From Brooke Shields to Carolyn Bessette: Inside John F. Kennedy Jr.’s dating history

During his senior year of high school at Phillips Academy, JFK Jr. developed strong feelings for his classmate Jenny Christian – a relationship that left a lasting impression on him. 

His close friend Sasha Chermayeff would later describe Jenny as “the first love of his life, no doubt.”

Sasha recalled that John was especially drawn to Jenny’s intellect and sense of humour. “He really admired her,” she said in An Intimate Oral Biography – RoseMarie Terenzio and Liz McNeil’s biography on JFK Jr.

While attending Brown University, John began a relationship with fellow student Sally Munro.

According to his friend and Brown classmate Chris Oberbeck, who first introduced the two, Sally stood out right away. “She was a New England girl – attractive, smart, and from a big family,” Chris recalled. “She wasn’t trying to be like everyone else.”

Actress and model Brooke Shields had a brief romantic encounter with JFK Jr. in the early 1980s. 

Brooke revealed in multiple interviews – and her biography – that they went on a single “real” ski date in Aspen, during which she experienced what she called the “best kiss” of her life. 

Despite her strong feelings – she said she had been “madly in love” with him since childhood – Brooke ultimately declined to pursue a physical relationship, fearing emotional vulnerability. 

She described JFK Jr. as a “delicious kisser” with “full, beautiful” lips, though she emphasised that they never officially dated. 

After graduating college, John began a relationship with another Brown classmate, Christina Haag. The two shared a love of theatre and quickly formed an intense bond.

Although they had lived in the same group house at Brown, they had both been involved with other people at the time. That changed after graduation, when Christina ended a long-term relationship. 

According to John’s close friend Robbie Littell, the news sparked an enthusiastic reaction. “John ran to the window and yelled out, ‘She’s free – the girl I’m going to marry!’,” Robbie recalled in An Intimate Oral Biography.

John and Christina soon began dating while appearing in a play together, and their relationship lasted for five years. Christina later reflected on their time together in her 2011 memoir, Come to the Edge.

After his relationship with Christina Haag ended, JFK Jr. went on to date actress Daryl Hannah. 

Amelia Barlow – one of the three daughters of John’s close friend, Grateful Dead lyricist John Perry Barlow – remembered Hannah fondly. Reflecting on their relationship in An Intimate Oral Biography, she said it had an almost magical quality.

“I can only tell you what their relationship felt like to me – it felt fantastical, adventurous,” Amelia recalled. “It felt somewhat young and maybe a little naïve or immature compared to his relationship with Carolyn. There was a bit more fire – and more fighting.”

In the late 1980s, John briefly had a fling with pop superstar Madonna. According to a friend quoted in An Intimate Oral Biography, the connection began when the singer showed interest in him. “She came on to him, and it was flattering,” the friend recalled.

At the time, Madonna was still married to actor Sean Penn, though their relationship was nearing its end. John and Madonna remained friendly over the years, and later he reached out with an unexpected request when he was launching his political magazine, George.

According to RoseMarie Terenzio, John once asked Madonna to appear on the magazine’s cover styled as his mother, Jacqueline Kennedy Onassis. “John had this idea of having Madonna pose on the cover as his mom,” she said. “We would dress her in a suit, her signature sunglasses, and a pillbox hat, sitting on a stack of books.”

Madonna ultimately declined – responding playfully. “Dear Johnny boy,” she wrote in part, “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.”

John met model Julie Baker in 1989, though she initially had no idea he was interested in her.

“I had no idea he even liked me or noticed me,” Julie recalled to the authors of An Intimate Oral Biography. “And less than a week later, he called me. I was actually surprised to hear from him.”

His first invitation didn’t exactly win her over. John asked if she wanted to join him at a poetry reading – an idea Julie quickly turned down. “To me that sounded so boring,” she said, laughing. “It didn’t matter that it was John.”

A few days later, he tried again, this time inviting her to see comedian Andrew Dice Clay perform. The second plan was a success. “We went and we had a blast,” Julie said.

The two dated for a time but ultimately remained close friends. In fact, Julie said they continued meeting for regular lunches, right up until the final week of John’s life.

It was Carolyn Bessette-Kennedy – whom John met in the early 1990s – who would ultimately capture his heart. After a whirlwind courtship, the couple married in a private and intimate ceremony in 1996.

When they first met, both were seeing other people, but according to John’s friend Sasha, his feelings were immediate. “He was obsessed from the minute he met her,” she recalled. Carolyn, however, didn’t immediately fall under his spell.

Friend Jack Merrill remembered the first time he was supposed to meet her. “John had been telling me about Carolyn,” he said. “He was like, ‘This is my new girlfriend and I really like her and she’s gonna come by.’ And then the chair is empty.” When she didn’t arrive on time, John was both embarrassed and irritated. 

Jack, however, found the moment amusing. “I thought it was hysterical. Most girls did not do that to John.”

When Carolyn finally arrived – about an hour late – Jack said the mood instantly shifted. “She sat down next to me and we were laughing from the minute I first looked at her,” he recalled.

Their relationship remained passionate and, at times, turbulent throughout their marriage. It continued that way until their final day together on July 16, 1999, when they boarded a small plane John was piloting en route to Martha’s Vineyard.

Despite the challenges they faced, those close to them said neither wanted to walk away. As RoseMarie Terenzio put it, their goal was always to repair what wasn’t working rather than end the relationship.