Inside John F. Kennedy Jr.'s star-studded dating history before Carolyn Bessette: from Daryl Hannah to Sarah Jessica Parker


In Ryan Murphy's Love Story, JFK Jr. was played by Paul Anthony Kelly, while his eventual wife Carolyn Bessette-Kennedy was played by Sarah Pidgeon


Studio portrait of American lawyer and magazine publisher John F Kennedy Jr (1960 - 1999), New York, New York, 1988© Getty Images
Ahad Sanwari
Ahad SanwariSenior Writer - New York
March 12, 2026
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The Kennedy family may not be a fan of Ryan Murphy's latest controversial release, the first in his Love Story anthology series, but the viewers certainly are.

The new release, centering around the titular relationship between John F. Kennedy Jr. and his future wife Carolyn Bessette, has become a juggernaut on social media and on streaming services, and has received positive critical notices as well.

While Paul Anthony Kelly and Sarah Pidgeon have certainly won themselves fans, not every star has earned plaudits for their portrayals — case in point, Dree Hemingway's turn as Daryl Hannah, which was criticized by the actress herself (although less so for Dree and more so for the writing).

The Splash star hasn't held back when it comes to critiquing the show for its portrayal of her relationship with JFK Jr., affectionately known then as "John-John." But so far, Daryl is also the only one of JFK Jr.'s partners outside of Carolyn that has even been shown in the series.

Prior to his marriage, the entrepreneur and Kennedy scion had several other notable romances. Take a walk down memory lane with HELLO! as we revisit his dating history over the years…

Oct 11, 1981; Providence, RI, USA; JOHN F. KENNEDY JR. & girlfriend SALLY MUNRO during their College years @ Brown University in Rhode Island.© Alamy Stock Photo

Sally Munro

While attending Brown University, John met Sally Munro. They quickly became friends and eventually entered a relationship that lasted six years, ending soon after they took a trip to India in 1983. Per a close friend of his, Robert Littell, she was one of the few people not enamored by his celebrity.

In his 2005 memoir The Men We Became: My Friendship with John F. Kennedy, Jr., Robert wrote: "Her grounded sensibility was just what he needed during his first years as an adult. As for why they broke up, it seemed to me that they just reached an impasse. There was nothing more to learn from each other."

View of American couple, lawyer and publisher John F Kennedy Jr (1960 - 1999) and Christina Haag at an unspecified event, New York, New York, 1986.© Getty Images

Christina Haag

Actress Christina Haag and John had known each other since they were teenagers through mutual friends, and even went to Brown together. They became close due to their shared love for theater, but didn't start dating until after he'd broken up with Sally.

They were together for five years, with Christina also developing a close relationship with his mother Jackie Kennedy. It ended around the same time his relationship with Daryl began, with Christina immortalizing their romance in her memoir Coming to the Edge.

Brooke Shields attends the AMC Networks 2025 upfront at Spring Studios on April 09, 2025 in New York City© Getty Images

Brooke Shields

John very briefly dated Brooke Shields, with the actress recalling on The Howard Stern Show in 2023 that they went on one date and he was "the best kiss I've ever had in my life," but she didn't want to take it further because she was scared he'd blow her off. Sure enough, she claimed that the next time they saw each other while skiing, he ignored her. "He showed his true colors in that."

John F. Kennedy Jr. strains to hear a question during a press conference in New York to announce the launch of the new political magazine called "George" 07 September.  Kennedy will be the Editor-In-Chief of the non-partisan magazine which will spotlight the personalities that shape public issues. Fashion model Cindy Crawford poses as George Washington on the cover of the magazine.              © Getty Images

Cindy Crawford

In the early 1990s, John was linked with supermodel Cindy Crawford as well. However, that affair rumor seems to be unsubstantiated, as their greatest connection happened to be a professional one. Cindy was on the inaugural 1995 cover of George, a political magazine JFK Jr. launched, dressed as none other than George Washington.

sarah jessica parker glamorous hair with curls and waves© GC Images

Sarah Jessica Parker

Sarah Jessica Parker and John met in 1991 while she was on Broadway, and their highly-publicized romance lasted for six months, which the actress later dubbed the "Kennedy fiasco." She told the New York Times the year after: "I never had any idea what real fame was until I met John."

"He's a nice man, but for God's sake, I feel like I should apologize for dating him," she continued. "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.'"

John F. Kennedy, Jr. and Daryl Hannah arrive at the wedding of his cousin Edward Kennedy, Jr. in Rhode Island.© Getty Images

Daryl Hannah

JFK Jr. and Daryl had met while vacationing together in Saint Martin, but reconnected at Lee Radziwill's wedding in 1988 and started dating. As Love Story showed, their romance lasted for just over five years, but it was complicated by an overlap with another one of Daryl's partners, musician Jackson Brown.

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