Madonna says John F. Kennedy Jr. was the best sex of her life — with a caveat

Stiff competition!

Asked recently to name her best-ever lay, Madonna said she was prepared only to rank the dead ones. But of all her extinct exes, she picked John F. Kennedy Jr.

The Material Girl is promoting her new album, “Confessions II,” by working with Grindr. And instead of doing the usual press tour, she made a video with playwright Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez and ID’s Marcello Gutierrez, who was asking the questions.

Madonna and JFK Jr.
Madonna said in a video for Grindr that the best sex of her life was with John F. Kennedy Jr. (She is seen above with him at an event in Las Vegas in 1997.)GTRES / Shutterstock
Madonna and Sean Penn walking down a street, wearing sunglasses at night, smiling
She was married to Sean Penn (shown here in New York in 1986) during her fling with Kennedy.Getty Images

“I’m only going to name dead people,” says the “Papa Don’t Preach” superstar, before covering her mouth and whispering, “John Kennedy Jr.” — inciting a choral “Shut upppppppp!” from the group so loud that the late scion may well have heard it.

Raul Lopez in a black-and-yellow outfit
Raul Lopez (seen above at the Fashion Scholarship Fund annual gala in March) asked whom she had the best sex with.Getty Images for Fashion Scholarship Fund

Lending valuable journalistic context, Lopez adds, “Everyone says his d–k was crazy and he was a good f–k.”

“Mmm hmm,” Madonna confirms, with a inescapable degree of satisfaction.

“You’re the third person I’ve heard say that,” Lopez, who should perhaps be considered as Anderson Cooper’s replacement on “60 Minutes,” said.

The pair dated very briefly in the late 1980s.

Christina Haag and JFK Jr., both dressed formally, sitting down at a table
JFK Jr .was dating model Christina Haag when he and Madonna met.Getty Images
Jeremy O. Harris, dressed in a tuxedo, standing up
“Slave Play” writer Jeremy O. Harris was among the group quizzing Madonna in the video.Getty Images for Vanity Fair

“Madonna was totally a fling,” one of Kennedy’s close pals said in “JFK Jr.: An Intimate Oral Biography” by RoseMarie Terenzio and Liz McNeil, which came out in 2024. “Nothing more. Barely a fling at that.”

The book claims they met while he was dating actress Christina Haag and Madonna was married to Sean Penn.

The unnamed Kennedy friend says that the pop icon came on to JFK Jr., “and it was flattery — she was at the top of her game.”

It was “all about physical attraction, it wasn’t going to be anything beyond that,” the source claimed.

John F Kennedy Jr. and  Carolyn Bessette,  walking down a street, talking to and looking at each other
Needless to say, Kennedy went on to marry Carolyn Bessette (seen together above heading to Bubby’s in 1997).Lawrence Schwartzwald

Rather impressively — if the book is to be believed — John-John won Madonna’s boudoir blue ribbon (deceased category) without all the, er, usual tools at his disposal.

“They didn’t have the protection measures and she was very on top of HIV prevention,” the pal explains.

That didn’t stop the couple from having “fun in other ways” and Kennedy remarking that the “Vogue” singer had “one of the most beautiful bodies he had ever seen.”

According to the book, many years later, Penn appeared on the December 1998 cover of Kennedy’s George magazine, and the two had dinner.

The friend says that JFK Jr. assured Penn that “he never knew Madonna in the biblical sense.”

Madonna and Akeem Morris, wearing black, at the Met Gala red carpet
Madonna is currently dating Akeem Morris. They attended the Met Gala together earlier this month.Kevin Mazur/Getty Images for The Met Museum/Vogue

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And, proving that he was from a family of lawyers, that may very technically have been true.

Kennedy’s competition amongst late lovers include Jean-Michel Basquiat, Luke Perry and Tupac Shakur.

We’re told the video will be available on Grindr’s in-app media hub “Grindr Presents” and on its YouTube and Instagram accounts.

The app company is also putting out limited-editon, picture-disc vinyl copies of the new record.

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