Madonna Reveals John F. Kennedy Jr. Was Her 'Best' Lover During Candid Q&A

Despite it being only a short-lived romance, Madonna recently revealed that John F. Kennedy Jr. was the "best d–k down."

While promoting her new "Confessions II" album, Madonna was joined by playwright Jeremy O. Harris, Bob the Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and ID's Marcello Gutierrez for a playful Q&A when Lopez asked her: "Who was your best d–k down?" Page Six reports.

Keeping the list to only "dead people," Madonna said, John F. Kennedy Jr., which left jaws on the floor. "Everyone says his d–k was crazy and he was a good f-k," Lopez said, adding, "You're the third person I've heard say that."

Madonna shared, "So, you know it's true."

Then Mugler wondered if "Italians do it better?" Surprisingly, Madonna gave it up for "Puerto Ricans, Dominicans, Brazilians, Jamaicans," but added that sex might not be as great "if you have a bad relationship with your mother."

Madonna also revealed her favorite post-coital meal as being "club sandwiches" or a "grilled cheese."

In the late '80s, Madonna and Kennedy had a brief romance where, apparently, "She came on to him, and it was flattery," a friend shared in An Intimate Oral Biography, via People. Perhaps most surprisingly, Kennedy later asked Madonna to pose for the cover of his political magazine, George.

"John had this idea of having Madonna pose on the cover as his mom," Terenzio said. "We would dress her in a suit, her signature sunglasses. And a pillbox hat sitting on a stack of books," RoseMarie Terenzio, one of the book's authors, said.

But posing was not in the cards, and Madonna sent him a fax, writing, "Dear Johnny boy, Thanks for asking me to be your mother, but I'm afraid I could never do her justice. My eyebrows aren't thick enough for one."

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This story was originally published May 30, 2026 at 4:08 AM.