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

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Jack Schlossberg was a bit flustered by this confession.

Before her album Confessions II comes out, Madonna shared some surprising details about her life and career, including a romantic experience with the late John F. Kennedy Jr., the nephew of Victor Schlossberg.

Jack wasn’t eager to discuss his uncle’s relationships, but Andy Cohen managed to get him to share a little bit about it.

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

Before his death in 1999, John F. Kennedy Jr. was known for dating many women. He died in a plane crash along with his wife, Carolyn Bessette Kennedy, and her sister, Lauren Bessette.

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.

During a recent conversation on the Grindr podcast ‘Confessions,’ Madonna jokingly stated she would only mention people who are no longer alive, and immediately referenced John F. Kennedy Jr. as an example.

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. 

In a 2023 interview with The Howard Stern Show, Shields described a kiss with someone as the best she’d ever experienced. She raved about his attractive features – beautiful lips and an amazing face – as well as his personality, calling him down-to-earth, funny, and playfully rebellious.

Following a reference to their kiss in the movie Love Story, Brooke Shields reaffirmed her positive feelings about Michael Jackson in a TikTok video posted on March 6th with her daughter, Rowan, 23, describing him as “one of the best.”

While some celebrities are remembering John F. Kennedy Jr. with fondness, especially because of the movie Love Story, the recent focus on Kennedy and his wife, Carolyn Bessette Kennedy, has stirred up complicated feelings for their daughter, Rose Schlossberg.

The politician, who is campaigning for Congress, recently told Katie Couric that he admired his uncle John. He explained that it’s understandable people are now inspired by his uncle’s style and personality. He described his uncle as intelligent, charismatic, and passionate about combining politics and media – something the politician is now also trying to achieve through social media and his campaign.

He also emphasized that while his family may be well-known, they are, first and foremost, people dedicated to serving the public and addressing the serious issues facing the nation.

Read on to learn about more wild confessions from celebs…

Apparently, the party doesn’t start until the “Tik Tok” singer puts on her mindfulness playlist.

Okay, so this is a little unexpected, but I’m sharing something I learned that really works for me! I actually find that incorporating gratitude meditations into my self-care routine is incredibly satisfying. I know it sounds unusual, but trust me – it’s a game changer. Seriously, give it a try before you judge!

In fact, Kesha said it’s “amazing” to start the day with guided meditation.

She explained that women are allowed to enjoy pleasure. She admitted that after difficult experiences, it’s not natural to immediately think of pleasure, and she’s actively worked to change that. She does this daily and feels no shame about it.

The comedian revealed she’s attracted to the idea of her partner having sexual relationships with others – a preference she specifically associates with her boyfriend, Chris Convy. She described this as a ‘hot husband’ fetish.

She explained on the Call Her Daddu podcast in April 2026 that she hadn’t had a boyfriend before him. She used to be really curious about his past relationships, always asking him how he met his exes and how things started. She admitted she ‘loved’ hearing those stories, like asking, ‘How did you realize you liked each other?’

She admitted that hearing about his past relationships was sexually exciting for her. She’d ask for details about his ex-girlfriends and casual encounters, finding the conversation itself to be arousing and a way to build anticipation.

At age 76, the Jackie Brown actress said she has orgasms that’ll “last three days.”

I was really struck by something the guest said to Julia Louis-Dreyfus on the Wiser Than Me podcast back in May 2026. She playfully warned listeners to just be ready, because whatever ‘it’ is, it’s going to last a full three days! It felt like a little inside joke, but also a surprisingly practical piece of advice.

In 2025, Jonas Brothers member Joe Jonas admitted to a mortifying experience from a couple of years prior: he had an intimate encounter on a flight while 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.

The well-known fashion mentor, formerly of Project Runway, revealed in February 2026 that he hasn’t been in a relationship for over forty years, following a painful split.

He confessed to Chelsea Handler on her podcast, Dear Chelsea, that he’d been having many casual sexual encounters. He explained this happened around 1982, a time when the AIDS epidemic was just beginning, and revealed he had been completely faithful to him, being the only person he’d ever been with.

“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.”

Whenever he started to connect with someone, he’d be reminded of a painful experience from his past.

You know, whenever I even thought about getting seriously involved with someone, this overwhelming feeling would rush back – it was like being hit by Niagara Falls! It instantly killed any romantic interest I had. It always reminded me of everything, and it was just too much to handle, so I’d back away.

In December 2025, the country singer revealed that his relationship with his wife, Bunnie Xo, suffered from intimacy issues before he lost 200 pounds.

He explained on the Joe Rogan Experience podcast that it wasn’t his wife’s fault, saying, “I married an incredibly attractive, blonde woman.”

“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.”

Brooks’ sister, Grace Ann Nader, let it slip that the Sports Illustrated model and her Dancing With the Stars partner, Gleb Savchenko, had a romantic connection beyond their dance practice.

In May 2025, on the Chicks In the Office podcast, Grace Ann shared that whenever she went to visit Brooks’s trailer, it would shake. She admitted she didn’t like going inside and always knocked first.

