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The ugly early days of JFK Jr’s romance with Carolyn Bessette and his callous act that drove the pair to the brink

May 25, 2024
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The ugly early days of JFK Jr’s romance with Carolyn Bessette and his callous act that drove the pair to the brink


John F. Kennedy Jr confronted Carolyn Bessette with a nasty poison pen letter branding her a user during the early days of their courtship.

Author Elizabeth Beller’s new book Once Upon A Time: The Captivating Life Of Carolyn Bessette-Kennedy details the ugly scene during a 1992 date in Tribeca. 

‘The letter claimed Carolyn was a user, a partier, that she was out for fame and fortune, that Carolyn ‘dated guys around town.’

‘John casually tossed the piece of paper at her, stood and walked out the door,’ wrote Beller in an excerpt printed by the Wall Street Journal.

The writer of the letter has not been identified, but Beller said it was a trusted confidant of JFK Jr’s whose brutal assessment of his girlfriend was taken seriously. 

John F. Kennedy Jr's relationship with wife Carolyn Bessette had a rocky start, according to a new book

John F. Kennedy Jr’s relationship with wife Carolyn Bessette had a rocky start, according to a new book

JFK Jr. took her to dinner at Tribeca institution El Teddy's (pictured) to confront her about a letter he had received

JFK Jr. took her to dinner at Tribeca institution El Teddy’s (pictured) to confront her about a letter he had received

The couple meet when JFK Jr. had an appointment at Calvin Klein's flagship store in Manhattan where Bessette worked

The couple meet when JFK Jr. had an appointment at Calvin Klein’s flagship store in Manhattan where Bessette worked

‘Carolyn stared in shock at John as he departed and then at the correspondence on the white linen tablecloth.’

‘She had recently told a friend one of the main things she liked about John was that ‘he is intentionally down to earth,’ so this felt out of character. She read the letter, folded it and put it in her purse. Then she got up and left.’

Carolyn and JFK Jr. – the second child of US president John F. Kennedy and first lady Jacqueline Kennedy Onassis – started dating in the early 1990s, and they quickly became one of the most talked about couples on the globe.

They wed in 1996, with Bessette’s simple slip wedding dress causing a sensation and cementing her reputation as an icon of minimalist fashion. 

The couple meet when JFK Jr. had an appointment at Calvin Klein’s flagship store in Manhattan where Bessette worked.

Calvin, his wife Kelly Klein, and Calvin’s assistant MJ Bettenhausen agreed Bessette should join them for JFK Jr.’s fitting. 

‘John invited her to join his group at a gala dinner,’ Bettenhausen told Beller.

When she arrived, JFK Jr. was sitting at the table with another woman. Following the gala he had invited her to an after-party which she decline saying, ‘I can’t. I’m meeting people.’

The biography shows Bessette in a different light as she was previously described as ‘icy’ by headlines. 

Carolyn Bessette is pictured with her sister Lauren in 1998 in New York City. Carolyn, Lauren and Carolyn's husband JFK Jr all died in a plane crash the following July

Carolyn Bessette is pictured with her sister Lauren in 1998 in New York City. Carolyn, Lauren and Carolyn’s husband JFK Jr all died in a plane crash the following July 

Massachusetts State Police are seen searching for wreckage following the July 1999 crash off the coast of Martha's Vineyard

Massachusetts State Police are seen searching for wreckage following the July 1999 crash off the coast of Martha’s Vineyard  

Beller highlights Bessette’s ‘compassion’ as she shares that she urged JFK Jr. to call Prince William and Prince Harry following their mother’s 1997 death, however, the attorney refused to pick up the phone because of Diana’s extremely public passing.

The public already had an immense fascination with the Kennedys, but Bessette’s bold fashion choices and her ability to turn even the simplest looks into a chic ensemble only drew people in even more.

Her shocking and premature death aged just 33 in a July 1999 small plane crash alongside JFK Jr and her sister Lauren has only served to enhance Bessette’s mystique. 

Friends say the couple were having serious marital problems and predict the marriage would likely have ended were it not for the crash that claimed their lives. 

JFK Jr was flying the small Piper Saratoga plane at the time with his inexperience as a pilot blamed for the tragedy.

Members of the Kennedy and Bessette families stand on the Coast Guard boat Hammerhead on their return from a burial at sea for John Jr., his wife Carolyn and her sister Lauren G on 22 July 1999 in Woods Hole

Members of the Kennedy and Bessette families stand on the Coast Guard boat Hammerhead on their return from a burial at sea for John Jr., his wife Carolyn and her sister Lauren G on 22 July 1999 in Woods Hole 

He likely became disorientated while flying at night, with the plane crashing into the Atlantic off the coast of Martha’s Vineyard. 

Other pilots flying in the area that night said the horizon was impossible to see because of hazy weather.

The bodies of JFK Jr, Carolyn and Lauren were found five days later, cremated and buried at sea the following day. 

In October, Bessette was dubbed a ‘ghost influencer’, with top fashion brands once again touting her simple but elegant 1990s looks. 

The New York Times pointed out that many of Bessette’s style staples – like pencil skirts, slip dresses, loafers, and overcoats – have popped up on the runways at New York Fashion Week recently, while branding her as ‘the ghost influencer of the season.’

She famously wore a white, button down top tucked into a figure-hugging, floor-length black skirt during one of the last appearances she made before her death.

And now, multiple brands – including Peter Do, Dior, and Fendi – have showcased similar looks in their latest collections.

In addition, the clothing company Sporty & Rich re-created some of her and JFK Jr.’s most well-known paparazzi shots as part of a campaign last month.

‘She was minimalism with character – she wasn’t sterile or boring,’ Wes Gordon, the creative director of Carolina Herrera, told the outlet of Carolyn’s sense of style.



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