Jack Schlossberg Awkwardly Responds to Madonna's Confession His Uncle JFK Jr. Was Her 'Most Satisfying' Lover in Bed — 'I Bet She Was Right'
Jack Schlossberg found himself answering questions about his late uncle's dating history during a SiriusXM appearance.
June 9 2026, Published 4:00 p.m. ET
Jack Schlossberg was left squirming when Andy Cohen put him on the spot about one of Madonna's most eyebrow-raising confessions, RadarOnline.com can reveal.
The Kennedy heir, who recently launched a bid for Congress, struggled to answer after the TV host asked him about the Queen of Pop's claim that his late uncle, John F. Kennedy Jr., was the best lover she'd ever had.
'I Bet She Was Right'
Andy Cohen asked the congressional candidate about Madonna's recent comments regarding JFK Jr.
Appearing on SiriusXM's Andy Cohen Live, Schlossberg, 33, was asked whether he laughs when he hears celebrities discuss his famous uncle's romantic reputation.
Cohen referenced Madonna's recent revelation that JFK Jr. was the "best s-x" she'd ever experienced and asked for Schlossberg's reaction.
Caught off guard, the aspiring politician initially tried to dodge the question.
"I'm running for office," he replied before adding with a nervous laugh: "All I can say is that I bet she was right."
Madonna recently named JFK Jr. as the most satisfying lover she has ever had.
Madonna's Surprising Confession
The singer made the revelation while participating in a candid video promoting her new album.
The awkward exchange came just days after Madonna made the revealing confession while promoting her upcoming album, Confessions II, in a video collaboration with Grindr.
Asked about the best s-x she'd ever had, the iconic singer teased: "I'm only going to name dead people."
She then covered her mouth and whispered: "John Kennedy Jr."
After the group erupted in shock, designer Raul Lopez told her: "Everyone says his d--k was crazy, and he was a good f--k."
Madonna appeared to confirm the reputation, responding simply: "Mmm hmm."
Lopez then added: "You're the third person I've heard say that."
A Short-Lived Romance
Madonna and JFK Jr. briefly dated during the 1980s when both were major cultural figures.
Madonna and JFK Jr. were romantically linked during the late 1980s when both were among the biggest names in America.
Author Christopher Anderson later wrote in The Day John Died: "For his part, John, who was not above being star-struck, was dazzled by the notion of dating Madonna, the most glamorous, celebrated, and, by all accounts, exciting woman of her generation."
However, in JFK Jr.: An Intimate Oral Biography, one of JFK Jr.'s friends described the relationship as "totally a fling" and "nothing more."
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Treasured Kennedy Keepsakes
Schlossberg later revealed his favorite Kennedy family heirloom is one of President John F. Kennedy's ties.
The conversation eventually shifted away from Madonna's bombshell comments and toward Schlossberg's famous family history.
Asked whether he had a favorite Kennedy heirloom, Schlossberg pointed to the tie he was wearing during the interview.
"This is my favorite tie. It's [my grandfather] JFK's tie," he said. "I wear it for good luck, and today was a big day for me because I am with Andy Cohen. That's the coolest."
The congressional hopeful added, "I have five ties. I only wear five ties ever. This is one of them."
Cohen then wondered whether Schlossberg had inherited any items from his late uncle:
"I have, like, a watch that doesn't work," Schlossberg admitted. "He lost most of his clothes, apparently. He was given a lot of JFK heirlooms, and I think he lost them all."
