Madonna has spoken out about her brief romance with the late John F. Kennedy Jr., calling him her best sexual partner — but only on one condition.
The 67-year-old singer was romantically linked to the son of former President John F. Kennedy and First Lady Jacqueline Kennedy in the late Eighties. Shortly before her relationship with Kennedy — who died in 1999 when the aircraft he was piloting crashed — Madonna had separated from her ex-husband, Sean Penn.
In a new video for the LGBTQ+ dating app Grindr, fashion designer Raul Lopez asked the “Material Girl” singer: “What was your best f***? Who was your best d***-down?”
“I’m going to only name dead people,” Madonna said, drawing a line. She then whispered: “John Kennedy Junior.”
The fellow panelists in the interview were shocked by Madonna’s answer and gasped in excitement. “Everyone said his d*** was crazy and he was a good f***,” Lopez said about Kennedy. “You’re the third person to say that.”
Madonna, who’s promoting her upcoming album Confessions II, confirmed Lopez’s statement by responding, “Mm-hmm.”
According to the 2024 book JFK Jr.: An Intimate Oral Biography — written by Kennedy’s executive assistant RoseMarie Terenzio and People editor-at-large Liz McNeil — the attorney had “nothing more” than a fling with Madonna.
“She came on to him, and it was flattery. She was at the top of her game,” Terenzio and McNeil wrote. “He loved her body. It was all about physical attraction; it wasn’t going to be anything beyond that.”
However, Kennedy’s mother allegedly wasn’t a fan of the romance, according to J. Randy Taraborrelli, who wrote the 2023 autobiography Jackie: Public, Private, Secret.
“[Jackie’s] problem with [Madonna] was that she was married,” Taraborrelli told People in 2023, referring to how Madonna was still legally married to Penn until 1989. “[Jackie was also] confounded by Madonna’s penchant for attention. Jackie had spent her entire celebrity life avoiding paparazzi, whereas Madonna would court paparazzi. And Jackie just couldn’t understand any of that.”
Despite their split, Kennedy asked the “Vogue” singer to pose as his mother on the cover of his political lifestyle magazine, George, in 1996.
“Wouldn’t that be a riot?” Kennedy asked, according to Terenzio’s 2012 memoir, Fairy Tale Interrupted.
“‘We’ll have her in the pillbox hat, sitting on a stack of books. … If it doesn’t bother me, why should it bother anyone else?’” Terenzio wrote, recalling Kennedy’s remarks. However, the book said that Madonna later sent a fax to decline the request.
Aside from Kennedy, Madonna has been romantically linked to many famous faces, including Jean-Michel Basquiat, Tupac Shakur and Warren Beatty. She was married to filmmaker Guy Ritchie from 2000 to 2008.
