JFK Jr. & Carolyn Kennedy: A Look At Their Heartbreaking Love Story

America might not have a royal family, but back in the 1990s, the Kennedys came pretty close. John F. Kennedy was, of course, the hugely popular President from 1961 until his assassination in 1963. His son, John F. Kennedy Jr., went on to become a well-known personality in New York City in the '90s. In fact, in 1988, he was named the "Sexiest Man Alive" by People. You may even remember that episode of "Seinfeld" when Elaine almost got a date with the famous bachelor. Although JFK Jr. was one of New York City's most sought-after bachelors, when he met Carolyn Bessette, all of that changed.

Before meeting JFK Jr., Bessette was an up-and-coming New York personality in her own right with a prominent job at Calvin Klein. The pair met in 1992 and tied the knot in 1996. They quickly became one of the tabloids' favorite couples and they were hounded by paparazzi throughout their marriage. In addition to the strain of the press, the couple was also dealing with a number of other pressures. According to reports, they were trying to work through their issues when their lives were tragically cut short in a plane crash in 1999. 

Carolyn Bessette met JFK Jr. while working at Calvin Klein

Carolyn Bessette and John F. Kennedy Jr. first met in 1992, and there are a few different stories about the couple's meet-cute. According to Vanity Fair, some believe they locked eyes while jogging in Central Park. However, chances are, they were actually introduced by Kelly Klein, an artist and ex-wife of Calvin Klein. Either way, friends say it was practically love at first sight. "John loved Carolyn, he was enchanted with her — body and soul — from the first minute he met her," said JFK Jr.'s friend Brian Steel (via Yahoo!).

At the time, Bessette had a job in Calvin Klein's PR department and was quickly becoming known for her timeless, chic style. Ralph Lauren allegedly once told his team: "Every time you design something think of Carolyn Bessette" (via Harper's Bazaar). As for JFK Jr., he was allegedly still dating actress Daryl Hannah when he first met Bessette.

The pair started dating in 1994

By 1994, it seemed that John F. Kennedy Jr. and Carolyn Bessette's relationship had turned romantic. In the early days of their relationship, it wasn't always smooth sailing. According to JFK Jr.'s friend, Brian Steel, who was interviewed for the documentary "The Last Days of JFK Jr.," Bessette was a little flaky at first. "Early on, he would be frustrated," said Steel (via Yahoo!). "He would say, 'I called her and she hasn't called me back.' And John did not like that." 

In fact, according to another friend, Gustavo Paredes, Bessette initially declined a date with JFK Jr. "She didn't think he was serious," Paredes told People. "He couldn't believe she turned him down. It had never happened before." JFK Jr. allegedly persevered by coming to visit Bessette at work to prove her wrong.

According to RoseMarie Terenzio, the personal assistant of JFK Jr. and the author of a biography about the couple called "Fairy Tale Interrupted," Bessette was the perfect match for JKF Jr. "She was exactly the kind of girl I imagined would date someone like John Kennedy Jr., and she intimidated the hell out of me," the author wrote (via Yahoo!).

JFK Jr. and Carolyn Bessette became secretly engaged

After falling in love with Carolyn Bessette, it wasn't long before John F. Kennedy Jr. popped the question. He allegedly asked her to marry him in July 1995. The pair were spending a quiet weekend on Martha's Vineyard and were on a boat ride at the time. "He went into this thing about how everything's better with a partner, not just fishing but life," author RoseMarie Terenzio said to People. "He said, 'I want you to be my partner.'"

Even though JFK Jr. was practically American royalty, Bessette wasn't initially convinced that getting married was a good idea, so she took some time to think things over. As Terenzio wrote in her book, "Fairy Tale Interrupted" (via Yahoo!), Bessette "worried marriage would change everything" — especially when it came to her privacy. "She understood that the formality meant something, especially to John and his lifestyle," wrote Terenzio. Around three weeks after his romantic proposal, she finally accepted and the pair became secretly engaged.

The pair were filmed having a huge argument

As the press found out about John F. Kennedy Jr. and Carolyn Bessette's relationship, they began to follow them around New York City hoping for candid photos of the couple. Unfortunately, this meant that private moments between the couple became public. In 1996, the pair were filmed by paparazzi having a massive argument in Central Park (via YouTube). The incident was so widely publicized that it took up eight pages in the New York Daily News at the time.

Apparently, the fight began after Carolyn had deduced that a mutual friend was trying to use her fiancé as clout — and that JFK Jr. was letting it happen. "The cause of this infamous fight, and the many that followed, stemmed from Carolyn's ongoing complaint that John let people walk all over him," wrote JFK Jr.'s friend, Steven M. Gillon, in his book "America's Reluctant Prince: The Life of John F. Kennedy Jr." (via InStyle).

