Madonna has said John F. Kennedy Jr. was the best partner she’s had in bed — though she added a key condition.
The “Vogue” singer made the claim while discussing her sex life as she promotes her upcoming album, Confessions II.
As part of a collaboration with Grindr, Madonna joined a conversation featuring several celebrity guests, including designer Raul Lopez and dancer Ivy Mugler, who posed candid questions ahead of the release.
During the chat, one question cut straight to the point: “Who was your best d*** down?” But Madonna said there was a rule to what she was willing to reveal.
“I’m only going to name dead people,” the 67-year-old said, before naming John F. Kennedy Jr., the son of the 35th US president.
Kennedy Jr. died in 1999 at age 38, when the small plane he was flying crashed into the Atlantic Ocean.
Lopez replied: “Everyone says his d*** was crazy and he was a good f***.
“You’re the third person I’ve heard say that!”
“Mmm hmm,” Madonna confirmed.
The two were linked briefly in the late 1980s. Reports from the time suggested Kennedy Jr. was “totally in awe” of Madonna, who was then one of the most famous people on the planet.
At that point, he was working in Manhattan as an assistant district attorney.
Christopher Anderson, author of The Day John Died, described Kennedy Jr.’s reaction to dating the superstar in his biography: “For his part, John, who was not above being star struck, was dazzled by the notion of dating Madonna.
“The most glamorous, celebrated, and, by all accounts, exciting woman of her generation.”
Anderson also wrote that the spark was obvious from the start, saying you could “see it in his eyes that first time they met.”
Even so, the relationship was short-lived, and both later moved on.
In the same biography, one of Kennedy Jr.’s friends reportedly downplayed the romance, saying “Madonna was totally a fling.”
“It was all about physical attraction, it wasn’t going to be anything beyond that,” they added.
There was also an awkward complication at the time: Madonna was technically still married to I Am Sam actor Sean Penn, and the situation allegedly didn’t go over well with Jacqueline Kennedy Onassis, Kennedy Jr.’s mother.
Kennedy Jr. later married Carolyn Bessette-Kennedy in 1996. Madonna went on to marry Guy Ritchie in 2000; the pair divorced in 2008.
Madonna is now dating 29-year-old soccer player Akeem Morris, after the two made their relationship public in mid-2024.