All The Women JFK Jr. Dated Before Marrying Carolyn

John F. Kennedy Jr. was linked to plenty of women throughout his life, leading some to believe he had a reputation similar to his father's. However, JFK Jr. worked hard to separate himself from his father's well-known "womanizer" status, at least according to those close to him.

JFK Jr.'s close friend John Perry Barlow explained on the SPIKE TV documentary "I Am JFK Jr.," that he felt President Kennedy's infidelity may have just been the reason why JFK Jr. felt the need to fit the image of a good man. "He called me once and said, 'It seems like it would be a cakewalk for me because everyone expects me to be a great man,'" Barlow quoted Kennedy. "'But it does seem to me,'" Kennedy continued, "'as I read these biographies of great men through history, they were not particularly great at home. Even my father was no model — and I think it would be a much more interesting challenge to see if I could make myself into a good man'" (via People).

Although, according to Barlow, what Kennedy meant by this is up to interpretation, but he feels that it was about fidelity — something Barlow believes JFK Jr. was very keen on despite his reputation. It was Carolyn Bessette who ultimately gave him the opportunity to show his loyalty, but before meeting her, Kennedy was involved with a number of different ladies. Here, we're taking a closer look at all of the women who had their turn at dating "America's Prince."

Brooke Shields has been in the public eye since she was only 11 months old, but it was her popular film roles and commercials in the 1980s that made her an icon of the era. However, little did audiences know at the time, Shields was privately crushing on JFK Jr. since early childhood. "I was so madly in love with him since the time I was three," she said of Kennedy on the "The Howard Stern Show" in 2023. Fast-forward a few decades later, and Shields finally had the opportunity to meet Kennedy in person.

The two met on a skiing trip in Aspen, Colorado, where Shields was vacationing with her mother and where the Kennedy family was staying. Upon trying to impress Kennedy on the ski slopes, Shields fell into some nearby trees — which she needed to be lifted out from — but despite her mishap, the pair got to talking. "He kept saying I look like his mother," said Shields. "Which is really interesting, and a compliment, but it was also like, 'I don't know how to feel about this.' And then we did have a real date."

However, the date was not exactly what Shields was expecting. Kennedy invited her to a loud and rowdy bar, so the pair were swift to make an exit. They went back to Kennedy's hotel, where Shields claims he tried to make a sexual advance, which she declined out of fear that he wouldn't talk to her again afterwards. Kennedy never spoke to Shields again after the rejection, but in the end, she was glad she got to see his "true colors" that night.

Before Sarah Jessica Parker was captivating audiences as Carrie Bradshaw, she was an '80s film star — a film star who was in a relationship with Robert Downey Jr. at the peak of his addiction. When the '90s hit, Parker seemingly had enough of Downey when he wasn't able to get it together. As Downey put it in a 2008 Parade interview, "I liked to drink, and I had a drug problem, and that didn't jibe with Sarah Jessica, because it is the furthest thing from what she is" (via People). So, when Parker met JFK Jr. shortly after her relationship with Downey ended, the public was happy for her. JFK Jr. was, at the time, the closest thing the United States had to royalty, and America's prince seemed like the perfect fit for the '80s sweetheart.

Apparently, the duo met at a theater in 1991, and Parker's close friend Adam Shankman can recall the exact day Kennedy made his move. "She called me, screaming, 'You're not going to believe who asked me out!'" Shankman told People back in 2000. Unfortunately, Parker's excitement didn't last very long. The duo only lasted six months, and by the following year, she began declaring her time with JFK Jr. as "the Kennedy fiasco." She blamed this on Kennedy's immense level of fame, telling The New York Times, "We would go places where there wasn't a soul around, and the next day I'd see pictures of us there in the tabloids" (via InStyle). "I have been a semi-public person since [starring in 'Annie' on Broadway as a child], but I never had any idea what real fame was until I met John."

Many women who dated JFK Jr. have kept most of the details about their days dating the only son of JFK rather private. However, in 2019, ABC released a documentary titled "The Last Days of JFK Jr.," where several ex-lovers had the opportunity to speak about the late JFK Jr. for the first time since his death in 1999. According to the Boston Globe, ABC had announced prior to the documentary's release that it would feature an exploration of "not only John's life, but also the stressors that he was facing in his final days, from apparent turmoil in his marriage to keeping his magazine George afloat."

One of the women who stepped forward in the documentary was Julie Baker, a model whom JFK Jr. met in 1989 and dated until 1991. The couple had their first date at an Andrew Dice Clay stand-up performance, and as Baker says in the documentary, JFK Jr. was just "a normal, humble, great guy" (via Town & Country). She further described her relationship with JFK Jr. by explaining that she "just loved that he was kind of silly, quirky, forgetful, fun, and adventurous." 

Even though the pair split and Kennedy went on to marry Carolyn Bessette, it's been alluded that he remained close with Baker and supposedly had several sexual encounters with her while he was married. But according to Kennedy's close friend Sasha Chermayeff, JFK Jr. was "very serious, and very seriously committed to the fact that he had fallen madly in love with Carolyn" (via Vanity Fair).

