In the eyes of many, John F. Kennedy Jr and Carolyn Bessette lived the perfect marriage, and their love story was like a fairytale.

But behind the facade, the golden couple of the ’90s struggled.

Almost everyone can probably recall how tragically their story ended – I can still remember the shock when I heard about that fatal plane crash on July 16, 1999.

But not that many know what was reportedly going on in JFK Jr’s bedroom – just 48 hours before he and Carolyn boarded the plane that sealed their fate…

Nobody really knows exactly when JFK Jr. and Carolyn Bessette first laid eyes on each other, but what we do know is that the couple felt an instant connection. There are various reports of the pair’s first meeting. Some suggest that their paths crossed while jogging in Central Park in 1990 – others claim they met at a society event in 1994.

In any case, most indicate that their fairytale romance began when Carolyn was working as a publicist for Calvin Klein and John Jr. came in for a fitting in 1992. At that time, John Jr. was dating actress Daryl Hannah.

According to a friend of the couple, John F. Kennedy Jr fell head-over-heels when he saw Carolyn with her luminous blonde hair and thin brows.

But the son of the 35th President of the United States was met with some resistance at first.

”She didn’t think he was serious. He couldn’t believe she turned him down. It had never happened before,” Gustavo Paredes, a friend of the couple, told People in 2014.

”[He] kept figuring out a way to keep coming back to the showroom for more business meetings and more fittings.”

In 1994, the couple started dating in secret. Carolyn soon moved in with JFK. Jr in his apartment located in the up-and-coming area of Tribeca, which helped the Manhattan neighborhood gain a better reputation.

JFK Jr Carolyn Bessette

Carolyn Bessette, born in 1966 in White Plains, New York, was not like any other woman JFK Jr. had met before. Her mother and dad divorced while Carolyn was young, and she grew up with her mom and stepfather in Old Greenwich, Connecticut.

John Jr. had previously dated high-profile celebrities such as model Cindy Crawford and actress Sarah Jessica Parker – Bessette lacked the type of glamour that surrounded JFK. Jr and his previous love interests.

However, Carolyn had been busy climbing the career ladder and had made a name for herself in the fashion industry. She was working a lot with high-profile clients at Calvin Klein, so she was used to being surrounded by celebrities. Of course, dating the son of former US President John F. Kennedy and Jackie Kennedy was on a whole different level – something that Carolyn would become painfully aware of as their romance evolved.

John F. Kennedy Jr. was born in 1960, 17 days after his father got elected president. From the moment he arrived in the world, John F. Kennedy Jr. caught the interest of the public; he basically grew up in the spotlight.

In fact, his whole life was documented in newspapers, documentaries, and by the paparazzi. As he grew up into a young and handsome bachelor, the tabloids couldn’t stop digging into his love life.

That’s why John Jr. tried to be discreet and tight-lipped regarding his private life. For example, he consistently denied reports of being engaged to Carolyn Bessette. But now we know that he actually popped the question in 1995 when they celebrated the Fourth of July at Martha’s Vineyard. According to some sources, Carolyn waited three weeks before she accepted the proposal.

“She held off the proposal for about three weeks. I think it made him all the more intent on marrying her,” JFK Jr’s former assistant Rose Marie Terenzino told People.

JFK Jr wife wedding dress

When John Jr. snuck away and married his heartthrob in 1996, the pair managed to keep the wedding a secret from the tabloids and the paparazzi. The ceremony was held in the First African Baptist Church on Cumberland Island, built by enslaved African Americans in 1893.

Only one photo emerged from the wedding, a precious picture where John could be seen kissing a smiling Carolyn’s hand. During the private ceremony, the bride wore a pearl-white silk crêpe with a cowl décolletage. The dress was designed by Carolyn’s close friend, Narciso Rodriguez.

View from outside of tiny First African Baptist Church where John F. Kennedy Jr. & publicist Carolyn Bessette held their secret wedding on Cumberland Island off coast of GA.
(Getty Images)

The couple exchanged their vows in front of 40 people, and some of John’s famous relatives were on the guestlist, including Senator Ted Kennedy.

”You could tell right away that there was something special between the two of them,” the senator later told the press.

