The surreal story of John F Kennedy Jr. and Carolyn Bessette from a different perspective

Updated on August 01, 2022 14:28 PM by Ava Sara

Not many know about the love equation between JFK Jr. and Carolyn Bessette. However, to start with their love story, we must start from the middle - when John F. Kennedy Jr. first proposed to Carolyn Bessette.

Any other girl would have jumped up and down and agreed, but that was not the case with Carolyn - she didn't say yes. Carolyn Bessette was always dilemmatic with JFK Jr and their future.

The unexpected proposal

Carolyn Bessette did love spending time with JFK Jr, so she didn't say no to the proposal. However, she was not sure about spending a future with JFK Jr. The 29-year-old Calvin Klein publicist had been dating the eligible bachelor for a year.

She went around with her celebrity boyfriend, John F Kennedy Jr, to dinner and lunch dates. Thanks to the paparazzi who never left them alone anywhere. But, she never thought of John proposing to her to be committed to him for life.

In America, JFK Jr. and Carolyn Bessette were a high-profile ‘celebrity couple.’ However, Carolyn Bessette was not yet sure, even after dating for a year, that she was ready to marry him.

Carolyn was unsure what the marriage would entail as the young lady knew very well that denying JFK Jr was more demanding than trekking the mountains. It was a big decision for Carolyn Bessette to say a yes when she was not confident enough to spend the rest of her life with JFK Jr.

Marrying JFK Jr is not just marrying him; it’s about Kennedys and Bessette's coming together. The marriage would come with a host of perks, as Carolyn Bessette would get to be a part of the Kennedy family, which was a big deal for any girl. Keeping the dating history of JFK Jr., every girl’s dream was to marry JFK Jr.

But, he chose Carolyn over everything, which shocked her a lot. The consequences of this long-term commitment were unavoidable, namely, the merging of so many lives.

The sacrifices she had to make

Along with that, Carolyn Bessette will lose her freedom; she would require an unsettling amount of self-sacrifice. When she tied the knot with John F Kennedy Jr., she stepped into the world of celebrities and regularly exposed her day-to-day life to the camera.

Now, being a celebrity, she could not have removed the paparazzi; her every movement would have been under the harsh scrutiny of the world. Of course, that would even include the rugged practicality of assault on her privacy.

Carolyn Bessette was involved in the family of JFK Jr. During her one year dating JFK Jr., she had spent enough time with the Kennedy family. JFK Jr. was serious about her and wanted to keep her acquainted with every portion of his life.

Carolyn Bessette used to visit the compound in Hyannis Port, where she learned that all the exaggerating legends were true. It wasn’t just being a Kennedy; it’s more like being a part of the larger-than-life name; to be part of a family that is technically made up of flesh and blood like any other.

But that’s it; nothing else matches the Kennedy family and the average Americans. They had embedded themselves in the very fabric of American culture, which made them a household name in America.

They were like the royals of the continental US, especially over the more significant part of the 20th century. The dynasty was always followed everywhere, just like England’s Windsor family. The Kennedys were always under the limelight and scrutiny. As a result, being a part of this family might cost Carolyn a big deal.

She has turned it off already

Carolyn Bessette was an independent woman who believed in her rights and privacy. She knew mingling with the Kennedys was one thing, but getting married was, on the whole, another level—the coming consequences made her realize the truth in the first year of their relationship.

As a result, she was not bowled over by the Kennedy bond, nor was she in the fantasy world. Instead, the dynastical rule of the family turned her off.

Carolyn Bessette did love John a lot, and there was no doubt about it. But that would become the main factor for the rest of their lives. She knew the freedom she would lose; it was not like the jail sentence, which has finite terms; it was more like getting into the psychiatric ward with no release date.

Everything comes with a price, and she was not mentally prepared to pay the fee, even though she had affection for the former President’s son.

