From Pop Stars to Hollywood Royalty

Before his untimely death in 1999, John F. Kennedy Jr. (or JFK Jr.), the only son of former President JFK and Jackie Kennedy, was one of the most talked about men in the United States – He was even named People’s Sexiest Man Alive in 1988! So, unsurprisingly, up until his marriage to Carolyn Bassette in 1996, he was one of the most talked-about bachelors too.

And though a man like JFK Jr. could ask out any woman he wanted, the former George magazine editor-in-chief dated a series of gorgeous women in Hollywood throughout his time in the spotlight. “[He’s] a normal, humble, great guy,” said model Julie Baker, who dated the lawyer for two years in the late ’80s.

From a one-time date with Brooke Shields, a six-month relationship with Sarah Jessica Parker or a sweet connection with none other than Material Girl Madonna, JFK Jr. compiled quite an extensive roster of ex-girlfriends.

So, in honor of his impressive list of exes, check out his dating history below!

Meg Azzoni
Kennedy dated artist Meg Azzoni in high school in the ’70s when they both attended Philips Academy. Years after his death, in 2007, Azzoni self-published a series of letters Kennedy once wrote to her in Eleven Letters and a Poem.
Julie Baker
In the ABC documentary The Last Days of JFK Jr, model Julie Baker opened up about her two-year relationship with Kennedy after they met in 1989. “I just loved that he was kind of silly, quirky, forgetful, fun, and adventurous,” she said.
Christina Haag
Actress Christina Haag has opened up about her five-year relationship with Kennedy in the past. “We were together for the next five and a half years, as he studied law at N.Y.U. and began at the Manhattan D.A.’s office, and I performed in plays and acted in television and independent films,” she wrote in her book Come to the Edge.
“Our apartments were blocks away from each other on the Upper West Side, we spent weekends at his mother’s houses in New Jersey, Martha’s Vineyard, and Hyannis Port, and during the summers of 1987 and 1988, we lived together in Washington, D.C., and Venice, California. We also loved to travel. And in the early spring of 1989, we took a trip to a place neither of us had been before—Treasure Beach, on the remote southern coast of Jamaica.”
Madonna
In 1988, in addition to being named People’s Sexiest Man Alive, Kennedy also began an affair with Madonna during his relationship with Haag.
“The only place the superstar couple could let their guard down was in Hyannis Port, where they bundled up in sweaters and jackets and jogged on the beach,” Christopher Anderson wrote in his book The Good Son: JFK Jr. and the Mother He Loved, “Inside the compound, they curled up by the fire, sipping daiquiris from Waterford crystal glasses.”
The two eventually broke things off because his mother Jackie didn’t approve.
Cindy Crawford
Model Cindy Crawford and Kennedy were rumored to have dated back in 1995. The two first met after Crawford graced the first-ever cover of Kennedy’s magazine, George.
Daryl Hannah
Kennedy also dated model and actress Daryl Hannah. The two were non-exclusive for four years until they took the extra step to become exclusive in 1992 after Hannah broke up with her boyfriend, singer Jackson Browne.
The two called it quits two years later in 1994 a few months after the passing of his mom, Jackie Kennedy. According to Steven M. Gillon’s recent biography America’s Reluctant Prince: The Life of John F. Kennedy Jr., per InStyle, they split because Hannah was more interested in talking about her sick dog than being there for Kennedy in the challenging time. “Can you believe this?” Kennedy reportedly told his friend at the time, “I just lost my mom and all she wants to talk about is her sick dog.”
Sarah Jessica Parker
Sex and the City‘s Sarah Jessica Parker dated Kennedy from 1991 to 1992. During their six-month relationship, Kennedy gave her a crash course on being famous.
“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,” she told the New York Times in 1992. “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.'”
In 2017, Parker was asked about Kennedy once again during an episode of Watch What Happens Live. In addition to saying kissing him was “pleasant,” Parker said his hair was “exquisite.”
Xuxa
Brazilian TV presenter Xuxa once opened up about going on a date with Kennedy. “I thought he was a very handsome guy and I wanted to meet him,” she said in her documentary, per Vogue Brazil. “He rode a bike, I thought it was the cutest thing. And then I went out to dinner and I didn’t feel like eating anything with that god in front of me.”
During the date, the two went for a walk and paparazzi were everywhere. After the pictures were published, Kennedy was told Xuxa was the one that authorized it and never reached out to her again. “I spoke to him, we scheduled him to come to Brazil, but soon after this article came out and he never called again,” she said.
Brooke Shields
Earlier this year, Brooke Shields dished on her somewhat awkward date with Kennedy at The Howard Stern Show, per People. “He kissed me, and it was like the best kiss I’ve ever had in my life,” Shields remembered. “It was beyond not-disappointing. The lips are beautiful, and the face is amazing, and the body and the person, and he was down to earth and funny and irreverent.”
After the kiss, however, Kennedy wanted to move to the next step while Shields just “froze.” “I had to get a cab home, which was a little less chivalrous,” Shields said, adding that he didn’t look or talk to her the next day. “On the one hand, I was like, ‘S—!’ On the other hand, I was like, ‘Thank God … he showed his true colors,'” she said.
Carolyn Bessette
In 1996, Kennedy settled down as he tied the knot with Calvin Klein publicist Carolyn Bessette. Their short-lived marriage, which ended with their tragic plane crash in 1999, was filled with tabloid speculation and media attention.
In 1996, for example, the National Enquirer witnessed a fight between the two at Washington Square Park in New York City, per E! Online. Although the moment became infamous, the two were reportedly working on getting their marriage back on track before their passing.