John F. Kennedy Jr. and Carolyn Bessette Kennedy’s ill-fated love story is now the subject of a buzzy new bio-series, Love Story: John F. Kennedy Jr. and Carolyn Bessette, but their romance—as well as the tragedy that ended their lives—has always fascinated the public.
The tumultuous ups and downs of Bessette and Kennedy’s relationship were covered relentlessly by the tabloids at the time and continued to be parsed in memoirs, biographies, and documentaries even after their deaths. And yet, even with all this information, it’s difficult to get a clear picture of their timeline.
Narratives from the people who knew them best occasionally conflict, making details fuzzy and nearly impossible to confirm. Additionally, before their marriage, Bessette and Kennedy had an off-and-on-again relationship that occasionally overlapped with their other off-and-on-again relationships. So it’s entirely possible that not even they knew for sure when their relationship began.
With that caveat in place, here is a timeline of John F. Kennedy Jr. and Carolyn Bessette Kennedy’s life together.
1992: Most reports agree that Kennedy and Bessette meet at a Calvin Klein showroom where Bessette was working at the time. Kennedy had an appointment for a fitting in the VIP room, and Bessette, as the most charismatic person on the floor, was tasked with assisting him, per Vogue. Even though Kennedy was still dating actor Daryl Hannah at the time, he left with Bessette’s phone number.
A short while later, they met again at a fundraiser reportedly called Don’t Bungle the Jungle II. This is when sparks really began to fly.
May 1992: Kennedy brings Bessette to Sea Song, Long Island, to spend a long weekend with his cousin, Anthony Radziwill. Radziwill’s then-wife, Carole Radziwill (yes, that Carole Radziwill), said in a documentary, “We were sharing a summer house, Anthony and I and John, and he brought [Bessette] for Memorial Day weekend. They had been seeing each other for a few months super on the DL. And that’s when I first met her.”
Per an excerpt from Elizabeth Beller’s book, Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, published in People, the relationship took a bad turn after this weekend. At dinner, Kennedy confronted Bessette with a letter he’d received from a friend which claimed that she was a partier out for fame and fortune. He apparently tossed the letter at her and stormed out of the restaurant.
1992-1994: They remain off and on for two years, as Kennedy was also dating Hannah at this time. In the JFK Jr: The Final Year documentary, Kennedy’s former assistant, RoseMarie Terenzio, said that Kennedy remained hot and cold with Bessette for a little while. At one point, the New York Daily News ran a photo of Kennedy and Hannah at a movie premiere together. According to Terenzio, Bessette’s own mother sent her a clipping with the note: “Carolyn, please get on with your life, love mom.”
1994: After Kennedy’s mother, Jackie Kennedy Onassis, dies, he breaks it off with Hannah for good and gets serious with Bessette.
July 1995: Kennedy proposes to Bessette.
In his book, Four Friends: Promising Lives Cut Short, excerpted in Vanity Fair, William D. Cohan writes that Kennedy popped the question over Fourth of July weekend in Martha’s Vineyard. “At one point John asked Carolyn to go fishing. While they were out on the water, John asked her to marry him. ‘Fishing is so much better with a partner,’ he said to her. He added that many things in life are better with a partner.”
He gave her a platinum engagement ring adorned with diamonds and sapphires. Radziwill claimed in her own memoir that the ring’s design was inspired by a ring worn by the late Jackie.
Reportedly, Bessette waited several weeks before saying yes to the engagement.
February 25, 1996: Kennedy and Bessette are photographed in the midst of an epic fight in Washington Square Park. The images seemed to show Kennedy attempting to physically take the engagement ring off Bessette’s finger.
According to Steven M. Gillon’s America’s Reluctant Prince: The Life of John F. Kennedy Jr., Bessette was angry that her fiancé, in her opinion, was letting people take advantage of him. Recently, the couple had found themselves seated beside a New York Times society editor at the wedding of a loose acquaintance, which Bessette clocked as a ploy by the bride to get her wedding on the cover of the paper. “She was furious at John for not making a statement by walking out,” Gillon wrote.
September 21, 1996: Kennedy and Bessette are married on Cumberland Island, Georgia, in a one-room church. The wedding was infamously kept top secret, even from some of the guests.
“It’s almost like they eloped with 30 of their closest friends. It was very much like that,” Radziwill said, per CNN. “You didn’t get the sense that anything was overly planned. They just let things happen the way they happened. And there was something so beautiful about that.”
1999: Bessette and Kennedy’s marriage may be showing signs of strain. Beller told Katie Couric in a podcast that the press scrutiny went into overdrive after the wedding. “She was terrified. Absolutely terrified,” Beller said.
Additionally, Beller wrote in her book that there were disagreements about starting a family, and they began marriage counseling in the spring of 1999.
July 16, 1999: Kennedy is to fly himself, Bessette, and Bessette’s sister to Cape Cod for his cousin Rory Kennedy’s wedding. The plane crashes, killing everyone on board.
