Inside John F. Kennedy Jr.’s Dating History, From Daryl Hannah to Carolyn Bessette
- - Inside John F. Kennedy Jr.’s Dating History, From Daryl Hannah to Carolyn Bessette
Lizz Schumer, Christopher RudolphFebruary 13, 2026 at 7:00 AM
0
John F. Kennedy Jr. and Daryl Hannah, circa 1984 in New York ; John F. Kennedy Jr. and Carolyn Bessette Kennedy attend the Whitney Museum of American Art exhibition of "The Warhol Look" on November 6, 1997 at the Whitney Museum in New York City
Startraks/Shutterstock ; Sonia Moskowitz/Getty
John F. Kennedy Jr. was one of America's most eligible bachelors, whose love life captivated the world
He dated famous women like Daryl Hannah and Madonna before marrying Carolyn Bessette
John and Carolyn's relationship is featured in the new show, Love Story: John F. Kennedy Jr. & Carolyn Bessette
As the only son of President John F. Kennedy and Jacqueline Kennedy Onassis, John F. Kennedy Jr. was considered America's most eligible bachelor, before marrying Carolyn Bessette.
John's love life made headlines, and now his romantic — and ultimately tragic — relationship with Carolyn is chronicled in FX’s Love Story: John F. Kennedy Jr. & Carolyn Bessette.
Love Story is inspired by Elizabeth Beller’s Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, but another book, 2024's JFK Jr.: An Intimate Oral Biography by Liz McNeil and RoseMarie Terenzio, revealed more information about his life and loves through 200 interviews with his inner circle and closest friends.
Here's a look back at John F. Kennedy Jr.'s relationships.
01 of 07
Jenny Christian
JFK Jr and Jenny Christian during graduation at Phillips Academy in Andover
Ron Galella/Ron Galella Collection/Getty
In his senior year, John fell in love with his Andover classmate Jenny Christian, whom his close friend Sasha Chermayeff later called, “the first love of his life, no doubt.”
“He was impressed by her. Because she was so intelligent and funny,” she said in An Intimate Oral Biography about Christian who later went to Harvard.
She remembered Christian typing up a last-minute paper on Lenin and Trotsky.
“She’d sit there for 45 minutes, smoking Larks and then she’d get an A-plus and they would say, ‘Can I keep this to show future students?' "
"[She was] sharp as a tack,” Chermayeff added.
02 of 07
Sally Munro
John F. Kennedy Jr. on August 31, 1980 in Hyannis Port, Massachusetts
Ron Galella Collection via Getty
At Brown University, John fell in love with classmate Sally Munro.
According to John’s friend and Brown classmate Chris Oberbeck who introduced them, “She was a New England, attractive, intelligent girl who came from a big family. She wasn’t trying to be like everybody else.”
John liked her relaxed and warm personality. As Oberbeck put it, “She wore the jeans and the sneakers, not the pleated skirts from New York City.”
03 of 07
Christina Haag
John F Kennedy Jr. and Christina Haag at an event in New York in 1986
Sonia Moskowitz/Getty
After graduation, John took up with another Brown classmate, Christina Haag, with whom he shared a interest for theater and an intense romance.
They had lived together in a group house at Brown but both were dating other people at the time.
When John found out she had broken up with a longtime boyfriend after graduation, John’s close friend, Robbie Littell, recalled in An Intimate Oral Biography, “John ran to the window and yelled out ... ’She’s free, the girl I‘m gonna marry!’ ”
John and Haag started dating while performing in a play together after graduation. They were together for five years and Haag wrote a memoir about their relationship, Come to the Edge, in 2011.
04 of 07
Daryl Hannah
JFK Jr. and Daryl Hannah in New York City in 1994
Startraks/Shutterstock
After Haag, John dated actress Daryl Hannah. He loved her playful side but they had their share of ups and downs.
Amelia Barlow, one of three daughters of John’s close friend, Grateful Dead lyricist John Perry Barlow, had especially warm memories of her.
“I can only tell you what their relationship felt like to me — it felt fantastical, adventurous,” she said in An Intimate Oral Biography. “It felt somewhat young and a little bit maybe naive or immature compared to his relationship with Carolyn. There was a little bit more, like, fire — and fight.”
05 of 07
Madonna
Madonna and JFK Jr. at a public event in Las Vegas in 1997
GTRES/Shutterstock
In the late '80s, John had a fling with Madonna. A friend recounted in An Intimate Oral Biography, “She came on to him and it was flattery."
At the time she was still married to Sean Penn, but their relationship was ending. John and Madonna stayed in touch and years later, he asked her to pose for the cover of his political magazine, George.
“John had this idea of having Madonna pose on the cover as his mom,” Terenzio said. “We would dress her in a suit, her signature sunglasses. And a pillbox hat sitting on a stack of books.”
She turned him down via fax saying, in part, “Dear Johnny boy, Thanks for asking me to be your mother, but I’m afraid, I could never do her justice. My eyebrows aren’t thick enough for one.”
06 of 07
Julie Baker
JFK Jr. and Julie Baker in New York City
Russell Turiak
John met model Julie Baker in 1989.
“I had no idea he even liked me or noticed me,” Baker told the authors. “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.”
A few days later, he invited her to an Andrew Dice Clay show. “We went and we had a blast,” she said.
They dated and remained friends to the end. He had regular lunches with her, right up until the last week of his life.
07 of 07
Carolyn Bessette
John F. Kennedy, Jr. and Carolyn Bessette Kennedy at the annual John F. Kennedy Library Foundation dinner and Profiles in Courage awards May 23, 1999 in Boston, Mass.
Justin Ide/Newsmakers via Getty
It was Carolyn Bessette, whom John met in the early '90s, whom he wooed and married in a storybook wedding on Cumberland Island, Ga., in 1996.
They were both seeing other people when they met but as Chermayeff recalled, “He was obsessed from the minute he met her.” But Carolyn, like Baker, didn’t fall all over him.
One friend, Jack Merrill, has fond memories of meeting her for the first time. “John had been telling me about Carolyn,” he recounted. "This is my new girlfriend and I really like her and she’s gonna come by — and then the chair is empty. He was embarrassed and annoyed. I thought it was hysterical ... I just loved the fact that she was an hour late ... Most girls did not do that to John. She showed up and she sat next to me and we laughed from the minute I first looked at her.”
Their tempestuous romance remained so until their last day, July 16, 1999, when she got on the plane he was piloting to Martha’s Vineyard, to first drop off her sister, Lauren, and then fly to Hyannis Port, where they planned to attend his cousin Rory’s wedding the next day.
“Neither John, nor Carolyn wanted to end their relationship — their goal was to fix what was broken,” Terenzio said.
on People
Source: “AOL Entertainment”
