Madonna Reveals Jaw-Dropping Sex Confession About John F. Kennedy Jr.

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There’s only one person who has truly made Madonna feel so shiny and new. 

As a longtime fan, I was surprised to hear Madonna recently share something so personal! She’s always been incredibly private, but she revealed that her time with John F. Kennedy Jr. was when she experienced the best intimacy of her life. It’s fascinating to look back at her past relationships – everyone remembers the buzz around her with stars like Michael Jackson, Warren Beatty, and Sean Penn – but she clearly feels a special connection to that period with JFK Jr.

During a recent conversation on Grindr’s Confessions series, Madonna revealed she tends to talk about people who have passed away, starting with the example of John F. Kennedy Jr., as she shared on May 29th.

During a panel discussion, after someone mentioned John F. Kennedy Jr.—who tragically died in a 1999 plane crash with his wife, Carolyn Bessette Kennedy, and her sister Lauren Bessette—and alluded to him being attractive, Madonna playfully responded, “So you know it’s true.”

Madonna, who was rumored to have dated John F. Kennedy Jr. in the late 1980s, recently shared another surprising detail about her personal life: she enjoys listening to classical music while intimate.

Madonna described the music of Ryuichi Sakamoto, or artists similar to him, as having a captivating quality. She explained that it creates a sense of anticipation and emotion, with a dynamic rhythm that swells and releases, building intensity before ultimately resolving.

Oh my god, it’s not just Madonna who was completely changed by being with John F. Kennedy Jr.! I just read that Sarah Jessica Parker, the Carrie Bradshaw, said she hadn’t even experienced real fame until she dated him back in the early ’90s. Can you believe it? It just proves how magnetic and… transformative he was! It’s like he unlocked a whole new level of celebrity for everyone around him. I knew it! He was just… different.

I remember Sarah Jessica talking about how crazy things got when she started dating John Kennedy Jr. She told the New York Times back in ’92 that they’d go to completely secluded spots, only to see pictures of them splashed all over the tabloids the very next day. She said she hadn’t really understood what true fame meant until she met him. She described him as a lovely person, but honestly, she felt like she almost needed to apologize for even being with him – it had become so all-consuming that it really shaped who she was. She and Matthew Broderick eventually married in 1997, but she always talked about that time with John as being…intense.

I was shocked to hear Brooke Shields talk about her date with John F. Kennedy Jr.! She revealed she actually had to hold herself back from getting intimate with him, because she felt she needed to protect herself. It was their only date, and it sounds like she was really careful and aware of the situation.

She remembered deciding against a physical relationship with him, explaining she had strong feelings for him. They ended up back at his hotel, where he kissed her, and she described it as the most amazing kiss of her life.

For more stars who have been linked to Kennedys, keep reading… 

Although never officially confirmed, there were rumors that Marilyn Monroe, star of The Seven Year Itch, had romantic relationships with both John F. Kennedy and his brother, Robert F. Kennedy.

I’ll never forget when Marilyn Monroe sang “Happy Birthday, Mr. President” to JFK back in 1962. It caused such a stir, and honestly, everyone immediately started talking about whether they were having an affair. It was all anyone could think about at the time!

Shirley MacLaine, who attended the birthday party, claimed she saw what appeared to be developing romantic relationships between both Kennedy brothers and other people.

In her 2024 memoir, The Wall of Life: Pictures and Stories from this Marvellous Lifetime, Shirley recalled witnessing a moment at the after-party: Jack Kennedy had just left the bedroom as Bobby Kennedy entered, and Marilyn Monroe was inside.

In 2012, James Spada, the author of Monroe: Her Life in Pictures, told People magazine that it seemed Marilyn Monroe had intimate relationships with both John F. Kennedy and Robert Kennedy.

Actress Cheryl Hines met her future husband, Robert F. Kennedy Jr., through a connection made by her Curb Your Enthusiasm co-star, Larry David. They were introduced during a ski trip in 2006.

Cheryl and Robert didn’t begin dating until 2011, but Cheryl has said that the creator of Seinfeld never tried to set them up. He actually warned her not to get involved with the Kennedy family.

She told the New York Times in 2023 that part of what makes Larry endearing is his predictable response. No matter what you say to him, he always asks, ‘Why would you do that? Are you crazy?’

Although her marriage often received attention during her husband RFK Jr.’s run for president in 2024 and his later position as U.S. Secretary of Health and Human Services under President Trump, she has emphasized that her family’s privacy is most important to her.

She described Bobby as both intelligent and humorous, noting that his playful side isn’t always obvious to others. She also appreciated his adventurous spirit, which she felt would encourage her to try new things, and she generally enjoyed that challenge.

Despite their divorce, the relationship between Maria Shriver and Arnold Schwarzenegger remains one of the most memorable romances in their family’s history. They married in a traditional Catholic ceremony on April 26, 1985, almost ten years after they first met, and the wedding was held near the famous Kennedy family estate in Hyannis Port, Massachusetts.

