Madonna appears in a promotional video for her new album Confessions II, saying she would "only going to name dead people" when asked to name her best-ever sexual partner — and then answering simply, "John Kennedy Jr."
The clip, part of a collaboration with Grindr that features Jeremy O. Harris, Bob The Drag Queen, Ivy Mugler, Raul Lopez and Marcello Gutierrez, was previewed to Page Six the Thursday before it appeared in coverage tied to a Daily Beast story. In the exchange, Lopez asks, "Who was your best d–k down?" and follows with, "Everyone says his d–k was crazy and he was a good f–k." Madonna replies, "Mmm hmm."
The name Madonna gave — John F. Kennedy Jr. — is not new to her own history. Kennedy, who died at age 38 in a 1999 plane accident with his wife Carolyn Bessette, was briefly involved with Madonna in the late 1980s. The relationship has been documented in recent books and profiles about JFK Jr., which characterize the pair’s involvement as short and primarily physical.
A 2024 oral biography, JFK Jr.: An Intimate Oral Biography, recounts that the two met while Kennedy was dating actress Christina Haag and Madonna was married to Sean Penn. An unidentified Kennedy friend told the book, "Madonna was totally a fling" and added, "Nothing more. Barely a fling at that." The same source said, "She came on to him, and it was flattery. She was at the top of her game" and that "it was all about physical attraction, it wasn’t going to be anything beyond that."
The book also addresses precautions and behavior: it reports that the pair did not use "the protection measures" and that Madonna was nevertheless "very on top of HIV prevention," noting that they instead "had fun in other ways." A line attributed to Kennedy in the material says Madonna had "one of the most beautiful bodies he had ever seen." J. Randy Taraborrelli, in After Camelot, wrote that Kennedy once gave Madonna a set of keys to his apartment and suggested the relationship unsettled Jackie Onassis because of Madonna’s paparazzi-seeking behavior.
Madonna was 67 in the Daily Beast piece that carried the promotional clip; she was still married to Sean Penn until January 1989, according to the timeline in those books. The new video is being used to promote Confessions II as part of a wider marketing push with Grindr, and it places an intentionally provocative anecdote — naming a dead public figure — at the center of that push.
The tension in the moment is twofold. One thread is factual: the account Madonna chose to amplify aligns with decades-old material that frames the encounter as brief and sexual rather than romantic. The other is ethical and cultural: invoking a deceased, widely known public figure as a sexual benchmark both refreshes public curiosity about his private life and confronts how memory, fame and consent intersect when one party can no longer respond.
What happens next is straightforward. Madonna’s one-line answer confirms a detail long reported in biographies and oral histories; it does not alter the established record about John F. Kennedy Jr.’s life or death, but it will almost certainly redirect attention back to the books and sources that described the late-1980s fling. For Madonna, the comment serves the immediate purpose of a provocative promotional moment in the Confessions II campaign; for the public, it is a reminder that tabloid-era encounters can resurface as marketing in a later era.
