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    Jack Schlossberg Reacts to Madonna’s NSFW Comments About JFK Jr.

    soreceryBy No Comments13 Mins Read

    Watch: Jack Schlossberg Reacts to Madonna’s NSFW Comments About JFK Jr.

    Jack Schlossberg was a bit flustered by this confession.

    Ahead of the release of Confessions II, Madonna spilled some tea about her storied life and career—including one steamy encounter with Schlossberg’s late uncle John F. Kennedy Jr.

    As for Jack’s reaction to her remarks, he would have preferred not to comment on his uncle’s love life, although Andy Cohen got him to say a few words on the matter. 

    “All I can say is,” he told Cohen during the June 9 episode of Andy Cohen Live, “that I bet she was right.” 

    Before Kennedy died in 1999 alongside his wife Carolyn Bessette Kennedy and her sister Lauren Bessette, he had a bit of a reputation as a ladies’ man in life.  

    And, apparently, Madonna—who previously dated Michael Jackson, Warren Beatty and Sean Penn—can attest. When asked about the best sex she’s ever had, the “Like A Virgin” singer revealed in a recent interview that Kennedy was among the top hookups of her life.

    “Oh, my god,” Madonna admitted during a May 29 Confessions episode with Grindr. “I’m gonna only name dead people. Um, John Kennedy Jr.”

    read

    Madonna Reveals Sex Confession About John F. Kennedy Jr. Romance—With One Caveat

    But the 67-year-old isn’t the only celeb who has praised Kennedy as a lover. Brooke Shields once recalled that the George magazine founder was a great kisser. 

    “He kissed me, and it was like the best kiss I’ve ever had in my life,” Shields told The Howard Stern Show in 2023. “It was beyond not-disappointing. The lips are beautiful, and the face is amazing, and the body and the person, and he was down to earth and funny and irreverent.”

    Roy Rochlin/Getty Images

    After their kiss was mentioned in Love Story, Shields doubled down on her comments in a March 6 TikTok with her daughter Rowan, 23, calling him “one of the best.” 

    Though some celebs are looking back fondly at their memories with JFK Jr. because of Love Story, all of the renewed attention on Kennedy and Bessette Kennedy has inspired mixed emotions for Schlossberg.

    “I’m glad my uncle John was so cool,” the rising politician, who is currently running for Congress, told Next Question With Katie Couric on April 15. “It’s not surprising that people—once they remember who he was—want to dress like him and be like him. He was awesome. He was a smart, attractive person who cared about politics and tried to blend politics and media in his time, just like I’m trying to do right now with social media and politics and our campaign.”

    However, he added, “We have a lot of serious problems facing our country, and my family, we’re not just celebrities. We’re not just icons. These are public servants.”

    Read on to learn about more wild confessions from celebs…

    Michael Tran/AFP via Getty Images

    Apparently, the party doesn’t start until the “Tik Tok” singer puts on her mindfulness playlist.”I actually masturbate to gratitude meditations,” she revealed during a 2026 appearance on Call Her Daddy. “Don’t knock it till you try it.”In fact, Kesha said it’s “amazing” to start the day with guided meditation.”It is OK as a woman to feel pleasure in this world,” she continued. “When you go through things, pleasure is not like the number one neural pathway that your brain always goes to when you have survived things, and I had to reprogram that, and I do it every f–king day and I’m not even embarrassed about it.”

    Michael Tran / AFP via Getty Images

    Nikki GlaserThe comedian shared that she has a “hot husband” fetish, in which she finds pleasure from her partner being in a sexual relationship with other people, with her on-and-off boyfriend Chris Convy.”I didn’t really have a boyfriend before that,” she said on the Call Her Daddu podcast in April 2026, “I would always ask him about past hookups and girlfriends and how they got together. Like, ‘How did you first know you liked each other?’ I loved that.” “It would make me horny to think about him doing that with other girls,” she continued. “So, I’d ask about all of his girlfriends or anyone he had hooked up with, all the details about it and it would really be like a foreplay for me. I would get revved up talking about it.”

    Michael Tullberg/Getty Images

    Pam GrierAt age 76, the Jackie Brown actress said she has orgasms that’ll “last three days.””You don’t have to do anything, but when it happens, I just wanna tell you, you just be prepared,” she quipped to host Julia Louis-Freyfus on a May 2026 episode of Lemonade Media’s Wiser Than Me podcast. “It’s gonna be three whole days.”

