Madonna Reveals John F. Kennedy Jr. as Her Best Lover in Candid Video

Madonna opened up about her romantic past while filming a video in collaboration with Grindr to promote her forthcoming album Confessions II.

The pop icon appeared alongside Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and i-D Global Beauty Editor Marcello Gutierrez for the candid conversation.

When asked about her best sexual experience, Madonna set a boundary for her response. "I'm only going to name dead people," she said before whispering "John Kennedy Jr." as those present reacted with audible surprise.

Designer Raul Lopez chimed in with his own commentary, noting that others had made similar claims about the late Kennedy heir. "Everyone says his d–k was crazy and he was a good f–k," he remarked, to which Madonna responded affirmatively.

Lopez added that Madonna was the third person he'd heard express this sentiment about JFK Jr.

The two reportedly shared a brief romantic connection during the late 1980s. According to the 2024 book JFK Jr.: An Intimate Oral Biography, their involvement was described as fleeting—Madonna was married to Sean Penn at the time, while Kennedy was dating Christina Haag.

"Nothing more. Barely a fling at that," the book stated.

RoseMarie Terenzio, who served as JFK Jr.'s assistant and co-authored the biography, recalled an idea Kennedy had involving Madonna. He envisioned her posing for the cover of his political magazine George, dressed as his mother in a suit, signature sunglasses, and a pillbox hat positioned atop a stack of books.

Madonna declined the concept, reportedly responding with a handwritten note: "Dear Johnny boy, Thanks for asking me to be your mother, but I'm afraid, I could never do her justice. My eyebrows aren't thick enough for one."

The video drops as Madonna gears up for a major performance, with organizers offering minimal details about what fans can anticipate.