Madonna Says JFK Jr. Gave Her the Best Sex of Her Life

Madonna's sex confession about JFK Jr. came with a tidy loophole: she said she was “only” going to name dead people before identifying John F. Kennedy Jr. as the person who gave her the best sex of her life. It is one way to keep a panel game legally, if not emotionally, uncomplicated.

The “Like a Virgin” singer made the comment during a Confessions episode with Grindr uploaded May 29. Asked about her past relationships, Madonna paused before answering.

“Oh, my God,” she said. “I’m gonna only name dead people. Um, John Kennedy Jr.”

What Madonna said about John F. Kennedy Jr.

Madonna, whose past high-profile relationships have included Michael Jackson, Warren Beatty and Sean Penn, was linked to John F. Kennedy Jr. in the late 1980s.

When another panelist noted that Kennedy has long had a reputation as a “good f--k,” Madonna replied, “So you know it’s true.”

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Kennedy, the son of former president John F. Kennedy, died in a plane crash in 1999 alongside his wife, Carolyn Bessette Kennedy, and her sister, Lauren Bessette. That was her caveat before answering, and the reason the room could laugh without waiting for a publicist to sprint in.

Madonna also revealed her sex playlist preference

The conversation did not stop at naming names. Madonna also said she likes classical music during sex, singling out Japanese composer Ryuichi Sakamoto.

“Ryuichi Sakamoto or stuff like that,” she said. “It’s like building tension but it’s also romantic. It rises and falls. It builds up and it builds up and then there’s a drop.”

For an artist who has spent decades turning desire into performance, that answer is not exactly shocking. It is, however, very specific, which is often where the better celebrity confessions live.

Sarah Jessica Parker described the glare of dating JFK Jr.

Madonna is not the only celebrity whose Kennedy connection has become part of pop-culture memory. Sarah Jessica Parker dated Kennedy in the early 1990s, when he was best known publicly as a member of America’s most scrutinized political family and later became the editor of George magazine.

In a 1992 interview with The New York Times, Parker said dating him gave her a new understanding of fame.

“We would go places where there wasn't a soul around, and the next day I'd see pictures of us there in the tabloids,” she said. “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. It has become the defining factor in the person I am.”

Parker went on to marry Matthew Broderick in 1997.

Brooke Shields remembered one very memorable kiss

Brooke Shields has also spoken about a brief romantic moment with Kennedy, though hers came with a firm boundary. She said she had one date with him and chose not to have sex because she felt emotionally overwhelmed by him.

“I wouldn’t sleep with him because I kind of loved him too much,” Shields recalled. “We went back to this chalet hotel he was in. He kissed me and it was the best kiss I’d ever had in my life.”

Kennedy, though, is the thread running through all three stories: the charm, the attention and the way even a private date could end up in the public record.

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madonna sex confessionjohn f kennedy jrcelebrity relationshipsbrooke shields

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