June 15, 2026
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Jack Schlossberg had a very cringey response to Madonna’s raunchy comments about his late uncle, John F. Kennedy Jr.

The son of Caroline Kennedy, JFK Jr.’s sister, reacted to Madonna calling the late George Magazine founder the best sex of her life while appearing on Tuesday’s episode of SiriusXM’s “Radio Andy.”

“Here’s a random question. When you hear someone like Madonna say, ‘JFK Jr. was the best sex I ever had.’ Do you chuckle at that?” host Andy Cohen asked Schlossberg.

Jack Schlossberg (seen here in May) reacted to Madonna claiming his late uncle, John F Kennedy Jr., was the best sex of her life. Getty Images
Madonna (seen here with JFK Jr. in 1997) recently said that he was her best hookup. GTRES / Shutterstock

The grandson of President John F. Kennedy — who is currently running for Congress — awkwardly paused, prompting the Bravo bigwig to call him out.

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“He’s running for office, so he’s trying to figure out what to say,” Cohen joked.

Schlossberg, 33, confirmed that he was, indeed, seeking a seat in the U.S. House of Representatives before addressing Cohen’s inquiry.

“All I can say is that, I bet she was right,” Schlossberg said.

Schlossberg (seen here in March) appeared on SiriusXM’s “Radio Andy” Tuesday, when he was asked about the pop star’s comments. Gregory P. Mango for NY Post
“All I can say is that, I bet she was right,” Schlossberg (seen here in June) said. Diane Cohen / BACKGRID

Madonna partnered with Grindr while promoting her new album, “Confessions II,” and answered some questions, including, “Who was your best d–k down?”

“I’m only going to name dead people,” Madonna said, before whispering, “John Kennedy Jr.”

“He had a really fun time and a really good time [with Madonna],” the source divulged, adding that they only hooked up once.

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A source told Page Six last month that their hookup was a “fun adventure” for JFK Jr. (seen here with Madonna in 1997). Getty Images
Madonna (seen here in 2025) dubbed him the best sex ever last month. madonna/Instagram

“I just remember him saying that it was like a whirlwind little romance, but it didn’t really go further,” Terenzio said, adding, “And I know that there were a lot of scheduling issues involved because she was on tour.”

The author of “Fairy Tale Interrupted: A Memoir of Life, Love, and Loss” also claimed that they “friend-zoned each other” and “both just kind of moved on.”

However, they maintained a flirty friendship and would often send cheeky notes to each other via fax machine.

“They had a really cute banter and a nice friendship,” Terenzio said. “They didn’t see each other all the time or anything like that. But they had a cute, funny friendship.”

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Kennedy Jr. went on to marry Carolyn Bessette Kennedy (seen together here in 1999). Getty Images
The couple (seen here in 1995) died in a plane crash in 1999. Getty Images

JFK Jr. ultimately married Carolyn Bessette in 1996, but they tragically died in a plane crash three years later. He was 38, and she was 33.

“He’s working every day,” our source shared. “People meet him and may want to date him, but they definitely want to vote for him. His date spots would include senior centers, picket lines, churches and temples.”

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