John F. Kennedy Jr. and Carolyn Bessette's Relationship: Looking Back at Their Romance and Final Days

JFK Jr. and wife Carolyn Bessette were “working on their relationship” when they died

John F. Kennedy Jr. and Carolyn Bessette-Kennedy’s relationship has been the subject of much speculation over the years, but their passion for each other was undeniable.

The pair, who met in 1992 and wed in a top-secret ceremony on Cumberland Island, Ga., four years later, had their share of ups and downs, with the pair attending marriage counseling before the tragic plane crash that cut their lives short on July 16, 1999.

As John's close friend Sasha Chermayeff shares in a new book, JFK Jr: An Intimate Oral Biography, “He was obsessed from the minute he met her.”

Ariel Paredes, the granddaughter of Jacqueline Kennedy Onassis’s assistant Providencia Paredes, told PEOPLE in 2017,  “They would love hard, and they would fight hard. [But] they were very much in love.”

Keep reading to find out more about the couple’s relationship, from their dressing room meet-cute to their untimely deaths.

They met in a dressing room

Author Elizabeth Beller wrote in her 2024 book, Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, that the magazine editor and the PR rep first met in 1992 in the VIP fitting room at Calvin Klein, where she was working with VIP clientele.

“Calvin — along with his wife, Kelly Klein, and ... assistant MJ Bettenhausen — decided it should be [Carolyn], the most effervescent person on the sales floor, who would show John the selection of clothing,” Beller wrote.

Not only did Carolyn make a sale, sending JFK Jr. home with several new suits, but she also gave him her phone number, which he reportedly called days later.

"[Carolyn] intrigued him more than anyone he’d ever met. A force of nature. He said he wanted to marry her. He was adamant," JFK Jr.'s best friend Robbie Littell said in JFK Jr: An Intimate Oral Biography.

Their first date was a bust

The couple’s first meetup was far from smooth sailing. Bettenhausen told Beller for her 2024 book that Carolyn wasn’t impressed with the company JFK Jr. was keeping at the gala dinner he had invited her to.

“Sitting next to him was another woman that Carolyn either mistook as his date, or actually was his date,” Bettenhausen said. Though the magazine publisher invited Carolyn along to an after-party for the gala, she declined, reportedly telling JFK Jr. she was “meeting people.”

Things turned around for the pair at a May 18, 1992 fundraiser, at which they were seen in “deep conversation” for more than an hour — just the two of them.

Carolyn never met JFK Jr.’s mother

Sadly, JFK Jr.’s would-be wife never got to meet his mother before the former first lady’s death on May 19, 1994 — a fact that became a point of contention between the two. “The on, off-ness of their relationship between '92 and '94, partially, was ... because [Carolyn] would break up with him over the fact that he wasn't introducing her to Jackie,” Beller told PEOPLE in May 2024. “[She was] thinking, ‘This can't be serious if he's not really introducing me to his mother.’ ”

According to Beller, Carolyn was “increasingly irked” that JFK Jr. had met her mother, Ann Messina Freeman, but she had not met Kennedy Onassis. “If Carolyn met Jackie, I think [JFK Jr.] knew that that would sort of become a life of its own,” the author told PEOPLE, adding, “Maybe he wasn't quite ready for that.”

Kennedy Onassis reportedly disapproved of her son’s girlfriend, Daryl Hannah, to whom he was linked to when he met Carolyn. As The Kennedy Heirs author J. Randy Taraborrelli wrote in his 2019 book, "John had measured most of the women in his life by Jackie's opinion of them. If his mother approved, John would decide he wasn't sure. However, if his mother disapproved, as she did with ... Hannah, John became even more attached."

Beller told PEOPLE that JFK Jr. later regretted not introducing his mother to Carolyn, calling it “one of his main regrets.”

JFK Jr. proposed in July 1995 — but Carolyn didn’t accept right away

Despite the fact that JFK Jr. was considered one of New York’s most eligible bachelors, earning the title of PEOPLE’s Sexiest Man Alive in 1988, Carolyn took her time to respond to his July 1995 proposal.

Per Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, John popped the question during a fishing trip to Martha’s Vineyard, telling her, “Fishing is so much better with a partner,” as he slid a platinum ring of diamonds and sapphires on her finger.

According to Beller, Carolyn responded by saying, “I’ll think about it.”

