Madonna's Steamy Bedroom Confession — Queen of Pop, 67, Admits John F. Kennedy Jr. Was Her Most Satisfying Lover
Madonna praised late John F. Kennedy Jr.'s skills in the bedroom.
May 28 2026, Published 5:00 p.m. ET
Madonna is spilling the tea on her most satisfying lover – at least out of the list of the ones that are no longer alive, RadarOnline.com can reveal.
While promoting her new album, Confessions II, she teamed up with Grindr and made a video with playwright Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and ID’s Marcello Gutierrez, who all asked her burning questions about her life, her career and her high profile exes.
Madonna's Best (Late) Lover Revealed
Madonna briefly dated John F. Kennedy Jr.
In a video obtained by Page Six, Lopez grilled her on her "best d--k down," she quickly clarified, "I'm only going to name dead people," and then covered her mouth as she whispered, "John F. Kennedy Jr."
After their shocked noises and "shut ups" died down, Lopez added, "Everyone says his d--k was crazy and he was a good f--k."
Madonna replied, "Mmm hmm," seemingly confirming the rumors.
"You’re the third person I’ve heard say that," the clothing designer noted.
Inside Madonna and John F. Kennedy Jr.'s Fling
JFK Jr.'s romance with Madonna was 'nothing more' than a 'fling,' according to a friend.
Madonna and Kennedy Jr. had a brief romance in the 1980s at the height of the Material Girl singer's fame.
"For his part John, who was not above being star struck, was dazzled by the notion of dating Madonna, the most glamorous, celebrated, and, by all accounts, exciting woman of her generation," author Christopher Anderson wrote in his 2000 tell-all The Day John Died.
In JFK Jr.: An Intimate Oral Biography, one of Kennedy Jr.'s pals called the relationship "totally a fling" and "nothing more."
Jackie Kennedy's 'Problem' With Madonna
Madonna filed for divorce from Sean Penn in 1989.
But Kennedy Jr.'s mother, Jackie, had a real "problem" with the short-lived relationship, seeing as the Vogue songstress was technically married to Sean Penn at the time.
The former couple got married in 1985, but Queen of Pop filed for divorce four years later in 1989, citing "irreconcilable differences."
Jackie: Public, Private, Secret author J. Randy Taraborrelli claimed that Jackie was especially "confounded by Madonna's penchant for attention."
"Jackie had spent her entire celebrity life avoiding paparazzi, whereas Madonna would court paparazzi," Taraborrelli told People at the time. "And Jackie just couldn't understand any of that."
Jackie Kennedy 'Didn't Want to Validate the Relationship'
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Jackie Kennedy was confused by Madonna's 'penchant' for public attention.
Jackie was so desperate to avoid unnecessary attention that she went so far as to put on disguises in public – though they didn't particularly work, according to the writer.
"I interviewed somebody who worked with Jackie at Doubleday, who said that she went with Jackie to the show; that Jackie wore a red wig so that she wouldn't be recognized," Taraborrelli continued. "She put the wig on, and she asked this woman, 'How do I look?' And the woman said, 'You look just like Jackie Onassis in a red wig.'"
"She thought Madonna was good in the show," the author added. "But she also felt like she didn't want to validate the relationship that John had with Madonna by being photographed."
