JFK Jr.’s High-Profile Love Life: A Complete Timeline—Sarah Jessica to Carolyn Bessette
A new doc and TV show put the spotlight back on the late political scion's personal life
America has long been fascinated by political dynasties, and the Kennedy family, in all its power, glamour and tragedy, has an enduring appeal that’s lasted over six decades. President Kennedy’s son, John F. Kennedy Jr., was in the spotlight from childhood, as his father’s funeral took place on his third birthday, and he continued to grow up in the public eye.
In the ’90s, JFK Jr. became a bona fide celebrity, as he was frequently spotted out on the town, and he started George, an of-the-moment magazine about politics and culture, in 1995. The attorney turned publisher’s high-profile relationships were covered breathlessly by the press, and when he married former Calvin Klein publicist Carolyn Bessette in 1996, the charismatic young husband and wife were regarded as the ultimate power couple.
It has now been over 25 years since Kennedy and Bessette’s shocking demise in a 1999 plane crash, and the couple’s mythic status has only grown since then, as stylish pictures of them have become social media mainstays, and American Love Story, a Ryan Murphy series starring Paul Anthony Kelly and Sarah Pidgeon as the couple, has been generating major buzz (not all of it positive) in anticipation of its premiere early next year. On top of all that, CNN just premiered the revealing new docuseries American Prince: JFK Jr.
Given the ongoing cultural obsession with JFK Jr., we’re taking a look back at the women in his too-short life.
JFK Jr.’s first loves and high school romances
The press followed JFK Jr.’s relationships from the time he was a teenager, and in high school, he dated his classmate Meg Azzoni. She went on to become an artist, and later published a book compiling the letters he sent her in the ’70s. Kennedy also dated his classmate Jenny Christian.
While attending Brown University, Kennedy had a six-year relationship with Sally Munro. After they broke up, he dated another Brown classmate, Christina Haag. In 2011, Haag published Come to the Edge, a bestselling memoir about their time together.
The Brooke Shields story—and ‘the best kiss’ she ever had
In the ’80s, Kennedy went on a date with Brooke Shields. Given the fact that Kennedy and Shields had both been famous since childhood, they had a lot in common, but Shields recalled that while they shared “the best kiss I’ve ever had in my life,” she chose not to consummate the relationship, saying, “I really was just so afraid of being really hurt, because if I slept with him I would’ve given him my entire universe, my heart, my everything.”
In 1989, Kennedy began dating model Julie Baker. Looking back on their two-year relationship, she said, “I just loved that he was kind of silly, quirky, forgetful, fun and adventurous.”
Dating in the spotlight: Madonna, Cindy Crawford, Sarah Jessica Parker
Throughout the late ’80s and early ’90s, Kennedy was rumored to have dated glamour girls like Madonna and Cindy Crawford. Crawford later appeared dressed as George Washington on the cover of the first issue of George magazine, and he asked Madonna to dress up as his mom, Jackie Kennedy, for another cover, but she declined.
In 1991, Kennedy started seeing future Sex and the City star Sarah Jessica Parker. Speaking with The New York Times the next year, she quipped, “I never had any idea what real fame was until I met John. He’s a nice man, but for God’s sake, I feel like I should apologize for dating him. It has become the defining factor in the person I am. It’s pathetic. When I die, they are going to say, ‘Oh, yeah, Sarah once dated John Kennedy.’”
Kennedy then dated another blonde actress, Daryl Hannah. He was with Hannah on and off for five years, but their relationship was filled with drama, and Jackie Kennedy reportedly didn’t like the Splash star. They broke up for good after Hannah had Kennedy attend a funeral for her dog (who was killed in a freak accident while he was walking him) while his mom was hospitalized shortly before her death at 64 in 1994.
Meeting Carolyn Bessette and becoming the ’90s It Couple
JFK Jr. and Carolyn Bessette met through her job with Calvin Klein in 1992, when she was working at their VIP fitting room and he was a client. Kennedy came away from this fateful encounter with a variety of suits—and Bessette’s phone number.
With her curtain of glossy blonde hair, sparkling blue eyes and model-esque figure, Bessette was undeniably striking, and she and the tall, dark and handsome Kennedy made for a fairy tale couple. The privileged and stylish pair started dating in 1994, after Kennedy broke up with Hannah, and married in 1996. Bessette-Kennedy’s elegantly minimalist Narciso Rodriguez wedding dress became one of the most influential looks of the era, and after the wedding, her red carpet and street style outfits alike further cemented her status as a fashion icon.
The Kennedys tried to live a somewhat normal life following their marriage, but the paparazzi followed them everywhere, making it impossible for either of them to step out of their swanky New York City apartment without being relentlessly photographed. This constant attention understandably put pressure on their marriage, and Bessette-Kennedy felt particularly stifled by the media’s scrutiny.
By 1999, the Kennedys were seeing a marriage counselor, and according to JFK Jr.’s executive assistant, RoseMarie Terenzio, they were beginning to talk about buying a house outside of New York and starting a family. Sadly, they never got the chance to do any of these things, as they died when the private plane Kennedy was piloting crashed while they were en route to the wedding of his cousin, Rory Kennedy, that same year.
The death of the Kennedys didn’t just send the nation into mourning; it also changed the course of history, as there was much speculation that JFK Jr., who was 38 at the time of his passing, would’ve carried on his family legacy and run for president had he lived.
The countless ’90s photos of JFK Jr. and Carolyn Bessette-Kennedy may be tinged with tragedy, but there’s no denying that they were an eternally compelling couple, and their intoxicating style and chemistry remain unparalleled.
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