Carolyn didn't particularly enjoy spending holidays and weekends with his sprawling family on the Cape. Nevertheless, that was enough for JFK Jr; he wanted the love of Carolyn Bessette, and he was confident that she would not turn him down.

Now, that’s a different issue; she couldn’t have turned him down, even if she wanted to. She understood within twelve months that staying with the Kennedys meant she would always have to maintain a specific protocol.

Maintaining the protocols

Moreover, she did realize that their comings and goings were not under their control; but instead formally presided over by the then reigning matriarch Ethel Kennedy. Now, Ethel Kennedy was Robert F. Kennedy's widow and the ruler of the house other than Jacqueline Kennedy.

It was uncomfortable for Carolyn to get into such restrictions and protocols where the Kennedy men looked like they had been lifted out from a Ralph Lauren ad with their touch football games and clambakes. It was too much for her to maintain so many rules and behave in a certain way to keep up with the Kennedys.

Carolyn Bessette was a free-spirited, independent woman who worked as a publicist in Calvin Klein. She was well-acquainted with the fashion world and knew there was a thin line between sophistication and maintaining specific protocols.

Joining the world of Kennedys meant that she had to get into a particular set of family protocols they had been holding for a prolonged time.

Bessette was not precisely culturally afloat; culture was never a factor for her, as she had unconventional ways of looking at life. She was born in White Plains, New York, and brought up in a posh area of Greenwich, Connecticut.

She lived with her mother and orthopedic surgeon stepfather, but she always felt like an outsider who could not blend into the American culture. Carolyn Bessette has made her career her way without the help of any godfather or godmother.

The insecurities she faced

Her sheer talent made her an independent and confident woman who could make her own decisions. However, things changed after she started dating JFK Jr; she realized being around the Kennedys made her lose her identity.

The fabulous 5-foot-10 inches beauty started feeling small and insecure in the surroundings of the paramount Kennedys. She understood that she could not be herself when she stepped into the world of Kennedys.

Her doubts and uncertainties became prominent on the beach of Hyannis Port. Carolyn witnessed her one-year boyfriend John being a tiny part of the colossal Kennedy machine.

She was shocked and terrified to see that the guy at the Hyannis Port was not the dashing man John F Kennedy Jr. about whom the town had been crazy, nor was he the man whose every movement was detected by the paparazzi in New York.

Carolyn Bessette was looking forward to enjoying more time with John F Kennedy Jr. rather than getting married. Moreover, mingling with the family gave her the idea of the life she would be living if she became a Kennedy. It was tough for her to lose everything and take a huge plunge.

"We don't do insecurity very well," John told his childhood friend Gustavo Paredes.

It was disappointing for him

Gustavo Peredes’s mother, Providencia Paredes, was a longtime aide to Jacqueline Kennedy Onassis. However, they saw the young couple closely back in that time. JFK Jr. commented, "That's definitely not on the Kennedy menu." Now, Carolyn Bessette was not able to get past these red flags.

But then again, he was still JFK Jr., and taking an answer no, was not in his dictionary. He was already disappointed that Carolyn Bessette took so much time to agree when he expected her to jump up and down in happiness.

So, she finally accepted the proposal after three weeks with a heavy heart. At that time, John F Kennedy Jr. was People magazine's Sexiest Man Alive 1988. He was desperate to get married, and he first popped the question to Carolyn Bessette over the Fourth of July weekend on Martha's Vineyard.

It was difficult for Carolyn, but she knew there was no escape; she was already exclusive to JFK Jr., and she could not deny that. But, she was able to make up her mind to get committed to the world’s eligible bachelor.

"I think that made John even more eager to marry her," RoseMarie Terenzio, John's executive assistant, started working under him in 1994. She told The Kennedy Heirs author J. Randy Taraborrelli later on.

It was difficult for JFK Jr. to accept the reluctance of any woman in that manner. JFK Jr. had been in this dating game for a long time, and she was one of those women he had never encountered.