Arnold Schwarzenegger and his wife had four children: Katherine, born in 1989; Christina, born in 1991; Patrick, born in 1993; and Christopher, born in 1997.

Maria and Arnold were together for eight years, during which he served two terms as Governor of California from 2003 to 2011. They separated later in 2011.

Even after their split, Arnold—who is also father to Joseph Baena (born in 1997 to his former housekeeper, Mildred Patricia Baena)—has stated that he and his ex-partner have stayed “really good friends and very close.”

Despite going through a divorce, Arnold Schwarzenegger and Maria Shriver continued to celebrate holidays and birthdays together as a family. In a 2023 interview with The Hollywood Reporter, Schwarzenegger said they should receive an award for minimizing the impact of their split on their children.

Although she wasn’t officially romantically involved with anyone from the Kennedy family, the actress known for Blue Lagoon remembered spending time with John F. Kennedy Jr. before he began dating Carolyn Bessette.

Brooke shared on the Howard Stern show in 2022 that she once went out with a man who repeatedly told her she resembled his mother, which she found odd.

Brooke acknowledged the comparison to Jacqueline Kennedy Onassis was flattering, but also admitted she was unsure how to react to it.

She wasn’t sure what to think of the man, either. Despite going on what she called a ‘real date,’ it didn’t develop into a relationship.

She remembered thinking she cared for him too deeply to have a casual encounter. They ended up back at the hotel where he was staying, and he kissed her. She described it as the most amazing kiss of her life.

Brooke explained why she didn’t pursue the situation further: she was afraid of ruining a budding romance. She thought, ‘If you sleep with him, he might stop talking to you, and you wouldn’t be able to cope with that.’

A friend of John F. Kennedy Jr. says he and Madonna had a short-lived romance in the late 1980s. At the time, Madonna was still legally married to Sean Penn.

According to a source interviewed for the biography JFK Jr.: An Intimate Biography, Madonna was just a brief, casual relationship – and not even a significant one at that.

Rosemarie Terenzio, who used to work for John F. Kennedy Jr., claims that he asked her to appear on the cover of his magazine, George, years after they had a brief romantic relationship. The idea was to playfully imitate a famous image of his mother, Jacqueline Kennedy Onassis.

Terenzio noted that Madonna declined via fax. 

Terenzio remembered receiving a note from someone who jokingly asked him to be their mother. He recalled the note saying, ‘Thanks for asking me to be your mother, but I’m afraid I could never do her justice – my eyebrows aren’t thick enough!’

Kristin Davis, known from Sex and the City, revealed she dated John F. Kennedy Jr. for a short time between 1991 and 1992. She ended things because she felt he was too accustomed to living his life in the public eye.

In a 1992 interview with the New York Times, she explained that she didn’t understand true celebrity until she met John. She described him as a kind person, but confessed she felt embarrassed about their relationship, saying it had become the most significant aspect of her public identity.

Sarah Jessica Parker, who later had three children with her husband Matthew Broderick, playfully dismissed public interest in her brief romance with John F. Kennedy Jr., calling it “pathetic.” She joked that her obituary would focus on that relationship, saying, ‘They are going to say, ‘Oh, yeah, Sarah once dated John Kennedy.’’

In 2017, Sarah Jessica Parker revisited her brief romance with John F. Kennedy Jr., describing their kisses as enjoyable but explaining she felt a responsibility to safeguard his public image.

She described his hair as beautiful and striking, comparing it to a paintbrush. During an interview on Watch What Happens Live, she also shared that she’d be more willing to talk about him if she believed he was living a full and happy life and achieving his potential.

 

Uma Thurman, known for her role in Kill Bill, famously dated John F. Kennedy Jr. in the early 1990s, before he began a relationship and eventually married Carolyn Bessette-Kennedy.

Despite the show’s frustrating depiction of her, Daryl spoke up to share her side of the story while the series was still being broadcast in 2026.

In an opinion piece for the New York Times, she stated that the character based on her in the series doesn’t reflect her life, how she acts, or her relationship with John. She emphasized that the character’s actions and behavior are simply not true.

Meanwhile, JFK Jr.’s cousin Douglas Kennedy concurred. 

Douglas said that Daryl was always kind and genuinely cared about John. He believes the way she’s portrayed on the show isn’t accurate, telling Page Six it’s a misrepresentation of her true character.

In 2018, after months of speculation about a relationship, Chris Pratt and Katherine Schwarzenegger confirmed they were dating when Chris posted a heartfelt birthday message for her on Instagram.

In a December post, Chris wished their “Chief” a happy birthday, sharing how much they appreciate them. Chris wrote that the Chief’s smile is infectious and that they deeply value their relationship, feeling blessed to have them in their life. They expressed gratitude for all the happy moments they’ve shared – the laughter, affection, conversations, adventures, and loving support.

The couple, who met at church, got married in June 2019. They had their first daughter, Lyla, fourteen months later. Their family grew with the arrival of Eloise in 2022, and their son, Ford, in 2024.

