Madonna has opened up about her short-lived romance with JFK Jr., prompting a response from his nephew, Jack Schlossberg.
Schlossberg appeared on SiriusXM’s “Andy Cohen Live,” where he was surprised when Cohen shared a statement from the Material Girl about her relationship with his uncle. However, he responded in real time as Cohen relayed her NSFW commentary.
Madonna’s Intimate Admission Stunned JFK Jr.’s Nephew
During an appearance on Andy Cohen Live’s Radio Andy, Jack Schlossberg was surprised when the host asked him for commentary on Madonna’s remarks regarding his late uncle, JFK Jr.
“When you hear someone like Madonna say, ‘JFK Jr. was the best s** I ever had.’ Do you chuckle at that?” Cohen asked. However, Schlossberg was initially hesitant with his response.
He stated, “I’m running for office.” But then, he added, “All I can say is that I bet she was right.”
Schlossberg is the only son of Kennedy’s sister, Caroline Kennedy Schlossberg, and her husband, Ed. His sister, Tatiana, passed away in December 2025 after a battle with acute myeloid leukemia.
The political figure was only 6 years old when Kennedy Jr. perished in a plane crash in July 1999. His wife, Carolyn Bessette Kennedy, and her sister, Lauren Bessette, were on board as well.
Cohen’s question was prompted by Madonna’s appearance in a YouTube video for the dating app Grindr. She was asked about the best intimate relationship she ever had. The entertainer named the Kennedy heir, whom she briefly dated in 1988.
The Material Girl responded, “I’m going to only name dead people. John Kennedy Jr.”
How Long Did Madonna and JFK Jr. Date?
GettyMadonna and John F. Kennedy Jr. dated briefly in the late 1980s.
According to In Style, they became a couple after she ended her marriage to Sean Penn.
The publication quoted author Christopher Anderson, who penned the book “The Day John Died.” He stated, “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.”
In a separate book, “JFK Jr.: An Intimate Oral Biography” by Liz McNeil and RoseMarie Terenzio, the authors claimed that even after their brief fling ended, John and Madonna continued to stay in touch. He reportedly asked her to pose for the cover of his magazine, George. The publication featured celebrities as key political figures or commenting on political situations.
“John had this idea of having Madonna pose on the cover as his mom,” Terenzio said, in a book excerpt published by PEOPLE Magazine. “We would dress her in a suit, her signature sunglasses. And a pillbox hat sitting on a stack of books.”
However, Madonna didn’t go for the idea. She responded via fax, “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.”
Shortly after his fling with Madonna, Kennedy met Carolyn Bessette. The couple married in September 1996. Their relationship was depicted in the FX Series “Love Story.”
