Meet JFK Jr.’s Ex-Mistress, Sybil Hill, Amid Steamy New Details About Their Affair And Love Letters

John F. Kennedy Jr.’s love story with his wife, Carolyn Bessette Kennedy, and his long rumoured affairs with multiple women have regained attention with the release of Ryan Murphy’s FX miniseries Love Story: John F. Kennedy Jr. and Carolyn Bessette, whose first episode aired on February 12, 2026. With every new episode diving into yet another profound chapter of the late couple’s tragic marriage, some of Kennedy’s old friends and close ones have come up with new revelations about his tumultuous love life. Among them is a woman who loved the late Camelot prince with all her heart: Sybil Hill.

Long before tragedy struck off the coast of Martha’s Vineyard in 1999, John F. Kennedy was living a life that often blurred the lines between his public image and his deep personal desires. Nearly 26 years after Kennedy and Bessette’s tragic death, Sybil Hill is revisiting her alleged long-running affair with the political royalty.

The romantic affair between JFK Jr. and Sybil Hill has long been a matter of public debate, and it’s one of the many myths and mysteries surrounding America’s so-called Camelot scion. Now 60, Hill has never truly forgotten the love and passion she once allegedly shared with Kennedy.

When did the affair between JFK Jr. and Sybil Hill start?

John F. Kennedy was popularly labelled the “World’s Most Eligible Bachelor”, and every woman from the elite circle wanted to be a part of his story. His romantic escapades have been quite popularly discussed, with former friends often mentioning how the late American attorney openly wondered if he was a s-x addict. Despite his many romantic entanglements, Sybil Hill was reportedly the one woman he continually returned to, even as he struggled with the guilt of straying from his deeply held Catholic values.

In a new interview with RadarOnline.com, the painter opened up about her love affair with Kennedy, spilling some rather steamy details about their carnal interactions. According to Hill, she and Kennedy first met in January 1991 at a Manhattan dinner, and it was a spontaneous introduction. And before they knew it, their interaction evolved into what she described as an on-and-off relationship that allegedly lasted until Kennedy’s death in July 1999. 

JFK Jr.’s love of painting was what allegedly set the stage for their connection. Hill, a painter by profession, revealed that she and Kennedy often met for artistic endeavours, but those painting sessions often turned intimate. “John liked to paint, and our painting sessions often turned into s– sessions,” she told the publication. With repeated meet-ups and intimate romps, their bond deepened over time, both physically and emotionally.

Hill and Kennedy’s on-and-off relationship over the years

Hill and Kennedy allegedly had a tradition of sharing handwritten love notes whenever they met. It was much later when Hill realised that Kennedy had kept every single love note she had written for him. The 60-year-old painter recalled the time she went to Kennedy’s apartment and discovered a deeply personal love letter on his bedside. This letter was allegedly the one where she had “poured my (her) heart out” and declared her love. In Hill’s words:

“Once he asked me to go to his apartment and pick up some maps that he needed for an expedition overseas. He wanted me to take the maps to his mother… When I went into his apartment, my love letter was next to his bed.”

Unlike his other romantic entanglements, Kennedy’s connection with Hill was said to run deeper than a fleeting affair. He allegedly continued returning to her even after he began dating Carolyn Bessette, the woman he publicly described as the love of his life. 

JFK Jr. left Sybil Hill for Carolyn Bessette

The affair gradually ended when Kennedy committed himself to Carolyn and started feeling conflicted about his mistress. Hill says the relationship fractured when Kennedy grew serious about Bessette, whom he secretly married in 1996. She recalled a final emotional encounter before news of Kennedy’s engagement became public, claiming she had realised he had chosen Carolyn. She claims to remember the date of their final meeting, February 7, 1998.

That night, Kennedy allegedly snuck out of a party and met Hill at her house. Sharing steamy details from their passionate moments, the painter recalled seeing the guilt on Kennedy’s face and realising that their relationship had neared its end. She told the publication:

“I lit a fire in the fireplace… I teased him, ‘Are you like a sailor with a girl in every port?’ John gazed into my eyes and said, ‘No, Sybil, you’re the only one.’ But he obviously felt guilty… We made love, but I could see he was conflicted. Finally, I put my hand over John’s heart and said, ‘You have to follow your heart.’ He dropped his head and said simply, ‘I’m sorry.’ I knew he was leaving me for Carolyn.”

Did JFK Jr. return to Sybil Hill after marrying Carolyn Bessette?

According to Hill’s recent revelations, yes, he did. In 1998, when he was undergoing a rough patch in his marriage to Carolyn Bessette, Kennedy allegedly reconnected with his former mistress for one last time. Their final interaction happened in Aspen, Colorado, and it left her with lingering questions about what their future might have been. Despite trying to make the marriage work, John and Carolyn had started to realise that they were probably headed for a divorce.

Recalling her final meeting with Kennedy, Hill shared how the latter shared his ongoing marital problems and that he and Carolyn had been seeing a marriage counselor. He was desperate to save the marriage, but was also considering a divorce. Based on what Hill said, John was planning to see where the marriage was headed in the next two years, and if it didn’t work, he wanted to return to Hill. In her words:

“He startled me by asking, ‘What do you think you’ll be doing in two years?’ I took it to mean that he might be free in two years and was asking if I’d still be available. I told him, ‘I’ve never stopped loving you, and I’ll love you forever.”

It’s no news that JFK Jr. and Carolyn Bessett had a strained marriage, with things going south within a year of their marriage. Ahead of that fatal plane crash, the marriage was on the verge of breaking up, and things were not getting any better. That Colorado meeting was allegedly the last time that Sybil Hill saw JFK Jr. in person. Months later, on July 16, 1999, Kennedy and Bessette died in a plane crash, along with the latter’s sister, Lauren Bessette. And Hill was forever left with a question that would never be answered.

Who is Sybil Hill?

Beyond her infamous affair with JFK Jr., Sybil Hill made a name for herself with her artwork. Now married as Sybil Hill Carter, she is a renowned painter based in Colorado. According to her official website, the subject matter of her paintings often centres on horses and American flags, which she blends with vintage materials, poetry, and abstract influences. A celebrated artist in the country, Hill reportedly sold hundreds of pieces to collectors across the U.S. and overseas in the past decade. Today, she paints while raising her family in the Colorado mountains and is known to frequently donate her work to charitable causes.

Whether Sybil Hill’s new revelation becomes another debated chapter in his marriage or becomes another example of tragic romance, it’s clear someone else once loved him, and perhaps still wonders what might have been if John lived.

Also Read: JFK Jr. Had A Love Child? Friend Says He ‘Accidentally’ Fathered A Baby Over Troubles With Carolyn