The relationship between Carolyn Bessette-Kennedy and John F. Kennedy Jr. has been closely watched ever since the press first wrote about them. A representative of American political elite and a stylish Calvin Klein PR specialist from New York found themselves in the tabloids’ spotlight: their high-profile romance experienced ups and downs — elegant appearances at galas, a secret intimate wedding, and public arguments in Central Park. The couple’s story ended in tragedy when the small plane, piloted by John F. Kennedy Jr., crashed into the Atlantic Ocean en route to Martha’s Vineyard. On the occasion of the release of the series “Love Story” — a Ryan Murphy anthology in which Sarah Paulson and Paul Anthony-Kelly embody this couple — we recall their story and the key moments that defined this romance.
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The Beginning: A Chance Encounter at Calvin Klein
1992. John F. Kennedy Jr. and Carolyn Bessette met at the Calvin Klein office, where she worked in public relations and collaborated with VIP clients. According to recollections in Lizeller Beller’s biography “Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy” (2024), Kennedy came for a fitting, asked Bessette for her phone number, and invited her to a gala. They barely spoke that time, but by May, they were seen together at another event, conversing for over an hour.
Spring 1994. Over the next few years, Kennedy and Bessette maintained contact, but he was still in a long-term relationship with Daryl Hannah, which finally ended that year — almost concurrently with the death of his mother, Jackie Onassis.
In May of that year, Kennedy let Hannah’s dog off its leash in Central Park, and the animal was hit by a car. According to the book “JFK Jr.: An Intimate Oral Biography” (2024), he flew to Los Angeles with the dog’s ashes for a farewell, despite his mother’s critical condition. Carole Radziwill recalled it as a difficult and unsettling period for him. Shortly thereafter, the couple separated.
The Start of a Serious Romance
After breaking up with Daryl Hannah, John F. Kennedy Jr. began actively pursuing Carolyn Bessette. She was not quick to reciprocate. According to their friend Gustavo Paredes, Carolyn was unsure of his intentions. He recalled in a 2014 People interview: “She didn’t think he was serious. He couldn’t believe she turned him down. That had never happened to him before.”
Kennedy’s friend Brian Steel recalled in a 2019 ABC News special “The Last Days of JFK Jr.” that John reacted painfully when Carolyn didn’t call back. Carole Radziwill recounted in the A&E film “JFK Jr.: The Final Year” that she met Bessette during a shared Memorial Day weekend; they had been dating privately for several months. However, within weeks, Kennedy broke up with her and got back together with Daryl Hannah.
Rosemary Terenzio recounted that Carolyn found out about this from the newspaper. Her mother even sent her a clipping with the words:
“Carolyn, please move on with your life. Love, Mom.” However, that summer, Kennedy and Daryl Hannah finally broke up, and he began a serious relationship with Carolyn Bessette.
The Middle: Proposal, Argument, and Wedding
July 4, 1995. During the Independence Day weekend, approximately a year after their relationship began, Kennedy proposed to Bessette on a fishing boat on Martha’s Vineyard.
Rosemary Terenzio recalled in a 2022 interview with People that during the proposal, John said that everything becomes better with a partner — both fishing and life — and asked Carolyn to be his partner. She didn’t respond immediately and took three weeks to consider, well aware of the level of public scrutiny after marriage. According to Terenzio, this pause only strengthened his resolve.
February 25, 1996. The couple was photographed during an argument in Central Park — the incident became the subject of an eight-page feature in the New York Daily News. According to Stephen M. Gillon’s recollections, conflicts often arose because Carolyn reproached John for being too trusting.
September 21, 1996. Kennedy and Bessette married at Greyfield Inn on Cumberland Island in the presence of only 32 guests. The wedding was kept secret: guests were allowed onto the island using special coins, and no paparazzi learned of the event.
The End: A Difficult Period and Tragedy
1996. After the wedding, media attention to the couple increased significantly. Carolyn craved privacy and refused interviews, leading some in the press to portray her negatively. Upon returning from their honeymoon, John F. Kennedy Jr. approached the paparazzi outside their Tribeca home, asking them to give his wife space to adjust to her new life.
1998 became a difficult year for the family: Kennedy’s cousin Anthony Radziwill was battling a rare sarcoma. According to friends, this tragedy brought Carolyn and John even closer. At the same time, rumors of infidelity linked to Carolyn’s name appeared in the media.
1999. In the book “The Kennedy Curse” (2004), Edward Klein wrote that the couple was reportedly on the verge of divorce in the summer due to disagreements about children: John wanted a family, while Carolyn hesitated, not wanting to give birth under constant media scrutiny. She explained to a friend: “I hate living under constant surveillance. John might be okay with it, but I’m not. How can you bring a child into this world?”
July 16, 1999. During a flight to the wedding of their cousin Rory Kennedy on Martha’s Vineyard, John F. Kennedy Jr., Carolyn Bessette-Kennedy, and her sister Lauren died in a plane crash in the Atlantic Ocean. Their bodies were found on July 20 by U.S. Navy divers. John F. Kennedy Jr. was in the cockpit. Carolyn Bessette-Kennedy and Lauren were strapped into their seats.
Thus ended the story of their romance — a love, publicity, and tragedy that remains a part of cultural memory to this day.
Based on material from vogue.com