Before his marriage to Carolyn Bessette — and their tragic deaths — John F. Kennedy Jr. made headlines for his dating life.
John F. Kennedy and Jackie Kennedy‘s son was in the public eye since he was a child. By the time he was an adult, JFK Jr. worked as an assistant district attorney in Manhattan before launching his own magazine.
In his personal life, JFK Jr. was linked to high-profile models such as Brooke Shields and Cindy Crawford — as well as actress Sarah Jessica Parker. He dated Daryl Hannah, but they ultimately called it quits and JFK Jr. found love with Bessette.
JFK Jr. and Bessette met in the early 1990s and got married in 1996. They died three years later in 1999 in a plane crash off the coast of Hyannis Port, Massachusetts. Their romance — and JFK Jr. as a public figure — is the subject of FX’s limited series Love Story.
How the ‘Love Story’ Cast Compares to Real Members of the Kennedy Family
Keep scrolling to relive JFK Jr.’s dating and marriage history.
Jenny Christian
After meeting in high school, Jenny Christian and John F. Kennedy Jr. dated from 1978 to 1979. Christian, who attended Phillips Academy Andover with JFK Jr., was his first serious girlfriend.
Sally Munro
John F. Kennedy Jr. crossed paths with Sally Munro in 1979 while they were both at Brown University. They dated for six years before calling it quits.
Brooke Shields
While at Brown, John F. Kennedy Jr. and Brooke Shields initially met and they were later linked in the ’80s.
“He kept saying I looked like his mother, which was really interesting and a compliment, [but] I also was like, ‘I don’t know how to feel about this,’” Shields shared on The Howard Stern Show in 2023. “And then we did have a real date. And I wouldn’t sleep with him because I kind of loved him too much.”
Shields referred to her kiss with JFK Jr. as the best she’s “ever had,” adding, “It was beyond not-disappointing. … I froze though because he was so precious to me. I was like, ‘Oh, my God, you’re falling in love, and if you sleep with him he may not talk to you again — and you can’t handle that.’ I wasn’t playing a game. 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.”
Christina Haag
After graduating from university, John F. Kennedy Jr. started dating former classmate Christina Haag. They were together for five years and Haag wrote a memoir about their relationship titled Come to the Edge.
Madonna
During a break from his romance with Christina Haag, John F. Kennedy Jr. sparked romance rumors with Madonna, who was going through a separation from Sean Penn.
Julie Baker
John F. Kennedy Jr. met model Julie Baker in 1989. They went on to date off and on before pulling the plug on their relationship in 1991.
“I had no idea he even liked me or noticed me,” Baker shared in an interview for the 2024 book JFK Jr.: An Intimate Oral Biography by Liz McNeil and RoseMarie Terenzio. “And less than a week later, he called me up … I was actually surprised to hear from him. He asked if I wanted to go to a poetry reading. And I was like, no. You know, to me that sounded so boring. It didn’t matter that it was John.”
They remained friends even after their breakup — and Baker saw JFK Jr. one week before his death.
JFK Jr. and Carolyn Bessette-Kennedy’s Relationship Timeline
Sarah Jessica Parker
John F. Kennedy Jr. and Sarah Jessica Parker dated for six months between 1991 and 1992 before parting ways due to the public interest surrounding their relationship.
Cindy Crawford
In 1995, John F. Kennedy Jr. was rumored to have dated supermodel Cindy Crawford shortly after her divorce from Richard Gere.
Daryl Hannah
John F. Kennedy Jr. was in a serious relationship with actress Daryl Hannah, whom he had known since the 1980s. After meeting again at his aunt Lee Radziwill’s wedding in 1988, JFK Jr. and Hannah dated for five years.
Carolyn Bessette
John F. Kennedy Jr. met Carolyn Bessette when he was still with Daryl Hannah. In the early ’90s, the couple got engaged and married in 1996. Despite struggling with their marriage being such a topic of discussion, JFK Jr. and Bessette were working on their relationship at the time of their deaths in 1999.
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