It's difficult to mention pop culture icons of the 1980s without the name Madonna passing through our lips, so it was only natural that the "Material Girl" herself was found in the likes of JFK Jr. Although reports are conflicted on just how involved the famous pair actually were, what is agreed upon is that the two met at a party in 1985 after one of Madonna's concerts at Madison Square Garden. From there, the two kept their meetings hush-hush, but they could sometimes be seen jogging together through Central Park or going to the gym. As one of Kennedy's close friends told People, "They saw each other a few times and they had a flirty and friendly banter but it wasn't a 'relationship.'" The source also noted, "They would try to get together but it was hard because she was on tour and he was working."

On the other hand, it's also been reported that JFK Jr.'s mother, Jackie Kennedy, wasn't very keen on Madonna as a match for her son. While one might easily correlate Madonna with Marilyn Monroe — who President Kennedy had an alleged affair with — the issue in the former First Lady's eyes had more to do with the fact that Madonna, although separated, was still legally married to Sean Penn. Moreover, "Jackie had spent her entire celebrity life avoiding paparazzi, whereas Madonna would court paparazzi. And Jackie just couldn't understand any of that," biographer J. Randy Taraborrelli explained to People. Despite Jackie's objections, her son casually dated Madonna for six months.

A breakout star of the '80s, Daryl Hannah made a name for herself in films like "Blade Runner," "Splash," and "Steel Magnolias." Hannah originally met Kennedy in the early '80s when both of their families were vacationing in Saint Martin, and it was Hannah's quirkiness that initially captured Kennedy's attention. "John found it odd that Daryl seemed to carry a teddy bear with her wherever she went, but also found her fascinating," biographer Steven M. Gillon wrote in his book, "America's Reluctant Prince: The Life of John F. Kennedy Jr." (via InStyle). The pair didn't meet again until a wedding in 1988, but this time around, they started dating. For the next six years, Kennedy and Hannah were off and on again until they decided to call it quits in 1994.

As far as what caused the final straw, Gillon told InStyle that while Jackie Kennedy was in a New York hospital just days before her death, John was stuck in L.A. for Hannah's dog's funeral. "And even after [Jackie] died," Gillon explained, "Daryl had another dog that was sick and John was up in Martha's Vineyard or Hyannis Port, and Daryl's on the phone talking about her dog all the time and John is there in the kitchen with [his longtime friend] Sasha Chermayeff, and he says, 'Can you believe this. I just lost my mom and all she wants to talk about is her sick dog.'"

Though Hannah moved on and eventually married singer/songwriter Neil Young in 2018, she allegedly has never recovered from Kennedy's death, one source reported to OK!.

Whether "America's Prince" and England's former princess ever had an affair is up for debate, but what we can confirm is that the two pulled off a secret meeting in the summer of 1995. Kennedy wanted Princess Diana to pose for the cover of his magazine, George, and he invited her to New York in hopes of convincing her to do the shoot.

"We had to draw all these cover ideas up, and he took the drawings over to the Carlyle Hotel to meet her," Matt Berman, George magazine creative director, shared with People in 2017. To pull off the meeting, someone suggested Kennedy arrive at the hotel in disguise, and because the press was expecting the famous pair to walk in the side door, Kennedy and Princess Diana were able to sneak through the front door undetected. The two spoke for about an hour and a half in Diana's suite, but she ultimately ended up declining the shoot.

However, Simone Simmons, Princess Diana's former energy healer, claimed in her book, "Diana: The Last Word," that the story had gone quite differently. Alleging that the Carlyle Hotel is where President Kennedy and Marilyn Monroe would meet for private rendez-vous, Simmons also insists that JFK Jr. and Princess Diana's meeting was "a moment of pure lust." "We started talking, one thing led to another — and we ended up in bed together. It was pure chemistry," Simmons claims Diana told her. Other sources close to Diana called the allegation completely false.

Out of all of JFK Jr. 's flames prior to meeting Carolyn Bessette, Christina Haag was notably the most serious and most consistent. In fact, Haag had so much to say about the youngest Kennedy child that she wrote an entire memoir dedicated to their relationship called "Come to the Edge." The couple originally met as teenagers and attended college together, where they bonded over a love of theater and acting. After graduation, they were both cast in the same play and began dating. In her memoir, Haag highlighted how Kennedy was just a normal, regular teen who liked to play pranks, smoke marijuana, and refer to Jackie Kennedy as "mummy."

Haag cites being "young" as the reason why she and Kennedy broke up after five years together. Years down the road, when she heard about Kennedy's engagement to Bessette, Haag, admittedly, shed a few tears. "I felt, even though things were over, there's a wistfulness," she wrote. "There's a sense of, 'Oh, this is a real ending.' And at the same time, I was proud of him. Because he was able to make that choice, and I felt that — I felt happy that he was able to find someone that he wanted to spend his life with."