Unfortunately, John’s mom couldn’t be there. Former First Lady Jackie died two years before the wedding, but it’s clear that John thought about both his parents during the ceremony. For example, he honored his late father by wearing one of JFK’s watches.

After the marriage, Carolyn became one of America’s most famous women, and a swarm of photographers followed her and her husband everywhere.

The ”wolfpack” of photographers chased her down the road, waited outside her doorstep, and cornered her when she was taking the elevator. John. Jr was used to all the attention and the press, but Carolyn was much more of a private citizen. As a result, she came to hate the paparazzi.

“She couldn’t take it. She wasn’t brought up with it. John was, Carolyn wasn’t. She said, ‘I’m terrified of them,’” Jackie Kennedy’s personal assistant, Kathy McKeon, told People in 2017.

Carolyn, who took the name Carolyn Bessette-Kennedy, refused to do any interviews and turned down every offer to appear in different magazines.

What’s more, the media attention harmed her in a way few outside Carolyn’s world could understand. The gossip magazines fabricated all sorts of things about her, calling her “ice queen” and a “miserable wife.” Being constantly compared with her mother-in-law, former First Lady Jackie Kennedy, was another issue.

“If someone was going to steal our prince, the press and the public wanted her to be some kind of unblemished princess,” John’s friend, John Perry Barlow, told People in 2017.

”But Carolyn was not one to be easily defined. She was quirky and imaginative. She was her own self. The woman everyone has read about it not at all as she was in real life.”

During the ’90s, John Kennedy Jr and Carolyn were the golden couple, largely regarded as American royalty. But John wanted the love of his life to “know him as other than the son of the president” and later said that Carolyn had changed his life in a way ”I never thought was possible.”

As mentioned, John loved the fact that Carolyn could stand up to him, and that she was his equal, not his shadow. As a young bachelor, John F Kennedy Jr. enjoyed dating different girls – a trait that might have been inherited by all accounts.

Both his father and grandfather were well-known womanizers, and many men of the Kennedy clan were notorious for their extramarital affairs. Joe Kennedy Sr. was widely known for his infidelity, and John’s father, John F. Kennedy, allegedly had an affair with actress Marilyn Monroe.

But when he married Carolyn, John Jr. did not want to be associated with those kinds of things.

”That creepy Kennedy who doesn’t care what his girl thinks about anything. I hate those guys,” John Jr. told John Perry Barlow, his close friend, and mentor.

But what started as a hopeful love story with much sweetness, later turned into an estranged marriage, according to reports.

In hindsight, people near John and Carolyn have described their relationship as ”passionate and fiery”.

“They would love hard, and they would fight hard,” Ariel Paredes, the granddaughter of Providencia Paredes, who had been an assistant to John’s mom Jacqueline Kennedy Onassis, said.

Rift in the marriage?

During the second half of the 90s, more and more information seeped out about John’s and Carolyn’s marriage troubles. The tabloids were filled with rumors of conflict, abuse, and a potential divorce.

This turbulent time was perhaps most clearly illustrated by a famous quarrel between the couple, which took place right in front of photographers’ eyes in Washington Square in New York.

The paparazzi who stalked the couple suddenly saw how John and Carolyn had engaged in a violent verbal fight. Of course, they didn’t hesitate to take thousands of pictures as the couple shouted at each other. John even tried to tear off a ring from Carolyn’s hand, and the shocking photographs soon wallpapered every newsstand in the United States.

“It looked like Carolyn had brought out the worst in America’s prince, that she was changing him, and a lot of people held that against her,” Richard Bradley, author of American Son: A Portrait of John F. Kennedy, Jr., told E! News.

Several other things also tormented the couple’s marriage and led to skirmishes, according to the press. When JFK. Jr. founded the magazine George in 1995, he put a lot of money into the project, and it attracted great interest. But soon the magazine ran out of money and John found himself under intense pressure. At the time of his death, JFK. Jr was looking for a buyer.

John Jr family and children

It has also been speculated that Carolyn felt overlooked because her husband worked so hard with George.

