JFK Jr. and Carolyn Bessette-Kennedy’s Relationship Timeline

John F. Kennedy Jr. and wife Carolyn Bessette-Kennedy had a high-profile romance right up until their tragic deaths.

When the couple began dating in 1994, the world was fascinated by their relationship. Considered to be 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 the footsteps of his father, President John F. Kennedy, many thought Besette-Kennedy would become the next Jackie Kennedy.

Many members of the Kennedys’ inner circle knew Bessette-Kennedy was “The One” for Kennedy Jr. right away. The Real Housewives of New York City alum Carole Radziwill, who 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 met some of John’s previous girlfriends, but I knew the minute he introduced us to Carolyn that she was it,” Radziwill said. “He was really besotted with her … There was this instant chemistry.”

Kennedy Jr. and Bessette-Kennedy tied the knot in 1996. Rumors that they were having their ups and downs dogged the twosome, and they were photographed arguing in public on occasion.

Tragedy struck in 1999. Kennedy Jr. and Bessette-Kennedy were killed in a plane crash near Martha’s Vineyard. Years after their death, reports surfaced that Kennedy Jr. and Bessette-Kennedy were working on their issues in therapy and hopeful to start a family of their own.

“Toward the end of their lives, they had managed to reach this kind of rapprochement,” The Day John Died author Christopher Andersen exclusively told Us Weekly in July 2024. “Whatever friction was there was being dealt with.”

Kennedy Jr. and Bessette-Kennedy’s romance was revisited in FX’s 2026 limited series Love Story. Keep scrolling to relive their relationship timeline:

1992

Kennedy Jr. met Bessette-Kennedy while she was working in sales at the Calvin Klein store in Manhattan.

1994

The couple didn’t start dating officially until two years after their initial 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 intimate ceremony at a small church on Cumberland Island in Georgia.

1998

Bessette-Kennedy and Kennedy Jr. attended their pals Betsy Reisinger and Kenan Siegel‘s Miami wedding in March 1998. In the 2024 book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy by Elizabeth Belle, Reisinger recalled the duo looking infatuated with one another at her nuptials.

“Carolyn and John were deeply in love and in love with life,” she reflected. “That is 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 while his wife was 33. In the crash, Bessette-Kennedy’s sister Lauren also perished.