As a close friend of JFK Jr. told PEOPLE in 2017, “She held the proposal off for about three weeks, which I think just made him all the more intent on marrying her.”

Their wedding was an extremely private affair

JFK Jr. and Carolyn tied the knot on Sept. 21, 1996, in a super intimate ceremony on Georgia’s Cumberland Island.

The church they exchanged their vows in held no more than eight pews for their 40 guests, including JFK Jr.'s sister Caroline Kennedy and her husband Edwin Schlossberg and Carolyn's mother and sister Lisa.

Caroline’s daughters, Rose and Tatiana, served as flower girls, while her son Jack was the couple’s ring bearer.

The bride, who was a bit late to the ceremony, walked down the aisle in a simple and stunning $40,000 spaghetti strap slip dress designed by hr friend Narciso Rodriguez.

They celebrated at the Greyfield Inn, where guests indulged in a three-tier cake covered with vanilla butter-cream frosting and flower decorations.

Gogo Ferguson, who hosted the wedding at the Greyfield Inn, gave her first interview about the fairytale wedding weekend in the new book, JFK Jr: An Intimate Oral Biography. Ferguson said, “She looked like a calla lily. ... There was no electricity in the church. I mean that one photo of them of them standing at the altar — so beautiful.”

The newlyweds shared their first dance to Prince’s “Forever in My Life.”

Carolyn didn’t feel like she “fit in” with the Kennedys

Though Carolyn never got the chance to meet her husband’s mother, she did visit his family at the Kennedy Compound in Hyannis Port, Mass.

The trip reportedly shook Carolyn's confidence after she was quizzed on current events over dinner. “Carolyn tried to fit in — and that speaks to her tenacity and her desire to please John,” wrote The Kennedy Heirs author Taraborelli.

Though Carolyn reportedly told friends she had no desire to return to the compound, Taraborelli wrote that she was “summoned” to the home of JFK Jr.'s aunt, Ethel Kennedy, in Hickory Hill, Va., after the couple were seen fighting in Central Park.

According to Taraborelli’s 2019 book, Ethel told Carolyn not to let her nephew goad her into “bad behavior,” saying, “You have to be better than that and you have to be bigger than that."

Taraborelli wrote, "It was tough love because she wanted Carolyn to make it and she sensed her vulnerability."

They were in marriage counseling in their final months.

While JFK Jr. and Carolyn's relationship appeared harmonious from the outside, the couple had begun marriage counseling in the spring of 1999.

Wrote Beller: “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.”

According to JFK Jr.’s close friend Chermayeff, who was interviewed for JFK Jr.: An Intimate Oral Biography, the couple were going through a rough patch amid the impending death of JFK Jr.’s cousin, Anthony Radziwill, to cancer, as well as relentless media attention from the paparazzi.

Anthony’s wife, Real Housewives of New York alum Carole Radzwill, told ABC in a 2017 interview that the couple weren't as far gone as they may have seemed. “To say their marriage was on the rocks is just inaccurate,” she said.

The Kennedy Heirs author Taraborelli added, “They were working on their relationship at the time they died. They thought they had all the time in the world to figure this out.”

Carolyn’s mother warned JFK Jr. never to take both of her daughters flying

On July 16, 1999, the plane JFK Jr. was flying to Rory Kennedy’s wedding with Carolyn and her older sister Lauren onboard disappeared.

Carolyn's mother, Ann Freeman, was reportedly “panic-stricken” at the news. “She said something like, ‘I told him never to take two of my girls up at the same time.’ Terenzio recalled in JFK Jr.: An Intimate Oral Biography. “She was angry,” John's former assistant added.

They died together in a tragic plane crash on July 16, 1999

Tragically, the plane JFK Jr. was piloting crashed into the Atlantic Ocean after he became disoriented while driving through thick fog over Martha’s Vineyard on July 16, 1999.

He, Carolyn and her sister, Lauren died upon impact sometime after 9:40 p.m., according to their autopsies, which were made upon discovery of their bodies on July 21, 1999.

JFK Jr. was 38, while his two passengers, Carolyn and Lauren, were 33 and 34, respectively.

“John and Carolyn were wonderful people. They fell in love, they had a stunning, dreamlike wedding,” Chermayeff said in 2019. “I don’t know what would have come to pass had they not night died that night 20 summers ago — and no one does.”

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