Even though the fight looked pretty serious, according to Gillon, it was actually a healthy part of their relationship. "Carolyn, more than anyone who John had been with, would stand up to him, and confront him, and I think that John to an extent needed that," Gillon said. Another friend, Ariel Paredes, described them as "fiery." (via People). "They would love hard and they would fight hard but they were very much a couple," Paredes said.

They married in 1996 on an island

Despite their tumultuous relationship, John F. Kennedy Jr. and Carolyn Bessette tied the knot in a private ceremony on Cumberland Island in Georgia in 1996. Apparently, the small wedding was kept so under wraps that the papers (and some family members) didn't know until the next day. As the couple's friend, Carole Radziwill, wrote for the Daily Mail: "There were wild horses and wildflowers, it was untouched and bucolic. That night there was a wedding — one of the best-kept secrets of modern time. It was the most famous wedding of the year, the decade. ... And no one but the thirty-two close friends and family who arrived, knew." Apparently, guests were asked to show a nickel as a sign that they were invited to the exclusive event.

Bessette wore a dress by designer, Narciso Rodriguez, along with her famous red lipstick. Even though Rodriguez made the dress for his friend, when a picture of the wedding made it to the front pages, he became a "very public person overnight," as he put it (via YouTube). The couple couldn't have been happier. 

In a documentary entitled "JFK Jr. and Carolyn's Wedding: The Lost Tapes," Sasha Chermayeff, an old friend, commented on the intimate, romantic nature of the wedding. "They wanted something that really felt real to them," she said (via YouTube). "It was really beautiful, 'cause they just wanted to dance together. It wasn't an exhibition, it was something that really had, you know, meaning."

The pair appeared before the press when JFK Jr. asked for privacy

After their private intimate wedding, John F. Kennedy Jr. and Carolyn Bessette prepared for their new life as a married couple. The first step they took after their honeymoon was to make an appeal to the press — after being hounded by paparazzi, they decided to ask for privacy. 

First, JFK Jr. appeared on the front steps of the couple's apartment in Tribeca, where he said: "I just ask [for] any privacy or room you could give her as she makes that adjustment. It would be greatly appreciated." He then reappeared with his new wife. The couple then stepped into their waiting car and drove off. 

It's clear the pair knew that the press would be more invasive than ever after the wedding. But even though JFK Jr. made a touching appeal on behalf of Bessette, things only got worse.

The press scrutiny became out of control

After John F. Kennedy Jr. and Carolyn Bessette tied the knot, the media became more and more interested in the couple. They began following them everywhere they went. For Bessette, the attention became more and more intrusive. What made things worse was the fact that the couple didn't have their own security detail. As RoseMarie Terenzio told People, this had been JFK Jr.'s idea. "John wasn't sensitive to the fact that this had been his life since he was born, but it was not Carolyn's," Terenzio explained. Apparently, their lack of protection made Bessette even more "uneasy." 

"Carolyn was a very sophisticated woman who knew exactly what she was getting into, but it was still difficult to handle at first," Mitchell Fink, an acquaintance of Bessette told The Guardian. "It offended her that her privacy was being intruded on that level." As the publication reported, the more she clung to her privacy, the more the media seemed to turn on her.

As Stephen M. Gillon told Town & Country, the media scrutiny changed Bessette. "The paparazzi treated her horribly. ... She went from being this vivacious and energetic person, and now she feels captive."

The couple had their fair share of tragedies to deal with

Life for the newlyweds wasn't all easy. In addition to the press scrutiny, they were also dealing with personal tragedies. For one thing, John F. Kennedy Jr.'s close friend and cousin Anthony Radziwill had been diagnosed with sarcoma, a type of bone cancer. Anthony and his wife Carole had become extremely close with Kennedy and Bessette. By 1999, it became clear that his illness was terminal. 

"That was a very painful year [for him], to watch someone he'd grown up with, who was exactly his age, and he's dying and it's really hard on his wife, his sister, his mother," Sasha Chermayeff, an old high school friend of JFK Jr., told Town & Country. "For John, I think that Anthony's illness brought everybody closer in a good way, including Carolyn and him."

As Carole Radziwill later recalled in an article for the Daily Mail, Bessette helped everyone stay positive during Anthony's illness. "Carolyn was the glue who kept people together," she wrote. "Specifically, that summer, the four of us in a difficult time."

