John f kennedy jr dating history carolyn bessette daryl hannah madonna 20260216 p5o8uo.html – Breaking News & Latest Updates 2026
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This was published 6 months ago

The famous women John F Kennedy, Jr dated before he fell for Carolyn Bessette

Kahla Preston
Kahla Preston

It's been 27 years since his tragic death, but all of a sudden everyone's talking about John F. Kennedy, Jr again.

The late son of John F. and Jackie Kennedy has been thrust back into the spotlight by a new Ryan Murphy-helmed TV series reliving his romance with Carolyn Bessette.

Watch the video above.

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The couple, alongside the Calvin Klein publicist's sister Lauren Bessette, were killed in a plane crash in 1999.

John F. Kennedy Jr. and Carolyn Bessette

John F. Kennedy, Jr and Carolyn Bessette are back in the spotlight thanks to a new TV series, Love Story. WireImage

Love Story: John F. Kennedy, Jr and Carolyn Bessette is focused on the titular couple, but it also touches on one of Kennedy's famous exes: actress Daryl Hannah, portrayed by Dree Hemingway.

Before he met Bessette, JFK Jr was linked to a number of famous women, from Madonna to Sarah Jessica Parker and even, very briefly, Brooke Shields.

However, it was his romance with Hannah – which ended not long before he and Bessette became serious – that drew particular tabloid interest.

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Daryl Hannah with John F. Kennedy Jr. at Edward Kennedy Jr.'s wedding on Block Island, Rhode Island, 1993.

The Kennedy heir's romance with actress Daryl Hannah is also featured in the Ryan Murphy-helmed show. Getty

Let's take a look back at the late magazine publisher and attorney's dating history before he said "I do".

The student years

During his student days, JFK Jr had two major relationships.

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As a high schooler at Phillips Academy in Andover, he struck up a romance with classmate Jenny Christian.

John F. Kennedy Jr. and Jeannie Christian (or Jenny Christian) during his graduation from Phillips Academy in Andover, Massachusetts, United States in 1979.

John F. Kennedy Jr. with Jenny Christian) at his graduation from Phillips Academy in 1979.  Ron Galella Collection via Getty

A friend of Kennedy once described Christian as "the first love of his life, no doubt."

Later, at Brown University, he dated fellow student Sally Munro for six years.

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Christina Haag

In 1985 he began dating actress Christina Haag, who has appeared in TV series including Law and Order, Criminal Minds and Heroes.

The pair had met as teenagers and both attended Brown University, even living together in a group house, but they were dating other people at the time.

Things finally turned romantic when they starred in a play together in their mid-20s, and the relationship lasted five years.

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Haag wrote about her relationship with Kennedy in her 2011 book Come to the Edge; when discussing why it ended, she said, "We were young."

Madonna

It's been reported Kennedy and pop icon Madonna dated for six months in the late '80s, but other reports suggest it was merely a flirtation and nothing more.

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"They would try to get together but it was hard because she was on tour and he was working," a friend of Kennedy's told People.

"They saw each other a few times and they had a flirty and friendly banter but it wasn't a 'relationship.'"

Madonna at Herb Ritts Birthday Party in Los Angeles, California, 1989

Madonna, pictured in 1989, was romantically linked to Kennedy in the late '80s. WireImage

Sarah Jessica Parker

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JFK Jr dated Sarah Jessica Parker for six months in 1991-92, a period the actress later referred to as "the Kennedy fiasco".

The Sex and the City star said the relationship invited a level of public attention she'd never before experienced.

"I never had any idea what real fame was until I met John," she told the New York Times.

"He's a nice man, but for God's sake, I feel like I should apologise for dating him. It has become the defining factor in the person I am.

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"When I die, they are going to say, 'Oh, yeah, Sarah once dated John Kennedy.'"

Daryl Hannah

Kennedy's most significant celebrity love interest was actress Daryl Hannah, with whom he had an on-and-off relationship for five years starting in the late '80s.

The book JFK Jr.: An Intimate Oral Biography claimed it was a "volatile" relationship that began when they were in relationships with other people.

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They ultimately broke up in 1994, not long after the death of Jackie Kennedy Onassis – and shortly before Kennedy and Bessette's love story began.

Love Story echoes the claim a final nail in the coffin for the couple was the accidental death of Hannah's dog while Kennedy was walking it in New York in 1994.

The book claimed the actress tasked Kennedy with transporting the ashes to LA for the funeral.

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At the time, his mother's health was taking a turn in New York, and she died days later.

"He was deeply resentful that Daryl dragged him out there to attend a funeral for her dog when his mother was dying of cancer," a friend of Kennedy was quoted as saying.

There are also claims of a strained relationship between the Hollywood star and Kennedy Onassis, though this has also been refuted.

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"The character 'Daryl Hannah' portrayed in the series is not even a remotely accurate representation of my life, my conduct or my relationship with John," Hannah said in a New York Times essay after the "tragedy-exploiting" show's release.

"I have never pressured anyone into marriage. I have never desecrated any family heirloom or intruded upon anyone's private memorial ... I have never planted any story in the press. I never compared Jacqueline Onassis' death to a dog's.

JFK Jr. and Daryl Hannah   (Photo by Mitchell Gerber/Corbis/VCG via Getty Images)

Hannah called the series "tragedy-exploiting" and said it's not a "remotely accurate" representation of her. Corbis/VCG via Getty Images

Carolyn Bessette

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During his relationship with Hannah, Kennedy met the woman who'd one day be his wife.

He reportedly encountered Carolyn Bessette for the first time in 1992 in the VIP fitting room at Calvin Klein, where she was assisting VIP customers. Both were dating other people at the time.

Carolyn Bessette and John F. Kennedy Jr.

Kennedy married Carolyn Bessette, whom he'd met through her work at Calvin Klein, in 1996. Getty

They began dating in 1994, and despite the rampant media interest in the romance, the couple managed to marry in secret in 1996.

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Their story was cut cruelly short in July 1999 when they were flying to Martha's Vineyard for a family wedding with Bessette Kennedy's sister, Lauren Bessette.

Piloting the single-engine aircraft, Kennedy departed New Jersey at 8:38pm but lost control of the plane over the Atlantic Ocean an hour later. All three died in the crash.

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