A Timeline of JFK Jr.’s Relationships and Carolyn Bessette-Kennedy

John F. Kennedy Jr. and the wife Carolyn Bessette-Kennedy they had a high level of love until their tragic deaths.
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 down with Bessette-Kennedy. As he was expected to follow in his father’s footsteps, President John F. Kennedymany thought Besette-Kennedy would be next Jackie Kennedy.
Many members of Kennedy’s inner circle knew Bessette-Kennedy was “The One” for Kennedy Jr. right away. The Real Housewives of New York City alum Carole Radziwillwho was once married to Kennedy Jr.’s late cousin, Anthony, recalled in a 2016 A&E special that Kennedy Jr. and Bessette-Kennedy had a special connection.
“I met some of John’s ex-girlfriends, but I knew the minute we told Carolyn it was her,” said Radziwill. “He was really excited for her … There was this instant chemistry.”
Kennedy Jr. and Bessette-Kennedy tied the knot in 1996. Rumors that they were having a rough time plagued the two, and they were photographed arguing in public from time to time.
Tragedy struck in 1999. Kennedy Jr. and Bessette-Kennedy died in a plane crash near Martha’s Vineyard. Years after their deaths, reports surfaced that Kennedy Jr. and Bessette-Kennedy were working through their medical problems and hoping to start a family.
“Towards the end of their lives, they were able to reach this kind of harmony,” The Day John Died the writer Christopher Andersen you are only told Us Weekly July 2024. “Any conflict that existed was dealt with.”
The romance of Kennedy Jr. and Bessette-Kennedy was revisited in the 2026 FX limited series Love Story. Keep scrolling to live the timeline of their relationship:

1992
Kennedy Jr. met Bessette-Kennedy while working in sales at a Calvin Klein store in Manhattan.
1994
The couple didn’t officially start dating until two years after their first meeting.

1995
Kennedy Jr. proposed to Bessette-Kennedy on the Fourth of July after one year of dating.
1996
The couple walked down the aisle in an engagement ceremony at a small church on Cumberland Island in Georgia.

1998
Bessette-Kennedy and Kennedy Jr. visited their friends Betsy Reisinger again Kenan Siegel‘s Miami wedding in March 1998. In the book 2024 Once Upon a Time: The Fascinating Life of Carolyn Bessette-Kennedy by ELizabeth BelleReisinger recalled that the two looked like they were in love at his weddings.
“Carolyn and John loved each other deeply and loved life,” he reflected. “That’s how I remember it.”
1999
Kennedy Jr. and Bessette-Kennedy lost their lives tragically on July 16, 1999. Kennedy Jr. was piloting a plane that crashed off the coast of Martha’s Vineyard. Kennedy was 38 years old and his wife was 33 years old. In the accident, Bessette-Kennedy’s sister Lauren also died.