The couple spent their time visiting restaurants, walking their dog, and seeing friends in New York City

Despite the media attention and the fiery nature of their relationship, Carolyn Bessette and John F. Kennedy Jr.'s relationship had its high points — though these weren't as interesting to the tabloids. They spent most of their time living a quiet, normal life in New York City. The pair shared an apartment in Tribeca and were frequently spotted out and about walking their dog. They were also often seen at local museums, galleries, and restaurants like the Whitney Museum, Rao's restaurant, Area Nightclub, and Bubby's restaurant in Tribeca. According to Town & Country, JFK Jr. wanted to be seen as a normal New Yorker.

Of course, because of the paparazzi, the couple also stayed inside a lot. "A lot of times we wouldn't leave," recalled their close friend, Carole Radziwill (via Vanity Fair). "We would order foods from Bubby's on the corner. Who wanted to leave and have to go walk through that? That was, like, every day of her life for the first year or more."

The couple began to disagree after around three years

Problems started between John F. Kennedy Jr. and Carolyn Bessette after around three years of marriage. According to a number of reports, one of their biggest disagreements centered around children. "I want to have kids, but whenever I raise the subject with Carolyn, she turns away and refuses to have sex with me," JFK Jr. reportedly complained to a friend in 1999 (via Vanity Fair). As for Bessette, she allegedly told a friend: "I hate living in a fishbowl. John may be comfortable living like this, but I'm not. How could I bring a child into this kind of world?"

According to one friend, the slight age gap between the pair might have contributed to their disagreements. After all, JFK Jr. was six years old than Bessette, and he may have been ready to start a family before she was. Other reports claim that Bessette was eager to find a more private home away from New York City before they had any children.

In 1999, as the arguments escalated, the pair decided to see a marriage counselor. According to "The Kennedy Heirs" author, J. Randy Taraborrelli: "John didn't want to be one of those Kennedy men who didn't care how his wife feels" (via Irish Central).

The couple reportedly turned to drug use as life became more stressful

Although John F. Kennedy Jr. and Carolyn Bessette's marriage was filled with happy moments, the pressures of life in the spotlight did sometimes become difficult to bear. According to some reports, the couple occasionally turned to drugs when things got hard to handle. It was also simply a way to let loose. 

"This was the nineties when young people, like John and Carolyn, sometimes partied. They had experiences the way people often do. I found no evidence of any addiction or problems for either of them," wrote J. Randy Taraborrelli (via Irish Central). For JFK Jr., drugs offered "a way of experiencing life differently." 

Apparently, one friend saw the pair doing cocaine. "It's been a bad week ... Look I'm a Kennedy," JFK Jr. reportedly said (via Page Six). "Do you think this is the first time I've done drugs? Please." According to another friend, Bessette's drug use did begin to become problematic. "She and I went to dinner one night when John was sick at home with the flu. She made at least a half-dozen trips to the bathroom and came back to the table with white rings around her nostrils," the friend told Vanity Fair. Eventually, when the couple began seeing a marriage counselor, Bessette was said to have refused to speak about her drug use in the sessions.

Carolyn Bessette allegedly kissed an old friend

The marriage between Carolyn Bessette and John F. Kennedy Jr. became more and more fraught in the late '90s. According to "The Kennedy Heirs," a biography of the famous couple by J. Randy Taraborrelli, Bessette ended up kissing an old friend in 1998 after her marriage became more complicated. After the kiss, she allegedly "pulled away and said, 'No, what am I doing? I can't be here right now,' and quickly left." The book goes on to allege that when JFK Jr. found out about the kiss from his wife, he showed up at the friend's house and punched him, saying: "Stay away from my goddamn wife." 

JFK Jr., on the other hand, reportedly never cheated on Bessette, even after her kiss. In the biography "America's Reluctant Prince: The Life of John F. Kennedy Jr.," author Stephen M. Gillon claimed: "It appears unlikely that John was having an affair. He confessed to friends, 'I wish I could cheat on her'" (via YouTube). However, JFK Jr. was apparently wary of following in his father's footsteps.

JFK Jr. and Carolyn Bessette died together in a plane crash

Tragedy struck in 1999 when John F. Kennedy Jr. and Carolyn Bessette were killed in a plane crash on July 16. JFK Jr., who had been taking flying lessons, had decided to fly his plane from New Jersey to Martha's Vineyard with Bessette and her sister, Lauren. Although he usually flew with an instructor, he decided to fly alone on this occasion. The plane crashed into the Atlantic Ocean in an accident that was later attributed to poor conditions and pilot error. As his old friend, Sasha Chermayeff, told Town & Country: "He wasn't fully instrument trained; he shouldn't have done it. It was a pilot negligent mistake in which he died and two people died with him."

At the time, Bessette's mother released a statement that read: "The loss of these three young people whom we loved so much has forever changed our lives. We continue to struggle with our grief, and we choose to maintain what's left of our privacy."