If there is one thing that cannot be said about Madonna, it is that she is shy.
Over more than 40 years of her career, the 67-year-old Queen of Pop has dealt with almost every provocative subject imaginable, shamelessly and boldly — even when she drew fire for it, and she certainly drew plenty along the way.
But despite her almost constant engagement with explosive topics, especially those related to sex, it turns out she still maintains a little discretion, at least when it comes to her partners in bed.
This week, Madonna was asked in a new interview who was the best sex she ever had. She agreed to answer, but with a particularly morbid caveat: “I’ll only say the names of dead people,” she said, before revealing the outstanding late contender to the interviewer: John F. Kennedy Jr.
The interview, incidentally, was part of a collaboration with the gay dating app Grindr, so interviewer Raul Lopez did not bother with refinement or restraint, saying bluntly: “Everyone says his d--- was insane, and that he was great sex.” Madonna confirmed it, and Lopez made clear she was not unique: “You’re the third woman to tell me that.”
Authors RoseMarie Terenzio and Liz McNeil, who published the Kennedy Jr. biography “JFK Jr.: An Intimate Oral Biography” in 2024, also claimed in their book that Madonna was not especially significant to him. “She was just a fling. Nothing more than that, barely a fling,” one of his friends said in the book.
The two dated in the late 1980s, when she was still married to Sean Penn and he was also reportedly in a relationship with another woman, actress Christina Haag.
It is also said that John Jr. wanted Madonna to appear on the cover of his magazine — as his mother, Jackie Kennedy.
It is unclear whether Madonna thought it was a little strange that her hot fling wanted her to portray his mother, but she declined.
“Dear Johnny Boy,” she called him teasingly in a fax she sent him, “thank you for asking me to be your mother, but I’m afraid I couldn’t do her justice. First of all, my eyebrows aren’t thick enough. But if you want me to play Eva Braun — I might agree.”
Kennedy Jr. was considered one of America’s hottest bachelors in the 1980s and 1990s, until he met model and publicist Carolyn Bessette, whom he later married. Their relationship, which ended in tragedy, was recently at the center of the series “Love Story” on Disney+.
Madonna, who is currently promoting a new album and a duet with Sabrina Carpenter, has also had quite a few partners, led by her two husbands, Sean Penn and Guy Ritchie. Her résumé also includes several late stars, such as actor Luke Perry and rapper Tupac Shakur, who apparently did not compare to Kennedy in bed.