Madonna has never been shy about her high-profile love life, but even longtime fans were stunned by her latest jaw-dropping confession about John F. Kennedy Jr. The Queen of Pop, 67, revealed that JFK Jr. was the best lover she had ever had while reflecting on their brief late-1980s romance.
At the time, Madonna was riding high on the success of her critically acclaimed album Like a Prayer and was still technically married to actor Sean Penn. Meanwhile, JFK Jr. was working as an assistant district attorney in Manhattan and was linked to model Christina Haag. Though their romance was short-lived, it appears the fling left quite the lasting impression on the Material Girl singer.
During a candid interview for Grindr promoting her upcoming album Confessions II, Madonna made the astonishing revelation after being asked by designer Raul Lopez, according to Page Six: 'Who was your best d**k down?'
'I'm only going to name dead people,' Madonna exclaimed, before covering her mouth and whispering: 'John Kennedy Jr.' The rest of the interview panel - which included playwright Jeremy O. Harris, Bob the Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and Interview magazine's Marcello Gutierrez - appeared visibly stunned by the confession, according to the outlet.
Lopez then quipped: 'Everyone says his d**k was crazy and he was a good f***.' Madonna appeared to agree, responding with a knowing: 'Mmm hmm.' 'You're the third person I've heard say that,' Lopez replied.
As fans know, both stars eventually moved on with other partners following their brief romance. JFK Jr. famously married Carolyn Bessette-Kennedy in 1996, while Madonna went on to tie the knot with filmmaker Guy Ritchie in 2000 before the pair divorced eight years later. Most recently, the Like a Virgin singer has been linked to Akeem Morris, who is 38 years her junior.
Between JFK Jr. and Morris, however, Madonna's dating history included a string of glamorous romances with stars such as Warren Beatty, Tupac Shakur, Dennis Rodman, and Alex Rodriguez. Still, it appears the late Kennedy heir - who died alongside his wife and sister-in-law in a 1999 plane crash - was particularly captivated by the pop icon.
'For his part John, who was not above being star struck, was dazzled by the notion of dating Madonna,' The Day John Died author Christopher Anderson wrote. 'The most glamorous, celebrated, and, by all accounts, exciting woman of her generation.' 'You could see it in his eyes that first time they met,' dancer Erika Belle, one of Madonna's closest friends at the time, added in Anderson's biography. 'John was totally in awe.'
Another biography, however, claimed the fascination may have gone both ways. 'She came on to him and it was flattery,' a friend alleged in Liz McNeil and RoseMarie Terenzio's 2024 book An Intimate Oral Biography.
While neither Madonna nor JFK Jr. ever publicly explained why the relationship fizzled out, reports later suggested his mother, former First Lady Jacqueline Kennedy Onassis, was less than thrilled by the romance. '[Jackie's] problem with [Madonna] was that she was married,' Jackie: Public, Private, Secret author J. Randy Taraborrelli told People. The journalist added that Onassis was also 'confounded by Madonna's penchant for attention. Jackie had spent her entire celebrity life avoiding paparazzi, whereas Madonna would court paparazzi. And Jackie just couldn't understand any of that.'
According to Taraborrelli, Onassis even attended one of Madonna's performances incognito. '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,' he recalled. '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.”' Taraborrelli added: 'She thought Madonna was good in the show. But she also felt like she didn't want to validate the relationship that John had with Madonna by being photographed.'
Despite the rumored family tensions, there appeared to be no bad blood between Madonna and JFK Jr. According to JFK Jr.: An Intimate Oral Biography co-author RoseMarie Terenzio, the publisher later invited Madonna to pose for the cover of his magazine George styled as his mother. 'John had this idea of having Madonna pose on the cover as his mom,' Terenzio said, per People. 'We would dress her in a suit, her signature sunglasses. And a pillbox hat sitting on a stack of books.'
Madonna ultimately declined the offer, but not without a sense of humor. 'Dear Johnny boy,' she reportedly wrote via fax. '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.'
Madonna's startling confession comes just weeks after Brooke Shields also reflected on her own brief romance with JFK Jr. nearly four decades later. The 60-year-old actress was linked to the late Kennedy heir in the late 1980s after the pair met during a skiing trip in Aspen, Colorado, when Shields was still in her early twenties and starring in films such as Endless Love and Sahara. While appearing on Watch What Happens Live with Andy Cohen, the Pretty Baby star confirmed the two had indeed 'dated' - though she insisted the relationship never became physical. 'I didn't have a love story, I had a crazy, crazy crush,' Shields admitted. She then addressed the inevitable question of whether the pair ever slept together. 'We dated but I never slept with him so I don't know if that counts ... He was lovely to me.'