Chris, who shares son Jack (born in 2012) with his ex-wife Anna Faris, revealed he was going through a difficult time before he met Katherine. He explained that she quickly helped him feel better and recover emotionally.

You know, I’ve always believed in timing, and I love how Drew Barrymore’s guest put it recently: sometimes, when it’s truly meant to be, things just happen quickly. It’s like life has a fast-forward button! You meet someone, there’s an instant connection, and suddenly you’re falling in love and planning a wedding. It’s beautiful when it unfolds that way – a real ‘boom’ moment!

And you live happily ever after. 

Katherine told People in March 2026 that her husband always has a great sense of humor and keeps things light, even when he’s not feeling well. She explained that he’s always cracking jokes, which helps to brighten even difficult times.

Soon after his divorce from Jennifer Lopez in 2024, rumors began circulating that Ben Affleck was dating Kathleen “Kick” Kennedy, the daughter of Robert F. Kennedy Jr. and Emily Ruth Black.

According to a source familiar with the matter, the two individuals were not in a romantic relationship. The source stated they barely knew each other.

A surprising rumor spread online in 2024 claiming that Selena Gomez, who would later marry Benny Blanco in 2025, had briefly dated Jack Schlossberg – the son of Caroline Kennedy and Ed Schlossberg – between 2020 and 2021. The story alleged that Jack had playfully suggested Selena could one day live in the White House, and that she was charmed by the idea.

John F. Kennedy’s grandson definitely seemed impressed with Selena Gomez. He shared a post on his Instagram Story in October 2020 about her “When We All Vote” merchandise collaboration with Dover Street Market, writing, “I need this, no matter the price!”

Selena quickly denied the rumors about a relationship, responding to a post claiming they were together with a simple, “Never met this person. Sorry.”

Oh my god, you will NOT believe this! So, during Kim’s Vogue shoot in 2019, someone on set mentioned that Caroline and Ed’s son, Jack, had a crush on Kendall! And Kim’s reaction? It was the cutest! Her eyes literally lit up – the writer said she totally started thinking about how she and Caroline could maybe, possibly, help things along with some matchmaking! Like, imagine the power couple possibilities! I swear, she lives for this stuff, and it’s amazing!

Kim revealed she recently bought Jackie Kennedy’s watch at auction for over $300,000.

She recounted wearing the watch during a visit to the White House, saying it made her feel empowered and ready to accomplish her goals. However, she later explained that she’d returned the watch to Cartier after receiving a warning. On a January 2026 episode of her show, ‘Khloe in Wonder Land,’ she claimed someone told her she couldn’t keep it, believing the watch was cursed.

Before Miley Cyrus began dating Maxx Morando, she was in a relationship with a star from the show The White Lotus between 2014 and 2015. Interestingly, Patrick Schwarzenegger refers to Eunice Kennedy as his grandmother.

Despite only dating briefly, the couple was seen out together several times, including Miley attending a football game with her then-boyfriend who was a student at USC.

By January 2016, Miley Cyrus and Liam Hemsworth were back together, and Patrick Schwarzenegger had started dating Abby Champion, who is now his wife.

Even long after they broke up, Patrick’s father, Arnold, often said that Miley had made a very positive impact on their family.

Arnold described the “Flowers” singer as a remarkably talented and wonderful person, also noting she was a delightful houseguest during a family ski trip, as he shared on Watch What Happens Live in June 2025.

Patrick and Miley are still friends and even shared a heartwarming moment at the 2026 Golden Globes.

Before dating Travis Kelce of the Kansas City Chiefs, Taylor Swift briefly dated Conor Kennedy from the Kennedy family in the summer of 2012.

When asked to describe the musician, his grandmother, Ethel Kennedy, called him “spectacular” in a conversation with Cape Cast.

Ethel described her as wonderful, both personally and outwardly. She emphasized her kindness, adding that she was always up for anything and willing to try new things.

Taylor met Ethel Kennedy before she started dating Conor Kennedy. They first connected at the Sundance Film Festival in January 2012, at the premiere of Ethel’s documentary. Later that summer, Taylor visited Hyannis Port, where she and Conor began a relationship, and Ethel immediately liked her.

Ethel remembered that she’d always jumped right in and tried anything new. She’d never sailed, so she sailed. Never gone drag racing? She tried that too. She picked up whatever everyone else was doing, and surprisingly, she was naturally good at it – no complaints, no hesitation.

Not everyone in the Kennedy family was happy with the fast-moving relationship. Vicki Kennedy claimed that Taylor and Conor unexpectedly showed up at their daughter Kyle Francis Kennedy’s wedding in August.

For Taylor’s part, she thought the whole thing was a big “misunderstanding.”

Honestly, I’m someone who always makes sure I’m welcome before attending anything – it’s just my nature. And the thought of ever overshadowing someone else? That’s something I’d absolutely avoid. I truly believe in respecting the moment and those around me.

Their relationship didn’t last, and they broke up in October 2012. Later, in 2024, Conor proposed to Giulia Be.

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2026-05-29 16:19