Jack Schlossberg’s reaction to Madonna’s recent NSFW comments about John F. Kennedy Jr. was exactly what you would expect.
“Here’s a random question,” Andy Cohen asked Schlossberg, 33, during the Tuesday, June 9, episode of SiriusXM’s Radio Andy. “When you hear someone like Madonna say, ‘JFK Jr. was the best sex I ever had.’ Do you chuckle at that?”
Schlossberg took a bit of a pause before answering the question.
“He’s running for office, so he’s trying to figure out what to say,” Cohen, 58, joked. However, Schlossberg agreed before offering an all-time response.
“I’m running for office,” Schlossberg shared. “All I can say is that, I bet she was right.”
Cohen responded, “That’s a really good answer.”
Madonna, 67, made headlines late last month when teaming up with LGBTQ+ dating app Grindr to promote her upcoming album Confessions II. Fashion designer Raul Lopez asked the legendary singer about her dating life during their unfiltered chat.
“What was your best f***?” he wondered. “Who was your best d***-down?”
Madonna was happy to answer — but wouldn’t name anyone still living.
“Oh, my God. I’m gonna only name dead people,” she said, before whispering, “John Kennedy Jr.”
Lopez wasn’t surprised, explaining that “everybody said [Kennedy’s] d*** was crazy and he was a good f***.” He added, “You’re the third person to say that.”
Madonna briefly dated JFK Jr. in the late 1980s. At the time, her marriage to Sean Penn was fizzling out.
The 2024 biography JFK Jr.: An Intimate Oral Biography offered details into their short-lived fling.
“She came on to him, and it was flattery. She was at the top of her game,” an unnamed friend said in the book. “He loved her body. It was all about physical attraction; it wasn’t going to be anything beyond that.”
While they eventually split, Madonna eventually posed for JFK Jr.’s George magazine in 1996. JFK Jr. famously went on to wed Carolyn Bessette Kennedy that same year.
The couple died three years after their nuptials in a plane crash taking place near Martha’s Vineyard in July 1999. The public’s fascination with their marriage has resurfaced since Ryan Murphy’s FX’s limited series Love Story premiered earlier this year.
Paul Anthony Kelly, who played JFK Jr. in the show, has been upped to heartthrob status after playing the late politician — something his real-life wife is still adjusting to.
“I don’t know if she’s too keen on [it],” Kelly, 37, told Us Weekly exclusively of Syd Widziszewski-Kelly. “She’s very supportive and knows that this was always my dream and is just standing behind me.”
