Madonna Reveals John F. Kennedy Jr. Was Her Best Lover, Agrees He Was ‘Crazy’ In Bed

Nobody dishes on their personal life quite like Madonna.

The “Vogue” singer, 67, is skipping the traditional press tour for her new album, Confessions II, by teaming up with Grindr for a candid video instead. During the chat, previewed by Page Six on Wednesday, May 28, she was joined by playwright Jeremy O. Harris, Bob the Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and ID’s Marcello Gutierrez.

Madonna didn’t hesitate when Lopez asked her about her best lover. “I’m only going to name dead people,” she said, before leaning in and whispering, “John Kennedy Jr.”

Lopez didn’t mince words, adding, “Everyone says his d**k was crazy and he was a good f**k.”

Madonna — who dated the late George founder briefly in the 80s — responded with a knowing, “Mmm hmm.”

“You’re the third person I’ve heard say that,” Lopez added.

According to JFK Jr.: An Intimate Oral Biography by Rosemarie Terenzio and Liz McNeil, published in 2024, Madonna and JFK Jr.’s romance was never anything serious.

“Madonna was totally a fling,” a close friend of JFK Jr.’s said in the book, per Page Six in July 2024.

The book claims they crossed paths while JFK Jr. was dating actress Christina Haag and Madonna was still married to Sean Penn.

Madonna reportedly made the first move, and JFK Jr. was flattered. “She was at the top of her game,” the source said, per InStyle. The attraction, however, was purely physical. “It wasn’t going to be anything beyond that,” the friend added.

JFK Jr. had also asked the singer to channel his mother, Jacqueline Kennedy, for a cover of George, complete with a suit, sunglasses and a pillbox hat.

However, Elle reported that she passed the offer politely with a note that said, “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.”

The book also suggested the couple never slept together in the traditional sense, due largely to Madonna’s strict stance on HIV prevention.

They reportedly found “fun in other ways,” and JFK Jr. later told friends that the Queen of Pop had “one of the most beautiful bodies he had ever seen.”