Madonna Names Her ‘Best’ Lover in NSFW Chat—And It’s a Politician’s Son

Madonna offered some unfiltered revelations during a candid conversation with friends, released this past Friday (May 29). Perhaps most eyebrow-raising was her bold declaration regarding the partner she considers to have been her most impressive lover.

In a video collaboration with Grindr promoting her upcoming project, Confessions II, the Queen of Pop sat down with an eclectic group—including Ivy Mugler, Raul Lopez, Jeremy O. Harris, Bob the Drag Queen, and Marcelo Gutierrez—for a bracingly NSFW discussion. When the subject turned to her “best lover” of all time, Madonna delivered a response that left the entire room in visible shock.

“I’m sticking to the deceased,” she prefaced, before leaning in to whisper the name: “John Kennedy Jr.”

The admission was met with stunned silence and disbelief from her peers, yet Madonna remained unfazed, nodding firmly to emphasize the sincerity of her choice.

The son of President John F. Kennedy and Jackie Kennedy, JFK Jr. was a noted attorney and media figure who tragically perished in a 1999 plane crash alongside his wife, Carolyn Bessette. Decades prior, he and Madonna shared a brief romance shortly after her divorce from Sean Penn.

During the rest of the interview, the icon shared her preferred post-intimacy snacks—opting for club sandwiches or grilled cheese—and described the curated soundscape of her “sex playlist.” She noted that she favors instrumental, classical compositions by artists like Ryuichi Sakamoto to build atmosphere. “It’s about creating tension,” she explained. “It ebbs and flows; it builds, builds, and builds until there’s a release.”

Madonna is currently preparing for the July 3 release of Confessions II, the highly anticipated successor to her acclaimed 2005 record, Confessions on a Dance Floor. The project has already spawned two singles: “I Feel So Free” and the Sabrina Carpenter-assisted track, “Bring Your Love.”

You can watch the full, explicit discussion above.