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Madonna makes X-rated confession over romance with John F. Kennedy Jr
Home>Entertainment>Celebrity
Published 16:17 30 May 2026 GMT+1

Madonna makes X-rated confession over romance with John F. Kennedy Jr

They were briefly together, but she still remembers him

Joe Harker

Joe Harker

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Madonna has revealed that of all her exes, the ones who are no longer alive at least, her favourite was John F. Kennedy Jr, the son of the late US President of the same name.

According to Page Six, Madonna has been promoting her new album Confessions II by chatting with dating app Grindr with a video where she was asked a lot of personal questions.

During the Q&A with Madonna, fashion designer Raul Lopez asked her: "What was your best f**k? Who was your best d**k-down?"

As you do, and Madonna did answer the question with the caveat that she wouldn't be including any partners past or present in the conversation who were still in the land of the living.

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She said: "I’m only going to name dead people. John Kennedy Jr."

Madonna was asked which former lover she liked the best, of those no longer with us she said John F. Kennedy Jr (Michael Brennan/Getty Images)
Madonna was asked which former lover she liked the best, of those no longer with us she said John F. Kennedy Jr (Michael Brennan/Getty Images)

They had a brief fling in the late 80s after Madonna had separated from her husband Sean Penn, and the group of people the singer was talking to said they'd heard before that Kennedy had been what we shall politely term a proficient lover.

A couple of years ago a book titled JFK Jr.: An Intimate Oral Biography said the relationship between the president's son and Madonna was 'nothing more' than a fling

"She came on to him, and it was flattery. She was at the top of her game,” the book's authors wrote.

"He loved her body. It was all about physical attraction; it wasn’t going to be anything beyond that."

One person who wasn't a fan of the fling was former First Lady Jackie Kennedy, as according to People she didn't like that Madonna was still married to Penn while it was happening.

JFK Jr had a brief fling with Madonna in the 80s (Bettman/Getty)
JFK Jr had a brief fling with Madonna in the 80s (Bettman/Getty)

Kennedy’s executive assistant RoseMarie Terenzio claimed that the former couple stayed in touch enough that in 1996, Kennedy asked Madonna to pose as his mother for the cover of his own political magazine.

Someone would have a field day with that one.

"We’ll have her in the pillbox hat, sitting on a stack of books. If it doesn’t bother me, why should it bother anyone else?" he'd said at the time according to his assistant.

Madonna didn't seem to be much of a fan of the idea, however, as she responded with a fax message (remember, it was the 90s) to decline the offer to pose on the front of her former lover's mother on his magazine cover.

Kennedy shared some of the bad luck certain members of his family have experienced, as he died in a plane crash in 1999.

Featured Image Credit: Dia Dipasupil/Getty Images

Topics: Madonna, Celebrity

Joe Harker
Joe Harker

Joe graduated from the University of Salford with a degree in Journalism and worked for Reach before joining the LADbible Group. When not writing he enjoys the nerdier things in life like painting wargaming miniatures and chatting with other nerds on the internet. He's also spent a few years coaching fencing. Contact him via [email protected]

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@MrJoeHarker

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