a funeral Hannah arranged while his mother was dying. Carole Radziwill, who was married to Kennedy’s cousin, shared, “John felt [Daryl] was punishing him by insisting he fly to LA that weekend. It was just a terrible time and a bad omen.” The couple broke up soon after.
Kennedy then began pursuing Bessette in earnest, yet she wasn’t as eager to commit to him. “She didn’t think he was serious,” their friend Gustavo Paredes shared with People in 2014. “He couldn’t believe she turned him down. It had never happened before.” Kennedy’s friend and colleague Brian Steel said in the 2019 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.”
Radziwill recalls Kennedy bringing Bessette on a weekend trip with them in the 2019 A&E documentary JFK Jr.: The Final Year. “We were sharing a summer house, Anthony [Radziwill, Kennedy’s cousin] and I and John, and he brought her for Memorial Day weekend,” said Radziwill. “They had been seeing each other for a few months, super on the DL. And that’s when I first met her.” She added, “And then he broke up with her a few weeks later because he got back with his ex-girlfriend Daryl Hannah.”
“He just kind of went off the radar,” said RoseMarie Terenzio, Kennedy’s chief of staff at George magazine, at a 2019 screening of that documentary. “And then she opened up the newspaper, and there he was at a movie premiere with Daryl. And her mom, who is hilarious, sent her the article in the mail: ‘Carolyn, please get on with your life, Love, Mom,’ with a sad face.” However, Kennedy and Hannah did finally split that summer, and he began dating Bessette seriously.
The Middle: The Proposal, a Fight, and a Wedding
July 4, 1995: On Fourth of July weekend, about a year after they began dating, Kennedy proposed to Bessette in Martha’s Vineyard on a fishing boat. “He went into this thing about how everything’s better with a partner, not just fishing but life,” Terenzio told People in 2022. “He said, ‘I want you to be my partner.’”
However, it was not an automatic yes. The fashion publicist took three weeks before agreeing to marry Kennedy. “She understood that the formality meant something, especially to John and his lifestyle,” Terenzio said in her 2012 book Fairy Tale Interrupted. “He was pretty old-fashioned, and given his place in the world, he couldn’t be single forever. “Terenzio later observed: “I actually think that made John even more eager to marry her.”
February 25, 1996: Kennedy and Bessette were spotted arguing while on a walk in Central Park. A photographer happened to be in the area and captured the verbal altercation, which led to an eight-page spread in the New York Daily News. The fight reportedly included Kennedy trying to take the engagement ring off Bessette’s finger. “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,” wrote Kennedy’s friend Steven M. Gillon in his 2019 biography America’s Reluctant Prince.
September 21, 1996: Only 32 guests joined the couple for their wedding at the Greyfield Inn on Cumberland Island, a secluded destination off the coast of Georgia. “That night there was a wedding—one of the best-kept secrets of modern time,” Radziwill wrote in the Daily Mail in 2019. “There were wild horses and wildflowers. It was untouched and bucolic.”
Radziwill explained that to maintain secrecy, guests needed to present a special Indian nickel upon arrival at the island or they would be escorted off. “We all pulled off the coup of the century that weekend,” she wrote. “John Kennedy Jr., the most famous man in the world, got married on a pastoral, remote island off the coast of Georgia, and no one knew. Not a paparazzi in sight.”
The End: A Difficult Period and Tragedy
1996: After their wedding, media scrutiny of the couple reached new heights. When Bessette-Kennedy sought more privacy and declined interviews, the press turned on her, painting her in a negative light. Shortly after returning from their honeymoon, Kennedy even made a statement to paparazzi camped outside their Tribeca apartment in defense of his wife. “This is a big change for anyone,” Kennedy said, according to William D. Cohan’s 2019 book Four Friends: Promising Lives Cut. “For a private citizen, even more so. I just ask [for] any privacy or room you could give her as she makes that adjustment. It would be greatly appreciated.”
1998: The family faced a difficult period as Kennedy’s cousin, Anthony Radziwill, battled a rare sarcoma. “That was a very painful year [for him], to watch someone he’d grown up with, who was exactly his age and he’s dying,” Kennedy’s high school friend Sasha Chermayeff told Town Country in 2019. “For John, I think that Anthony’s illness brought everybody closer in a good way, including Carolyn and him.”
Later that year, infidelity rumors arose in the press around Bessette-Kennedy’s affair with her ex-boyfriend model Michael Bergin, as well as a kiss that took place with an old friend.
1999: In Edward Klein’s 2004 book, The Kennedy Curse, it was revealed that the couple were on the rocks during the summer of 1999, largely over discussions about having children. “I want to have kids, but whenever I raise the subject with Carolyn, she turns away and refuses to have sex with me,” Kennedy told a friend in July that year, according to Klein’s book. “It’s not just about sex. It’s impossible to talk to Carolyn about anything. We’ve become like total strangers.” He continued: “I’ve had it with her. It’s got to stop. Otherwise we’re headed for divorce.”
According to the book, Bessette-Kennedy was hesitant due to the media. “I hate living in a fishbowl,” she shared with a friend. “John may be comfortable living like this, but I’m not. How could I bring a child into this kind of world?”
July 16, 1999: When traveling to the wedding of cousin Rory Kennedy in Martha’s Vineyard, the couple and Bessette-Kennedy’s sister Lauren died in a plane crash in the Atlantic Ocean. Their bodies were discovered on July 20 by Navy divers: Kennedy, who had been training to gain experience as a pilot, was found in the cockpit, and the others were strapped into their seats.