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.”

Brooke got candid about her sex life with husband Chris Henchy in her 2025 memoir Brooke Shields Is Not Allowed to Get Old.

She shared in her book, as reported by People, that she’s experiencing the typical physical changes that come with aging as a woman, like hair thinning, unwanted facial hair, new belly fat, vaginal dryness, and a decreased sex drive. She also expressed feeling less attractive to her partner as a result of these changes.

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.”

Katy Perry shared a surprising story about how she showed her appreciation for ex-boyfriend Orlando Bloom – specifically, how she thanked him for doing the dishes while they were together.

During a September 2024 episode of her podcast, Call Her Daddy, Katy told Alex Cooper that if she walks into a spotless kitchen – dishes done, pantry doors closed, everything taken care of – she’ll be very appreciative… and ready to be intimate.

 

Chelsea 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. 

After getting a discouraging text from her ex, she felt she needed to clarify things.

Chelsea explained on The Tonight Show Starring Jimmy Fallon in October 2023 that she wanted to make it clear that wasn’t the reason for her breakup.

Look, my personal life has been pretty public lately, and some things are already out there about, well, let’s just say exploring different aspects of intimacy. I want to be clear though: the reason my relationship ended wasn’t because of any involvement with a masseuse. That’s simply not true, and I’m setting the record straight.

There are no skeletons in the America’s Got Talent judge’s closets, but there may be some slightly scandalous fashions.  

She jokingly refers to a large closet as her “sex closet.” Speaking on The Skinny Confidential Him & Her Show podcast in September 2024, she explained it’s filled with clothes and accessories. “You can have a lot of things in there—wigs, outfits, shoes, boots,” she said.

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.'”

Despite describing herself as a “very sexual person,” Shailene has shared she has some serious “beef” with porn, naming it the “junk food” of pleasure. 

In a September 2024 appearance on the She MD podcast, she explained that the way sex is typically portrayed in this country feels artificial and more like a show than genuine closeness, honesty, and connection.

It’s crucial to experience pleasure, but we often prevent each other from doing so, maybe because we don’t realize what’s truly possible. I think that’s the main problem with pornography – it offers a basic, limited experience when it could be so much more fulfilling and expansive.

After spending four years with partner Kurt Russell, Goldie revealed her biggest secret for a successful, long term relationship. 

In a September 2024 interview with TopMob News, she emphasized the importance of a satisfying sex life, explaining that it fosters connection and strengthens relationships. She believes that healthy sexual intimacy contributes to long-lasting partnerships, not just through the physical act itself, but through the emotional warmth and closeness it builds.

Ice-T revealed the secret to his and Coco Austin‘s decades-long marriage—and yes, it involves the bedroom. 

“Jungle sex,” he told TopMob News in January 2024. “That flame has to stay lit.”

He explained that when the initial spark fades and you lose that romantic connection, it’s important to deal with it right away, because acknowledging it is essential.

For Demi, there’s nothing wrong with feeling confident in the bedroom. 

In a September 2023 interview with the LadyGang podcast, she shared that she feels most confident during sex. She explained that it forces her to be fully present, quieting the thoughts and worries that usually cloud her judgment throughout the day. She clarified that this experience isn’t universal, and others may not feel the same way.

Lisa Rinna recently opened up about how aging has changed things in the bedroom with her husband, Harry Hamlin, after being married for many years.

The actress shared with Cosmopolitan in January 2024 that a man’s level of desire naturally changes over time. She explained that it’s important for women to understand this as a normal part of life and not take it personally. She believes relationships evolve to be more about companionship and accepting the natural fluctuations in sexual desire.

“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.”

Zoe and her husband Marco have created a code word to talk about sex around their kids. 

Okay, so you will NOT believe what I just found out about Marco and Zoe! Apparently, on Drew Barrymore’s show, Marco let slip they have this… thing they call ‘playing Legos naked’! And Zoe, bless her, had to explain it means, like, you know… sexy time! I’m officially obsessed with their relationship now. Seriously, ‘playing Legos naked’? That’s amazing and I need to know everything!

But the couple worried that their older twin boys were catching onto the lingo. 

Zoe remembered them asking, with disbelief, if they were kissing or planning to play with Legos without any clothes on. She said they quickly replied, ‘No, we’re not doing that!’

The singer made it one of her goals for 2024 to improve her sex life. 

That October, Billie Eilish playfully responded to a question in Vanity Fair about her love life, jokingly saying, “Yes, I’ve had a lot of good sex, so…you’re welcome!” This came amid rumors she was dating Nat Wolff.

Actress Amy Schumer revealed that hormone therapy for perimenopause and a weight-loss drug both unexpectedly boosted her sex life with her then-husband, Chris Fischer.

In a March 2025 Instagram video, she shared that she’s noticed improvements in her hair and skin, and has more energy. She also hinted at an increased libido, saying, ‘I wanna get down more, you know what I mean… I’m talking about sex.’

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2026-06-09 22:48