NEWSMadonna's Bedroom Bombshell: Singer Reveals the Best S-- of Her Life Was With John F. Kennedy Jr.
Madonna and John F. Kennedy Jr. were intimate as they engaged in a fling before his death.
May 28 2026, Published 5:04 p.m. ET
Madonna just dropped a major bombshell about her favorite bed partner.
According to an outlet, in a video promoting her new album, “Confessions II,” the pop star, 67, spilled who gave her the best-ever s--.
Madonna gushed over s-- with JFK Jr.
Designer Raul Lopez asked, “Who was your best d--- down?”
Madonna insisted she was “only going to name dead people” before putting a hand over her mouth and whispering, “John Kennedy Jr.”
Lopez and the rest of the group in the room — Jeremy O. Harris, Bob The Drag Queen, Ivy Mugler and Marcello Gutierrez — gasped in shock.
“Everyone says his d--- was crazy and he was a good f---…you’re the third person I’ve heard say that,” Lopez said, to which Madonna cheekily confirmed, “Mmm hmm.”
When Were Madonna and JFK Jr. Romantically Involved?
Madonna and JFK Jr. had a fling after her split from Sean Penn.
The singer and businessman had a brief fling in the late 1980s after she split from then-husband Sean Penn.
In the 2024 book, JFK Jr.: An Intimate Oral Biography, by Liz McNeil and RoseMarie Terenzio, a friend claimed “she came on to him and it was flattery."
A pal also alleged in the biography: "Madonna was totally a fling. Nothing more. Barely a fling at that."
Christopher Andersen, who wrote books on both JFK Jr. and Madonna, said the former attorney was “dazzled by the notion of dating Madonna, the most glamorous, celebrated and, by all accounts, exciting woman of her generations.”
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JFK Jr. Wanted Madonna to Be His Cover Model
Madonna and JFK Jr.'s connection was reportedly nothing more than just a 'fling.'
Years after they sparked romance rumors, Kennedy requested Madonna pose on the cover of his magazine, George.
“John had this idea of having Madonna pose on the cover as his mom,” Terenzio explained. “We would dress her in a suit, her signature sunglasses. And a pillbox hat sitting on a stack of books.”
However, the “Vogue” artist shot down the idea and wrote him a fax that reportedly read, “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. When you want me to portray Eva Braun [Adolf Hitler’s wife] or Pamela Harriman I might say yes! Hope you’re well. Love, Madonna.”
Inside Details on Madonna and JFK Jr.'s 'Flirtation'
Madonna did not want to pose on the cover of JFK Jr.'s magazine.
In July 2016, a friend of JFK Jr. — who passed away at age 38 in 1999 — gave more intimate details on the pair’s romance.
“It was a flirtation, and when other people referred to her as M around that time, just by her first initial, he would say, ‘I started that,’” the source shared. “He called her M when he wrote or faxed her. There were no cell phones then and he was always very territorial that he started that moniker for her.”
