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 asking the questions.
Page Six got hold of the video before its release, and in one especially memorable moment, Lopez asks, “Who was your best d**k down?”
“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.
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.
“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 she was married to Sean Penn.
The unnamed Kennedy friend says that Madonna 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.
Rather impressively — if the book is to be believed — Jon Jon 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.”
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. Stiff competition!
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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