Madonna has revealed that the late John F. Kennedy Jr. was her best sexual partner, but only among deceased individuals. The 67-year-old singer made the disclosure 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?”
“I’m going to only name dead people,” Madonna said, before whispering: “John Kennedy Junior.” The fellow panelists reacted with shock and excitement. Lopez commented, “Everyone said his d*** was crazy and he was a good f***. You’re the third person to say that.” Madonna confirmed this with a “Mm-hmm.”
Madonna and Kennedy had a brief romance in the late 1980s, shortly after her separation from first husband Sean Penn. According to the 2024 book JFK Jr.: An Intimate Oral Biography, the relationship was purely physical and not serious. “She came on to him, and it was flattery. She was at the top of her game,” wrote Kennedy’s executive assistant RoseMarie Terenzio and People editor-at-large Liz McNeil. “He loved her body. It was all about physical attraction; it wasn’t going to be anything beyond that.”
Kennedy’s mother, Jacqueline Kennedy Onassis, was reportedly not a fan of the romance. Biographer J. Randy Taraborrelli noted that Jackie had issues with Madonna being still legally married to Penn until 1989 and with her attention-seeking behaviour. Despite their split, Kennedy asked Madonna to pose as his mother for the cover of his magazine George in 1996, but she declined.
Madonna is currently promoting her upcoming album Confessions II. She has been linked to several other famous figures, including Jean-Michel Basquiat, Tupac Shakur, and Warren Beatty, and was married to filmmaker Guy Ritchie from 2000 to 2008.