Their first encounter

John F Kennedy met Carolyn Bessette in 1994 at a Calvin Klein-hosted event. It was his first meeting, and Carolyn’s personality and confidence instantly smote him. JFK Jr. always had a fascination for strong women, and Carolyn Bessette was one of them. He found her to be different from the rest. "Early on, he would be frustrated," attorney Brian Steel recalled.

Attorney General Brian Steel met John when they both worked in the Manhattan District Attorney's office. They became friends as JFK Jr. used to share his day-to-day life with him as a co-employee. However, Brian Steel recalled in the 2018 ABC News unique The Last Days of JFK Jr. "He would say, 'I called her, and she hasn't called me back.' And John did not like that."

JFK Jr. was not habituated to these types of responses from women; he has dated various kinds of women, from models to celebrities to film stars, but he has never found someone to be so reclusive about him.

Gustavo Paredes told People magazine in 2014 that Carolyn Bessette "didn't think he was serious. He couldn't believe she had turned him down. It had never happened before." He was taken aback by the frustrations he faced at the hands of this young and independent lady.

"She was exactly the kind of girl I imagined would date someone like John Kennedy Jr.," RoseMarie recalled in her 2012 book Fairy Tale Interrupted. She was strong-headed, and her gentle determination was something that thrilled John.

Carolyn Bessette might be dating JFK Jr., but she never thought of getting married or even dreamed of marrying him. She might appear warm for the first few months, but the more John got closer to her, the more he understood that she was cold and distant from the inside.

It was not that Carolyn ever threatened RoseMarie with a machete or yelled and screamed at her. But, there was something about her that RoseMarie found intimidating. However, Rosemarie did recall that "she intimidated the hell out of me."

Nevertheless, she understood the reason behind John F Kennedy Jr.’s fascination with her. He loved challenges, and she was a challenge for him that he wanted to achieve, and he knew it was not an easy ride. But, he never assigned himself to something manageable.

It was unprecedented for her

There was something different about Carolyn when Rosemarie met her. She could tell she "was different from the typical gorgeous girls you see around Manhattan. She wasn't trying too hard. She wasn't trying at all."

Carolyn Bessette was always reluctant about her relationship with John. She never took him seriously as a full-time committed partner. Carolyn Bessette grew up with her mother and step-dad so suddenly that having a conventional family and living with him wasn't easy for her.

She was not looking forward to having a life with John F Kennedy Jr. knowing that their reputation precedes them.

Carolyn Bessette was always playing it cool to cope with the sudden limelight and attention she was receiving along with the conventional lifestyle of the Kennedy house. She was apprehensive about the right balance between the outside world and a different world of the Kennedys.

She wasn’t finding anything enthusing about getting married to John F Kennedy, knowing the army of people other than the Kennedy clan she would invite into her life.

But, Carolyn was always acutely aware of who John F Kennedy Jr. was. She had to be aware, as she had no other option. It was not easy to get out of the clutches of Kennedys if they had set their eyes on you.

Carolyn realized that John was getting serious about her. "I kept having to say, 'Snap out of it, he's just a guy," RoseMarie told the future Carole Radziwill, née DiFalco.

Carole DiFalco was close to RoseMarie, and they discussed Carolyn and JFK Jr.'s relationship. Carolyn was in a high-profile relationship, so it was evident people would talk about her, let alone JFK Jr.’s inner circle talking about her.

Carole DiFalco was about to marry John's cousin and best friend, Anthony Radziwill. The Kennedys fixed their marriage date as August 1994. So, it was apparent that RoseMarie did share lots of info with Carole DiFalco.

"Carolyn was also worried that marriage would change everything," RoseMarie wrote in her book. She was highly apprehensive about marriage to JFK Jr. and was unprepared to get into this high-profile roller coaster ride.

However, Carolyn could not deny John's presence and charisma. She wanted to spend more time with him, but he wanted to settle down. It was difficult for her to express her inner turmoil with the ongoing changes that were going on at that time.