    Brandon Nagy/Shutterstock

    Joe JonasThe Jonas Brothers star revealed in 2025 that he had a very embarrassing encounter after he “joined the mile high club a couple years ago,” when he was still married to Sophie Turner.”Left the bathroom, I thought I was high-fiving my drummer,” Joe told the Are You Okay Show on TikTok. “After the high-five, I realized it was the flight attendant.”Since it was a private plane, he said he wouldn’t be “banned from flying,” and admitted that the sex was totally worth the awkward moment.

    Kevin Mazur/Getty Images for Amazon Studios

    Tim GunnThe former Project Runway mentor shared in February 2026 that he has been celibate for more than four decades after a devastating breakup.”One of the things that he told me that night was that he’d been sleeping with just about everything that walked by,” he told Chelsea Handler on her podcast Dear Chelsea. “I had been loyal and faithful to him. He was the only person I’d ever been with. This is the advent of AIDS. It’s 1982.””The self-pity then turned to completely unbridled anger because I thought he may have given me a death sentence,” he continued. “I was tested every six months for ten years for HIV, and thankfully, I had a clean slate.”But whenever he found himself getting closer to someone new, he would be taken back to that traumatizing chapter in his life.”Whenever I was even tempted to engage in something that could become serious with someone,” he reflected, “all this would come back like Niagara Falls, and it would just take the desire away.”

    Kevin Winter/Getty Images for iHeartRadio

    Jelly RollThe country singer confessed in December 2025 that his sex life with wife Bunnie Xo was “horrible” before his 200-lb. weight loss.And it wasn’t because of her, as he noted on the Joe Rogan Experience podcast, “Dude, I married a f–kin’ big-t-tty, blonde, beautiful woman, dawg.”“I married the kind of woman that makes you smile when you’re crying, Joe,” Jelly Roll (real name Jason Bradley DeFord) said. “And I couldn’t even get aroused I was so big. I was having to play Twister to have sex—left foot here, right foot in the X. ‘Are we in there yet? Tell me if you feel something.’ It was bad.”

    Instagram/Brooks Nader

    Brooks NaderTechnically, Brooks’ sister Grace Ann Nader spilled the beans on this one, revealing that the Sports Illustrated model and her Dancing With the Stars partner Gleb Savchenko did more than just rehearse their dance moves behind the scenes.“I can tell you firsthand,” Grace Ann said on the Chicks In the Office podcast in May 2025, “every time I visited Brooks’s trailer, the trailer was shaking every single time. I never wanted to go in there. I was always knocking.”As for Brooks, who had freshly broken up with estranged husband Billy Haire, she joked, “The trailer thing was probably why we didn’t win.”

    Kevin Mazur/Getty Images for SiriusXM

    Brooke ShieldsBrooke got candid about her sex life with husband Chris Henchy in her 2025 memoir Brooke Shields Is Not Allowed to Get Old.“I’m going through all the bodily s–t that comes with aging as a woman even in the best of times,” she wrote in the book, according to People. “The thinning hair and the peach fuzz and the brand-new belly fat and vaginal dryness and the diminishing sex drive—and in my natural state I feel less appealing to him than I ever did before.”Furthermore, she said being intimate can be painful for her now. “For me to fully enjoy sex at this point,” Brooke added, “I need my lotions and potions, the right sleepwear (maybe calling it sleepwear is contributing to the problem), my special pillow, and maybe a tequila so I can relax.”

    (Photo by Udo Salters/Patrick McMullan via Getty Images)

    Katy PerryThe “California Gurls” singer revealed how she thanked ex Orlando Bloom for doing the dishes during their relationship—and it’s not what you’d expect.”If I come downstairs and the kitchen is clean, and you’ve done it all,” Katy told Alex Cooper on a September 2024 episode of Call Her Daddy, “and you’ve done all the dishes, and you’ve closed all the pantry doors, you better be ready to get your d–k sucked.”

    (Photo by ROBERTO SCHMIDT/AFP via Getty Images)

    Chelsea HandlerChelsea is not shy when it comes to sharing her NSFW confessions with the world. In fact, the comedian made headlines when she said a threesome with their masseuse led to her 2010 breakup with Ted Harbert. But after she received a disappointed text from her ex-boyfriend, she had to set the record straight. “I really want to clarify,” Chelsea said on an episode of The Tonight Show Starring Jimmy Fallon in October 2023. “I want to go on the record that that is not why our relationship ended.””We did have a lot of threesomes‚ and that, while that’s private it’s already out there,” she continued, “so I’m gonna double down on that and just say that we didn’t break up because I left him for the masseuse. That didn’t happen.”

