Jack Schlossberg weighs in on Madonna's confession that dead uncle was ‘best sex ever’
Jack Schlossberg has reluctantly weighed in on John F Kennedy Jr's alleged skills in the bedroom, after Madonna revealed his late uncle was the best sex she'd ever had.
The only son of former US President JFK was introduced to younger generations earlier this year through FX drama series Love Story, and now he's back in the headlines for another reason – being the best shag Madonna ever had.
Which I imagine wasn't a sentence you'd expected to hear at the start of 2026.
The Queen of Pop made the admission during a Q&A with Grindr, when fashion designer Raul Lopez asked her: "What was your best f**k? Who was your best d**k-down?"
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Not wanting to cause controversy, Madonna opted to exclude any living sexual partners from the conversation, replying: "I’m only going to name dead people... John Kennedy Jr."
Marcelo Gutierrez then weighed in to say that he'd also heard rave reviews about the younger Kennedy, to which the 67-year-old replied: "So you know it's true."
Which is certainly a glowing recommendation for JFK Jr's bedroom skills.
Now the late attorney's nephew has been asked to weigh in on the matter, with the revelation being put to Schlossberg during an appearance on SiriusXM's Andy Cohen Live to discuss his upcoming congressional campaign.
"When you hear someone like Madonna say, 'JFK Jr. was the best sex I ever had.' Do you chuckle at that?" Cohen enquired.
The question clearly caught Schlossberg off-guard, with the 33-year-old stuttering before replying: "I'm running for office."
However, Schlossberg didn't dodge the question entirely, cheekily adding: "All I can say is that I bet she was right."
So there you have it, JFK Jr was (allegedly) a top shagger.
Did JFK Jr date Madonna?
According to a friend of JFK Jr, he did have a romantic relationship with the 'Like a Prayer' singer, but it was apparently only a brief fling.
"Madonna was totally a fling," one of Kennedy's close pals said. "Nothing more. Barely a fling at that."
Apparently, the pair crossed paths in the 1980s, when Madonna was still married to then husband Sean Penn, while Kennedy was dating actress Christina Haag.
However, it didn't stop the singer from shooting her shot, with JFK Jr biographers Rosemarie Terenzio and Liz McNeil writing: "She came on to him, and it was flattery. She was at the top of her game,” the book's authors wrote.
"He loved her body. It was all about physical attraction; it wasn’t going to be anything beyond that."
Madonna and Haag weren't the only celebrities with whom JFK Jr had romantic entanglements, as he also dated Kill Bill star Daryl Hannah before ultimately marrying Carolyn Bessette.
The couple's lives would be tragically cut short in 1999, when the couple, as well as the Calvin Klein publicist's singer Lauren Bessette, died in a plane crash.
Topics: Celebrity, John F. Kennedy, Sex and Relationships, Madonna
Brenna Cooper