They started living together

However, the relationship between John F Kennedy Jr. and Carolyn Bessette was profound. He wanted to spend more time with her and wanted her to mingle into his life as soon as possible.

She had already moved into John's spacious loft at 20 North Moore St. in TriBeCa. According to Rosemarie, "she understood that the formality meant something, especially to John and his lifestyle. He was old-fashioned, and given his place in the world, he couldn't be single forever."

Carolyn was a free-spirited woman with no ties, and Kennedys were a close-knitted bond, which made it difficult for her to adjust to the given scenario. John has always been conventional, and staying with him was one of Carolyn's biggest challenges.

She knew where the relationship between them was heading. She anticipated the future but knew she loved him and had no choice.

Previously John had undoubtedly never wanted female company. He had his fair share of girls, from romancing Daryl Hannah to dating Sarah Jessica Parker to landing with Madonna.

JFK Jr. had it all; by the mid-'90s, the eligible bachelor was desperate to settle down. He was the crown prince of the fallen kingdom of Camelot who wanted a true partner by his side.

Luckily he found it in Carolyn Bessette, with whom he was able to see a future. Kennedy men have always been known to be stubborn with the presence of a typical rage that borders with sadomasochism.

Everybody knew about the former President’s fair share of women, even being married to Jacqueline Kennedy. The high-profile love affair between former President John F Kennedy and Marilyn Monroe is still a topic of discussion on various social media pages and forum threads.

JFK Jr. was at least partly motivated to take that next step of settling down by the presence of intense grief: firstly, his mother, Jacqueline Kennedy, died in May 1994, with whom he was extremely close.

Since his father's death, JFK Jr. has always been beside his mother, giving her utmost attention among all the women in his life. Her sudden absence made him feel empty, and he wanted to fill that hole with Carolyn Bessette.

It was the right time for him to find another woman who could fill in the pain he was facing during his beloved mother's sudden demise.

He wanted her in every way possible

In the summer of 1995, Anthony Radziwill was given a dire prognosis of testicular cancer, which he successfully battled in the 1980s and returned. However, it did lighten John F Kennedy Jr., and he felt insecure, left out, and abandoned.

The crown prince wanted the company of Carolyn Bessette and tried to make her his next best friend in the form of a life partner. He was ready to move on with Carolyn in his life. He wanted to walk his road with Carolyn in every way possible. He knew it was difficult, but he still enjoyed it.

In September, he decided to make her a part of her professional life; with his fiancée Carolyn Bessette, John announced the launch of his glossy magazine George. Sooner than later, JFK Jr. escalated Carolyn from his girlfriend to his fiancée.

The crown prince had to find ways to keep Carolyn committed to him; JFK Jr. knew Carolyn was a very independent and talented woman. So, after dating Carolyn for a year, he was ready to seize every moment in more ways than one.

John F Kennedy Jr. was well-aware of the insecurities of Carolyn Bessette and the type of dilemma she was facing by stepping into Kennedy’s life. JFK Jr. loved Carolyn for what she was - an independent woman with lots of dignity and identity.

John did not want to hurt her, take away her freedom, and make her a part of his life. He wanted to acknowledge the capabilities and talents of Carolyn Bessette.

So, he launched the publication he envisioned would uniquely meld the worlds of politics and celebrity. He could not deny that politics and celebrity life were already inextricably linked, and he thought of publicly acknowledging it.

He knew that Carolyn had experience as a publicist at Calvin Klein, so he knew she could work on this new publication, and it would also give her the financial freedom she feared losing. Moreover, JFK Jr. also found a way to link his life with Carolyn through this magazine.

John F Kennedy Jr got it; Cindy Crawford was dressed as George Washington and photographed by Herb Ritts. The supermodel famously graced the cover of the inaugural edition of the October-November 1995 issue.

"It felt like a victory not just for John, but for Carolyn," Richard Bradley, who served as executive editor at George and went by Richard Blow in those days, quoted in The Kennedy Heirs.