Madonna has revealed that the late John F. Kennedy Jr. was the best sexual partner of her life — but only among her deceased exes. The 67-year-old singer made the confession during a video for the LGBTQ+ dating app Grindr, where fashion designer Raul Lopez asked her: "What was your best f***? Who was your best d***-down?"
Madonna's Candid Revelation
Madonna responded by drawing a line: "I'm going to only name dead people." She then whispered, "John Kennedy Junior," prompting gasps of excitement from fellow panelists. Lopez added, "Everyone said his d*** was crazy and he was a good f***. You're the third person to say that." Madonna confirmed with a simple "Mm-hmm."
The singer was romantically linked to JFK Jr. in the late 1980s, shortly after her separation from first husband Sean Penn. According to the 2024 book JFK Jr.: An Intimate Oral Biography by RoseMarie Terenzio and Liz McNeil, the relationship was nothing more than a fling. "She came on to him, and it was flattery. She was at the top of her game. He loved her body. It was all about physical attraction; it wasn't going to be anything beyond that," the authors wrote.
Jackie Kennedy's Disapproval
JFK Jr.'s mother, Jacqueline Kennedy Onassis, was reportedly not a fan of the romance. According to J. Randy Taraborrelli's 2023 biography Jackie: Public, Private, Secret, Jackie's issue with Madonna was that she was still legally married to Penn until 1989. Taraborrelli told People magazine: "[Jackie's] problem with [Madonna] was that she was married. She 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."
JFK Jr.'s Magazine Offer
Despite their split, JFK Jr. once asked Madonna to pose as his mother on the cover of his political lifestyle magazine, George, in 1996. "Wouldn't that be a riot?" he 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?" However, Madonna later faxed a decline.
Madonna, who is promoting her upcoming album Confessions II, has been romantically linked to many famous figures, including Jean-Michel Basquiat, Tupac Shakur, and Warren Beatty. She was married to filmmaker Guy Ritchie from 2000 to 2008.
