John F. Kennedy Jr. and woman Carolyn Bessette-Kennedy they had a high-profile romance until her tragic death.
When the couple started dating in 1994, the world was fascinated by their relationship. Considered one of the most eligible bachelors at the time, Kennedy Jr. decided to settle with Bessette-Kennedy. As expected he would follow in his father’s footsteps, President John F. Kennedymany thought Besette-Kennedy would become the next Jackie Kennedy.
Many in the Kennedys’ inner circle learned that Bessette-Kennedy was Kennedy Jr.’s “The One.” right away The Real Housewives of New York City alum Carole Radziwillwho was previously married to Kennedy Jr.’s late cousin Anthony, recalled in a 2016 A&E special that Kennedy Jr. and Bessette-Kennedy shared a special connection.
“I knew a few of John’s previous girlfriends, but the moment he introduced us to Carolyn I knew she was the one,” Radziwill said. “I was really smitten with her… There was this instant chemistry.”
Kennedy Jr. and Bessette-Kennedy married in 1996. Rumors of their ups and downs dogged the two, and they were photographed arguing in public at times.
Tragedy struck in 1999. Kennedy Jr. and Bessette-Kennedy died in a plane crash near Martha’s Vineyard. Years after his death, reports emerged that Kennedy Jr. and Bessette-Kennedy were working on their problems in therapy and hoping to start a family of their own.
“Towards the end of their lives, they had managed to come to this kind of rapprochement,” The day Joan died author Christopher Andersen explained exclusively Us Weekly in July 2024. “Whatever friction there was, it was being dealt with.”
The romance of Kennedy Jr. and Bessette-Kennedy were revisited in FX’s 2026 limited series Love Story. Keep scrolling to relive the timeline of their relationship:
1992
Kennedy Jr. met Bessette-Kennedy while working in sales at the Calvin Klein store in Manhattan.
1994
The couple didn’t officially start dating until two years after their initial meeting.
1995
Kennedy Jr. proposed to Bessette-Kennedy on July 4 after a year of dating.
1996
The couple walked down the aisle in an intimate ceremony at a small church on Cumberland Island in Georgia.
1998
Bessette-Kennedy and Kennedy Jr. they attended their friends Betsy Reisinger i Kenan Siegelthe miami wedding in march 1998. In the 2024 book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy by Elizabeth belleReisinger recalled that the duo seemed in love with each other at their nuptials.
“Carolyn and John were deeply in love and in love with life,” he reflected. “That’s how I remember them.”
1999
Kennedy Jr. and Bessette-Kennedy tragically lost their lives on July 16, 1999. Kennedy Jr. was piloting a plane that crashed off the coast of Martha’s Vineyard. Kennedy was 38 years old while his wife was 33. Bessette-Kennedy’s sister Lauren was also killed in the crash.