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Live the Gossip > Lifestyle > Jack Schlossberg Weighs In on Madonna's NSFW Comments About Dating JFK Jr.
Lifestyle

Jack Schlossberg Weighs In on Madonna's NSFW Comments About Dating JFK Jr.

Written by: News Room Last updated: June 9, 2026
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The congressional candidate sat down for SiriusXM's 'Andy Cohen Live' to chat about his campaign and family when a shocking question was thrown his way

Jack Schlossberg (left); Madonna with JFK Jr. in 1997 (right)
Credit: Roy Rochlin/Getty; GTRES/Shutterstock

NEED TO KNOW

  • Andy Cohen asked Jack Schlossberg for his thoughts on Madonna’s claim that his late uncle, JFK Jr., was the “best sex” she ever had
  • Schlossberg, who appeared on SiriusXM’s Andy Cohen Live to discuss his congressional campaign, tried steering the conversation back on track, but not without sharing a brief thought on the matter
  • The crowded Democratic primary race in New York’s 12th Congressional District is being closely watched as voters prepare to cast their ballots this month, and Schlossberg has positioned himself as the candidate most willing to take on President Donald Trump

Jack Schlossberg found himself in the hot seat on Andy Cohen's podcast with an unexpected question about his late uncle's sex life.

The New York congressional candidate, 33, sat down with Cohen and John Hill for an episode of SiriusXM's Andy Cohen Live. Cohen probed about Madonna's recent comment that Schlossberg's lookalike uncle, John F. Kennedy Jr., was the "best sex" she'd ever had.

"When you hear someone like Madonna say, 'JFK Jr. was the best sex I ever had.' Do you chuckle at that?" Cohen, 58, asked. Schlossberg stuttered before answering. "I'm running for office," he replied, then adding: "All I can say is that I bet she was right."

Madonna and John F. Kennedy Jr. at an event in Las Vegas on June 28, 1997Credit: GTRES/Shutterstock
Madonna and John F. Kennedy Jr. at an event in Las Vegas on June 28, 1997
Credit: GTRES/Shutterstock

Madonna, 67, shared fond memories of her 1980s fling with JFK Jr. in a recent video for the gay dating app Grindr. To celebrate her upcoming Confessions II album, she shared her own confessions alongside Ivy Mugler, Raul Lopez, Jeremy O. Harris, Bob the Drag Queen and Marcelo Gutierrez.

The Queen of Pop asked the group for their thoughts on receiving sexy photos from a partner, the best lighting to set the mood and whether or not size really matters. Then she was asked about the best sex she's ever had.

"I'm going to only name dead people," she said, before whispering: "John Kennedy Jr."

Gutierrez responded that he had heard the same rave reviews of JFK Jr.'s skills in bed. "So you know it's true," the "Like a Prayer" singer said.

Cohen also asked Schlossberg about Kennedy family heirlooms, and whether he has a favorite.

"This is my favorite tie. It's [my grandfather] JFK's tie. I wear it for good luck and today was a big day for me because I am with Andy Cohen. That's the coolest," Schlossberg said. "I have five ties. I only wear five ties ever. This is one of them."

Jack Schlossberg
Jack Schlossberg

The The Watch What Happens Live then wondered whether Schlossberg had inherited any clothing from his late uncle JFK Jr., whose aesthetic is having a moment thanks to FX's hit series Love Story, a dramatized retelling of JFK Jr.'s romance with wife Carolyn Bessette Kennedy.

"I have, like, a watch that doesn't work," Schlossberg said. "He lost most of his clothes apparently. He was given a lot of JFK heirlooms and I think he lost them all."

Sign up for PEOPLE on the Kennedys, our free weekly newsletter where editor-at-large Liz McNeil examines one of America's most famous political dynasties.

Schlossberg, the only grandson of President John F. Kennedy, entered the crowded Democratic primary race for New York's 12th Congressional District after longtime Manhattan-based Rep. Jerry Nadler announced his plans to retire.

Despite getting a few prominent endorsements, including from his mother, Caroline Kennedy, and former House Speaker Nancy Pelosi, he is facing tough competition, including state Assemblyman Micah Lasher, the Democratic establishment's pick; state Assemblyman Alex Bores, the other handsome young progressive in the bunch; and attorney George Conway, the anti-Trump ex-husband of Kellyanne Conway.

Schlossberg has made waves with his no-holds-barred approach to criticizing the Trump administration — including his own cousin, Health Secretary Robert F. Kennedy Jr. — but the most recent poll suggests he has an uphill battle to earning his party's nomination as New Yorkers head to the polls for early voting this week ahead of Election Day on June 23.

Read the full article here

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