    (Photo by Lyvans Boolaky/Getty Images)

    Heidi KlumThere are no skeletons in the America’s Got Talent judge’s closets, but there may be some slightly scandalous fashions.  “It’s a big closet,” she says of the space she’s dubbed her sex closet. “But, there’s outfits in here and things, you know,” she said on The Skinny Confidential Him & Her Show podcast in September 2024. “You can have a lot of things. You can have wigs, you can have outfits, shoes, boots.”She even revealed that her daughter Leni Klum accidentally encountered the space. “She found my sex closet,” Heidi said on an episode of the Call Her Daddy podcast in January 2024. “She fully knew what it was. But, also she was with a friend and she filmed it and they were giggling, and I was like, ‘Oh my God.'”

    (Photo by Swan Gallet/WWD via Getty Images)

    Shailene WoodleyDespite describing herself as a “very sexual person,” Shailene has shared she has some serious “beef” with porn, naming it the “junk food” of pleasure. “The way that sex is presented on the surface in this country is so fabricated,” she said on the She MD podcast in September 2024, “and it’s such a performance instead of true intimacy, vulnerability and connection.””Pleasure is so important, and we just rip each other off of it because I think we don’t necessarily even know what’s possible,” she continued. “And that’s my big beef with porn is I’m like, ‘You’re selling everybody McDonald’s when you could have like, whoa.'”

    (Photo by JC Olivera/Variety via Getty Images)

    Goldie HawnAfter spending four years with partner Kurt Russell, Goldie revealed her biggest secret for a successful, long term relationship. “You have to have good sex,” she told E! News in September 2024. “Because sex is something that connects you and creates more belonging. People who have healthy sexual relationships usually last a lot longer. But it’s not just because of the act, it’s because of the warmth and the intimacy that it creates.”

    (Photo by Kristina Bumphrey/Variety via Getty Images)

    Ice-T revealed the secret to his and Coco Austin‘s decades-long marriage—and yes, it involves the bedroom. “Jungle sex,” he told E! News in January 2024. “That flame has to stay lit.””When that flame goes out and you’re not really attracted to each other anymore,” he continued, “you have to address that very quickly because it’s something that’s necessary.”

    (Photo by Marleen Moise/Getty Images)

    Demi LovatoFor Demi, there’s nothing wrong with feeling confident in the bedroom. “I feel the most confident when I’m having sex,” she told the LadyGang podcast in September 2023. “‘Cause you’re so present that you’re not thinking about what is actually like…what clouds your judgement throughout the rest of the day, or at least that’s how it is for me. It’s not that way for everybody.”

    (Photo by Presley Ann/The Hollywood Reporter via Getty Images)

    Lisa RinnaAfter spending decades with husband Harry Hamlin, Lisa got candid about how aging has affected their sex lives. “I do think that desire levels change for a man,” the actress told Cosmopolitan in January 2024. “That’s just the natural evolution of life. So it’s figuring out how to coexist without taking that personally as a woman. I think that it’s almost more about companionship and about creating space for the ebb and flow of sexuality.””We really have great sex together, and we always have,” she continued. “It’s just that maybe it doesn’t happen quite as often as it did when you’re in your 30s and in your 20s, I would say. And I think that’s normal.”

    (Photo by Arnold Jerocki/FilmMagic)

    Zoe Saldaña & Marco Perego-SaldañaZoe and her husband Marco have created a code word to talk about sex around their kids. “We ‘play Legos naked,'” Marco revealed on The Drew Barrymore Show in April 2024, Zoe chiming in to clarify that the term means “sexy time.”But the couple worried that their older twin boys were catching onto the lingo. “They were like, ‘Are you guys kissing? Are you guys gonna go play naked with your Legos?'” Zoe recounted. “And we’re like, ‘No, we’re not going to do that.'”

    Lia Toby/Getty Images

    Billie EilishThe singer made it one of her goals for 2024 to improve her sex life. Billie—who at the time had sparked romance rumors with Nat Wolff—quipped to that October, “Yes, I’ve had a lot of good sex, so…you’re welcome, Billie!”

    Stephen Lovekin/Shutterstock

    Amy SchumerThe Trainwreck star admitted that using hormone replacement therapy for perimenopause as well as taking a weight-loss medication had some pleasurable side effects in the bedroom with then-husband Chris Fischer.”My hair is fuller, my skin is better,” she said in a March 2025 Instagram video. “I have more energy, I wanna get down more, you know what I mean … I’m talking about sex.”

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