Madonna Says JFK Jr. Was the Best Sex of Her Life — With One Very Madonna Caveat

Madonna, 67, named John F. Kennedy Jr. as the best sex of her life in a new video made in partnership with Grindr to promote her upcoming 15th studio album Confessions II
When asked to name the “best d***-down” she’s ever had, Madonna offered a qualifier first: “I’m only going to name dead people” — then picked JFK Jr., with whom she had a brief relationship in the early 1990s
The video was obtained early by Page Six and also features playwright Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and i-D’s Marcello Gutierrez
Confessions II is the follow-up to Madonna’s 2005 album Confessions on a Dance Floor; no release date has been announced

Madonna has never exactly been tight-lipped about her personal life, but her latest disclosure comes with one of her better qualifiers in recent memory. In a new video made with Grindr to promote her upcoming album Confessions II, the 67-year-old was asked to name the best sex she’s ever had. She was happy to answer — on one condition.

“I’m only going to name dead people,” Madonna said. Then she named John F. Kennedy Jr., per Page Six, which obtained the video before its release.

Madonna and Kennedy Jr. had a brief relationship in the early 1990s — a pairing that was the subject of considerable tabloid attention at the time and has been referenced in the decades since. Kennedy Jr. died in a 1999 plane crash at 38. The caveat Madonna attached to her ranking — limiting it to deceased exes — was noted across coverage as both practical and characteristically Madonna: a way of answering the question while declining to compare anyone currently living.

The Confessions II Rollout

The Grindr collaboration is part of an unconventional promotional push for Madonna’s 15th studio album, the follow-up to her landmark 2005 record Confessions on a Dance Floor. Instead of a traditional press tour, she filmed a roundtable-style video with playwright Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and i-D Global Beauty Editor Marcello Gutierrez — a mix of queer artists and tastemakers suited to the Grindr platform, per Us Magazine.

The questions in the video ranged from playful to pointed. The JFK Jr. answer has naturally dominated the coverage since the clip began circulating Thursday, per Just Jared. No release date for Confessions II has been announced.