EXCLUSIVE: I Was JFK Jr.'s Mistress and This is How His Love of Painting Turned into Sex Sessions
Sybil Hill began a long and steamy romance with JFK Jr. in 1991.
Feb. 18 2026, Published 6:30 p.m. ET
John F. Kennedy Jr.'s former mistress has spilled intimate details about their affair, opening up how their fling started before and continued after his doomed marriage to Carolyn Bessette, RadarOnline.com can reveal.
Sybil Hill described how the political scion's love of painting turned into steamy romps in the sack and that she developed deep feelings for JFK Jr., even exchanging love letters.
The Beginning of Their Long Affair
JFK Jr. and Sybil Hill's passionate romance began in 1991 and temporarily stopped when he married Carolyn Bessette.
Hill met JFK Jr. in January 1991, and their romance continued all the way until he and Bessette died when the small plane he was piloting crashed off the coast of Martha's Vineyard in July 1999.
The duo initially locked eyes at a Manhattan diner, where Hill noticed a "gorgeous-looking man wearing a baseball cap pointed out a vacant table," who she thought was a dead ringer for JFK Jr., only it turned out to be the real deal.
Ditching her date who had excused himself, Hill went up and introduced herself to JFK Jr., and the chemistry led to wild bedroom sessions in the years to come.
'Our Painting Sessions Often Turned Into S-- Sessions'
JFK Jr. was hot and heavy with Hill while he was still dating Bessette.
"John liked to paint, and our painting sessions often turned into s-- sessions," Hill described a bout how the artistic hobby led to fun in the bedroom.
Their passion turned to true emotion, and Hill fell hard for JFK Jr. She later discovered he kept her love notes she wrote him next to his bed.
She recalled one letter where "I just poured my heart out."
"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 and said she’d FedEx them to him. When I went into his apartment, my love letter was next to his bed," Hill revealed.
'He Was Leaving Me for Carolyn'
JFK Jr. broke things off with Hill when he decided he was going to propose to Bessette.
JFK Jr. was dating Bessette while he was seeing Hill, who was brokenhearted when she learned the former prosecutor was considering proposing to the fashion publicist.
Hill said JFK Jr. came over to her place before the engagement news broke.
"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," she revealed.
Heartbroken, Hill left Manhattan and moved to Aspen, Colorado.
However, during his rocky marriage to Bessette, JFK Jr. reached out to Hill in February 1998 to let her know he would be in Aspen for a bachelor party and pleaded with her to see him.
Sybil Hill's Final Romp With Married JFK Jr.
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JFK Jr.'s short marriage to Bessette was already on the rocks when they died in a plane crash.
On February 7, 1998, JFK Jr. called Hill to tell her he was "sneaking out of the party early,” and she picked him up in an alley next to the club, and the pair went on to have a night of passion.
"I lit a fire in the fireplace. We started out on the couch, then moved down to an Oriental rug on the floor, and ended up upstairs in the bedroom,” she remembered. "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," Hill noted.
"He told me about his problems with Carolyn and said they’d been seeing a marriage counselor. He said that he was considering a divorce, but still wanted to save the marriage. But then 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," Hill recalled saying to JFK Jr.
After their night of lovemaking together, she drove him back to his rental car outside the Caribou Club.
"As he got in the car, he gave me the peace sign. It was the last time I saw him," Hill shared.
Following the plane crash that killed JFK Jr. and Bessette a year later, Hill revealed, "I was heartbroken. I’ll never know if John would have come back to me, but I treasure the thought that he would have."
