Madonna has revealed that John F. Kennedy Jr. was the best lover she ever had, but only among those who are no longer alive. The singer made the admission during a video Q&A with dating app Grindr, where she was asked: "What was your best f**k? Who was your best d**k-down?"
Answering with the caveat that she would only name deceased partners, Madonna said: "I’m only going to name dead people. John Kennedy Jr." The pair had a brief fling in the late 1980s after Madonna separated from her then-husband Sean Penn.
According to a 2021 book titled JFK Jr.: An Intimate Oral Biography, the relationship was "nothing more" than a fling. The book's authors wrote: "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."
Former First Lady Jackie Kennedy reportedly disapproved of the fling because Madonna was still married to Penn. Biographer J. Randy Taraborrelli claimed Jackie was "confounded by Madonna's penchant for attention" and her tendency to "court paparazzi."
Kennedy's executive assistant RoseMarie Terenzio said the former couple stayed in touch, and in 1996 Kennedy asked Madonna to pose as his mother for the cover of his political magazine. Madonna declined the offer via fax.
Kennedy Jr. died in 1999 alongside his wife Carolyn Bessette-Kennedy and sister-in-law Lauren Bessette when the plane he was piloting crashed into the Atlantic Ocean. During the same Q&A, Madonna also named Puerto Ricans, Dominicans, Brazilians, and Jamaicans as the best nationalities in bed, and added that sex is unlikely to be great "if you have a bad relationship with your mother."