Another problem of a more private nature was the couple’s views on children. According to Vanity Fair, Carolyn refused to have a family with John, which tormented him. Nevertheless, John dreamed of having a son. He had already decided on a name if he would have a boy: Flynn.

But Carolyn said no.

“I hate living in a fishbowl,” she confided to a friend, according to Vanity Fair.

“John may be comfortable living like this, but I’m not. How could I bring a child into this kind of world?”

During the last months of their lives, it seems like both Carolyn and John were under pressure. Two days before the plane crash that killed them, John F. Kennedy Jr. supposedly opened his heart to a friend and complained about his marriage and relationship with Carolyn.

The author of the article in Vanity Fair, Edward Klein, claims that he talked to a friend of John’s and had the conversation recounted to him. From his fancy hotel bedroom, John talked with his friend over the phone, and said:

”I want to have kids, but whenever I raise the subject with Carolyn, she turns away and refuses to have sex with me. I had it with her!

“It’s got to stop. Otherwise we’re headed for divorce.”

But there are also other statements that contradict the rumors of an impending divorce. Close friends of the couple have subsequently dismissed the claims. Robert Littell spent a weekend together with John and Carolyn just before their deaths – he said he saw no signs of a coming divorce.

Another close friend of the pair, Carole Radziwill, told Vanity Fair:

“[Stress is] hard on any marriage—let alone a young marriage”, adding she had not seen a single ”conversation or anything to indicate there was this impending divorce.”

However, John and Carolyn did see a marriage counselor in March 1999 and sought counseling from Cardinal John O’Connor in the summer of 1999, according to Edward Klein, author of The Kennedy Curse: Why Tragedy Has Haunted America’s First Family for 150 Years.

“Both wanted to improve their marriage. John didn’t want to be one of those Kennedy men who didn’t care how his wife feels,” said The Kennedy Heirs author J. Randy Taraborrelli, according to People.

John F. Kennedy Junior and wife Carolyn Bessette and dog take a stroll in Tribeca. John takes photos with a Leica camera of the photographers. (Getty Images)

JFK Jr plane accident

On July 16, a Friday, John went to work as usual. He had lunch with some of the editors at the George magazine and had a meeting with the staff in the afternoon. He was in an excellent mood, according to his colleagues.

After work, John met up with Carolyn’s sister, Lauren. Together they drove to Essex County Airport in New Jersey. Carolyn met them at the airport, and the trio boarded John’s small plane, a Piper Saratoga he owned. The idea was to get quickly to Hyannis Port, Massachusetts, where they would attend the wedding of John’s cousin, Rory Kennedy.

One of John’s flight instructors would have flown the short distance to Cape Cod with him, but he canceled.

John, who had taken his pilot’s license a year before, got behind the kicks, and the plane took off towards the sunset.

The dark conditions placed high demands on the pilot. At first, however, it seemed as though everything was going according to plan. Then, as the small plane approached Hyannis Port, John Jr. informed the tower at Martha’s Vineyard Airport that he had started to descend.

The tower waited, but no airplane could be seen.

They called the rescue service, which launched a search operation. When they found a suitcase of Carolyn’s in the Atlantic Ocean, most people realized that something terrible had happened.

A few days later, the plane was found using sonar, and according to the autopsy, all three had died instantly when the aircraft crashed into the surface of the water. JFK. Jr.’s body was found strapped into the pilot’s seat – Carolyn and Lauren’s bodies were inside the plane wreck.

According to investigators, the crash was due to John becoming disoriented in the challenging conditions. The sea was pitch black when the plane was about to land, and John lost the ability to determine altitude and speed.

John F Kennedy Jr. was 38 years old at the time of his death; Carolyn was 33.

John Jr Kennedy’s funeral

After their tragic, shocking deaths, the Kennedy family discussed how to honor JFK. Jr. and his wife.

Eventually, the family decided to cremate the bodies and not have a traditional funeral. Instead, John, Carolyn, and Lauren’s ashes were placed in Tiffany-blue boxes and scattered off the coast of their beloved Martha’s Vineyard on July 22.

”John and Carolyn were true soul mates,” the families said in a statement and added that they found ”solace in the thought that together they will comfort Lauren for eternity.”

So sad how their lives ended: May they rest in peace!