Inside Carolyn Bessette-Kennedy and JFK Jr.’s Tempestuous Love Affair (Exclusive)

Nearly 25 years after her death, there’s still an air of mystery about Carolyn Bessette-Kennedy, the enigmatic woman who married John F. Kennedy Jr. in 1996.

After her death on July 16, 1999, at age 33, when the plane piloted by John, 38, also carrying her sister Lauren, 34, crashed off the coast of Martha’s Vineyard, she remains celebrated as a style icon on countless Instagram accounts.

But as Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy by Elizabeth Beller reveals, there was so much more to who she truly was. “People wrote about her so harshly and cast her as icy,” says Beller, “but she was a lioness, effervescent, warm and so full of life.” 

After graduating from Boston University with a degree in education, she worked in the city’s Calvin Klein boutique and then moved to New York in 1989, where she began working in VIP sales for the minimalist designer. That’s where she first came across JFK Jr. Below, read an exclusive excerpt from Beller’s book about what happened from there.

‘Once Upon a Time’ by Elizabeth Beller.

Gallery Books

In spring 1992, Calvin Klein was just getting back into menswear. None other than John F. Kennedy Jr. had an appointment for a fitting and [Calvin decided] Carolyn should show John the selection. He came out of the meeting smitten, with a few suits and Carolyn’s number.

“John invited her to join his group at a gala dinner,” recalled [Calvin’s assistant.] “Sitting next  to him was another woman that Carolyn either mistook as his date, or actually was his date.” It was unclear, and Carolyn wasn’t pleased. 

But when they met again at a May 18 fundraiser, they were spotted in deep conversation at the bar. 

John and Carolyn stayed there for over an hour, never looking away from each other. Lightning had struck.

After the benefit, John and Carolyn continued to see each other, in a haze of sultry dinners, dancing, and walks in Central Park. John even brought Carolyn to Sea Song, the Long Island, home he rented with his cousin, Anthony Radziwill.

The week after that, Carolyn met John for dinner at El Teddy’s, where he presented Carolyn with a letter [from] a friend of his. The letter claimed Carolyn was a user, a partier, that she was out for fame and fortune [and] “dated guys around town.” John casually tossed the piece of paper at her, stood, and walked out the door. Carolyn stared in shock at John as he departed.

John meanwhile, had been spotted about town with Daryl Hannah that fall—all documented in the press. Granted, Carolyn knew she wasn’t his only option. When she came across a pair of [former girlfriend] Julie Baker’s duck boots in John’s apartment, despite them being a size too small, she made a point of wearing them. 

For more on Carolyn Bessette Kennedy, pick up the latest issue of PEOPLE, on newsstands Friday, or subscribe here.

But Carolyn became increasingly irked that he wouldn’t introduce her to his mother. “I took him to meet my mom,” Carolyn told a friend. 

Jacqueline Kennedy Onassis.

Bettmann Archive/Getty

“John called all the time,” says [a] Carolyn friend, “[We recorded] an outgoing message on her answering machine.” Anyone who called would get Carolyn saying, “Hey, hon, I’ll be back by seven o’clock, can’t wait to see you!” The idea was that John would hear it and assume she’d moved on. John did—and he called even more.

But behind closed doors, Carolyn and John were developing a real kind of intimacy.

The weekend of July 4, 1995, he asked her to go fishing in Martha’s Vineyard—and proposed.  

He turned to Carolyn and said, “Fishing is so much better with a partner.” Then he put a platinum band of diamonds and sapphires on her finger. Carolyn told him, “I’ll think about it.”

This was also the time when Carolyn lost weight, and plucked her eyebrows to small wisps.  And so when Carolyn stepped into the [Municipal Art Society] gala on John’s arm [on Feb  27, 1996], she had metamorphosed to a platinum siren.

Carolyn Bessette-Kennedy.


She planned their Sept 21 wedding on Cumberland Island, off the Georgia coast, and flew to Paris where her friend, Narciso Rodriguez designed her pearl-colored silk crepe dress.

The ceremony was scheduled to begin at 5 p.m. John had misplaced his shirt, and Carolyn  tried to put her dress on in the car. She forgot that she needed to put the dress on before doing her hair and makeup, which meant redoing both. Just before sunset, Carolyn arrived and was walked down the aisle by her stepfather, Dr. Freeman, as a gospel singer sang “Amazing Grace.”

They returned from their honeymoon to a ravenous press, and the pressure only intensified from there. 

Almost a year later, Princess Diana was killed in a car accident as the result of her driver trying to outrun the paparazzi.  Carolyn was terrified. [She] tried to get John to call Princes William and Harry to give his condolences when it came out that Diana had hoped for her sons to emulate John’s modesty in the face of media obsession. He demurred, as he didn’t know them and thought that their situations greatly differed. 

John earned his pilot’s license in 1998. 

“The only person I’ve been able to get up to go with me, who looks forward to it as much as I do, is my wife,” he [told USA Today]. That she loved flying was probably a reach, [recalls] Bruce Weber. “We both spoke of our dread of flying, especially over those islands off the coast of Massachusetts, because the weather can change so quickly.” 

They began marriage counseling in the spring of 1999. 

A week [after July 4], John had told several friends and colleagues that he and Carolyn were splitting up. Yet, others noted they seemed very happy together, even the weekend before.

After initially refusing to attend his cousin Rory’s July 17 wedding, Carolyn agreed. John would  also fly Carolyn’s sister Lauren from New York to Martha’s Vineyard on their way to Hyannis Port.

Tabloids put forth an alleged timeline in which Carolyn lingered for hours getting a pedicure. Yet an eyewitness report has her leaving the pedicurist by 5 p.m. She went to Saks to buy a dress for the wedding and picked out a black Yves Saint Laurent evening dress. After the purchase, the salesgirl wished Carolyn good luck. “Thanks,” Carolyn replied. “I’m going to need it.”

[John, Carolyn and Lauren] were stuck in traffic and didn’t make it to the airport until after 8 p.m. Before they took off, Carolyn called Carole Radziwill, and they talked about Sunday-night dinner. “The plan,” Carole wrote in What Remains, “was grilled steaks and peach pie.”

When they hadn’t arrived by 10 pm, friends began to worry. 

Carole called the Hyannis Port Airport, Caldwell Airport, Martha’s Vineyard, then the Coast Guard. 

Then, Carole called Ann Freeman and her husband Dick. Dr. Freeman answered, and Carole explained that Carolyn and John hadn’t arrived and there was a search underway. Ann immediately called her back.  “Well, everything’s okay, right? Was anyone else on the plane with them?” Carole was silent. Long enough for Ann to scream. 

For the July 24 Memorial Service in Greenwich, CT, Ann asked Carole to eulogize Carolyn.

She was wild and vivid in a cautious and pale world. Always burning a little more brightly than any of us around her. Then I remembered a story written by Henry James. It was the story of a young girl named Isabel [in Portrait of a Lady]. A girl who was as brave as she was beautiful, who was pure of heart and as unafraid to love…I wondered how it was possible for him to have known her.

From Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy by Elizabeth Beller. Copyright © 2024 by Elizabeth Beller. Reprinted by permission of Gallery Books, an Imprint of Simon & Schuster, LLC.

Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy by Elizabeth Beller is on sale May 21 and available for preorder now, wherever books are sold.

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