Jack Schlossberg had the only answer he could safely give after Andy Cohen asked him about Madonna’s eye-popping claim that John F. Kennedy Jr. was the best sex of her life.
Cohen put Schlossberg on the spot during the latest “Radio Andy” episode, bringing up Madonna’s newly revived JFK Jr. bedroom story.
The Madonna comment came out during a Grindr-backed discussion about sex, intimacy and her upcoming “Confessions II” album.
Pressed for her most memorable bedroom partner, Madonna set one ground rule before giving the room a Kennedy shocker.
“I’m only going to name dead people,” Madonna said before whispering, “John Kennedy Jr.”
The admission reportedly stunned the room, prompting someone to respond, “Shut up!”
That set up Cohen’s question to Schlossberg. “Here’s a random question. When you hear someone like Madonna say, ‘JFK Jr. was the best sex I ever had,’ What do you… do you chuckle at that?” Cohen asked on the latest episode of his radio show.
Schlossberg did not exactly rush into an answer. “I want, uh… I, it does…mmm,” he said, fumbling through the moment.
Cohen jumped in with a save, noting that Schlossberg is now running for office.
“He’s running for office, so he’s trying to figure out what to say,” Cohen said.
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Then Schlossberg found the line. “All I can say is that, um, I bet she was right!” he quipped.
Cohen immediately approved. “Yeah, right! There you go. That’s a good answer. That’s a really good answer!”
The exchange came amid renewed fascination with JFK Jr.’s love life after the release of Ryan Murphy’s “Love Story,” which dramatizes Kennedy’s relationship with Carolyn Bessette before the couple died in a 1999 plane crash.
During Madonna’s Grindr event, designer Raul Lopez was among the media personalities taking part in the conversation.
After the singer named Kennedy, another participant, Gutierrez, said she had heard from multiple people that the George magazine founder was great in bed.
“So you know it’s true,” Madonna replied.
The “Radio Andy” conversation later moved from tabloid lore to Kennedy keepsakes.
Around Schlossberg’s neck was one of his grandfather’s ties, which he said he saves for good luck.
“This is my favorite tie. It’s JFK’s tie. I wear it for good luck and today was a big day for me because I am with Andy Cohen, okay, who is the coolest!” Schlossberg remarked.
He added that he only rotates among five ties. Cohen asked whether he had any ties that belonged to his uncle.
Schlossberg said he had “a watch that doesn’t work” from JFK Jr., then suggested his uncle had not done the best job preserving inherited items.
He said JFK Jr. had been given “a lot of like JFK heirlooms,” but “lost most of his clothes, apparently” and “he lost them all.”
Kennedy’s romantic history had already resurfaced on Cohen’s turf earlier this year, when Brooke Shields revisited her brief connection to him.
During a May appearance on “Watch What Happens Live,” Cohen asked Shields whether she and Kennedy had their own “love story.”
“We dated, but I never slept with him. I don’t know if that counts,” she told the host. “It counted for me!”
Shields still described their meeting warmly. “He was lovely to meet,” she added.
Their brief media-fueled connection began after they crossed paths at an Aspen ski resort in the 1980s.
In a 2023 interview with Howard Stern, Shields said Kennedy told her she “looked like his mother,” former first lady Jacqueline Kennedy Onassis.
That same trip later produced what Shields called “the best kiss I’ve ever had in my life.”
“The lips are beautiful, the face is amazing, and the body and the person,” Shields stated.
Shields told Cohen she enjoyed “Love Story” and “thought the acting was amazing.”
Not every Kennedy ex was as charmed by the series.
In March, Daryl Hannah wrote an essay in The New York Times ripping the Ryan Murphy project as “tragedy-exploiting” and “textbook misogyny.”
“It’s appalling to me that I even have to defend myself against a television show,” Hannah wrote.
“These are not creative embellishments of personality. They are assertions about conduct — and they are false.”
Away from JFK Jr. nostalgia, Schlossberg is trying to turn his own online persona into a congressional campaign asset.
In a separate CBS New York interview, he said President Donald Trump’s ability to shape the national conversation through social media is a kind of political genius, even though he does not admire the president.
“I don’t admire President Trump for anything, but I deeply, deeply respect and recognize his genius in the way that he programs all of what we talk about every day,” Schlossberg said. “He programs our minds.”
He noted that Trump’s words dominate the conversation after he posts or speaks.
“He says things, and we end up repeating them all day long. He’s living in all of our heads right now. And it’s terrible, but it is powerful,” Schlossberg continued.
“And it is the one way to wield power now. And we don’t really have an option not to compete out there.”
His pitch to Democrats was simple: meet voters where the fight is already happening.
“I do that the way that Democrats in the past have always used new media, which is to celebrate and get the information out about the things that we stand for because we should be proud of it,” Schlossberg suggested.
“We should use our humor, our intellect. We should not be afraid to take risks.”
He said candidates have to be authentic rather than hiding from public scrutiny.
“And the way that I do that is not going to be the same as the way another candidate does that. It’s about being authentic to who you are and letting people into your world,” he told the outlet.
“The other candidates I’m running against, they want you to look away. I want you to look at everything that I’m doing because I’m proud of it and thinking about it, and I’m working 24/7.”
Schlossberg is one of several Democrats running to replace Rep. Jerry Nadler in New York’s 12th Congressional District.