In a very sensual admission, Madonna said that she had the finest sex of her life with the late John F. Kennedy Junior.
The 67-year-old Vogue singer is said to have had an affair with John Jr. in 1988, and romance rumors about him have surrounded her all of her life.
In a recent video promoting her upcoming album, Confessions II, she collaborated with the LGBTQ+ dating app Grindr, offering an insight into the veracity of the rumors.
Fashion designer Raul Lopez asked the Queen of Pop to name the “best d*** down” she had ever had in a preview that Page Six was able to secure. Madonna responded, “I’m only going to name dead people,” before covering her lips and whispering, “John Kennedy Jr.”
“Everyone says his d* was crazy and he was a good f*,” Raul continued. Madonna responded with a “Mmmhmm.”
The 67-year-old Madonna has acknowledged that she had the finest sex of her life with the late John F. Kennedy Junior.
The Vogue singer has been the subject of romantic rumors throughout her life, allegedly having an affair with John Jr. in 1988 (both shown in 1997).
“You’re the third person I’ve heard say that,” Raul went on.
As her notoriously tumultuous marriage to Sean Penn was nearing its conclusion, Madonna began seeing John in the late 1980s.
On July 16, 1999, John lost his life when the small aircraft he was flying crashed into the Atlantic Ocean off the coast of Martha’s Vineyard, Massachusetts.
Among his rival late loves are Tupac Shakur, Luke Perry, and Jean-Michel Basquiat.
The romance was brief and never turned into anything serious, according to RoseMarie Terenzio and Liz McNeil’s 2024 book JFK Jr.: An Intimate Oral Biography. “Madonna was totally a fling.” Nothing more. In the novel, one of John’s close pals remarks, “Barely a fling at that.”
The memoir claims that when Madonna was married to Sean Penn, John was seeing actress Christina Haag.
In a recent video promoting her upcoming album, Confessions II, she collaborated with the LGBTQ+ dating app Grindr, offering an insight into the veracity of the rumors.
Madonna rejected John’s request to have her appear as his mother on the cover of the magazine he edited, joking that her “eyebrows weren’t thick enough.”
According to an oral history of the late John Jr. and the debut of George, the singer stated that she “might say yes” to playing Adolf Hitler’s wife Eva Braun but that she could not do Jackie Kennedy justice.
A wide range of celebrities and former coworkers describe how the former president’s son attempted—and occasionally failed—to attract A-listers and even royalty to collaborate with his magazine in a comprehensive article published by The Hollywood Reporter to commemorate 20 years since his untimely passing.
Rosemarie Terenzio, executive assistant, describes how Princess Diana declined an interview with John Jr., who co-founded George with Michael J. Berman in 1995, after they had tea.
Others describe how a note meant for Jack Nicholson, in which John Jr., who passed away at the age of 38, informed the actor that he was secretly getting married and begged him to stay on the cover, never made it to the celebrity.
“There were always things that we’d think he was going to be weirded out about but he wasn’t,” recalls co-founder Berman. “He wanted to do a cover about his mother.” It was his idea, something about being honest. He wanted someone sitting atop a stack of all the books ever written about his mother, dressed like her.
“It sounds great, but we don’t need the books,” I thought. He asked Madonna to do it over the phone. We thought, “Holy s**t, you’re going to see Jackie Kennedy on the cover with the hair and sunglasses, and then you’re going to look again and it’s Madonna.”
Terenzio describes how she responded in a fax, referring to him as “Johnny Boy,” but the pop sensation declined.
“He faxed Madonna a note,” she said. She also called, and I seem to recall that she left a message. Hello, this is Madonna phoning for John. “I’m not sure if this is the correct number, but this is the number that he gave me,” she said, obviously irritated that she was on voicemail. “So he told her the idea, and she faxed a note back.” Because she enjoyed having sex with him, it said, “Dear Johnny Boy,” “Thank you for asking me to be your mother, but I’m afraid I could never do her justice.” For starters, my eyebrows aren’t thick enough. I might agree to play Eva Braun if you want me to.
