Inside Jfk. Jr’s Fairytale Romance with Wife Carolyn Bessette and Their Well-Guarded Secret

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.

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.