Taylor Swift, Brooke Shields & More Stars Who Dated Kennedys

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John F. Kennedy Jr. and Carolyn Bessette aren’t the only Kennedy couple to make headlines. 

Before he became known for his fashion sense and public image, John F. Kennedy was already linked to several famous women. In an episode of the FX series Love Story: John F. Kennedy & Carolyn Bessette, Carolyn (played by Sarah Pidgeon) playfully lists some of John’s rumored past relationships – including Daryl Hannah, Sarah Jessica Parker, Madonna, and Brooke Shields – while they’re relaxing at home (with John played by Paul Anthony Kelly).

Still, “I never dated Brooke Shields,” JFK Jr. insisted. “I kissed her once and her mom was there.”

The story seems to come directly from the actress who starred in Blue Lagoon, as she shared a comparable experience a few years ago.

She remembered going out with her family and, during a 2022 interview with Howard Stern, shared a funny story. Someone kept telling her she resembled his mother, which she found both flattering and a little strange. She said it made her feel unsure how to react.

The story that their kiss happened while their mothers, Jacqueline Kennedy Onassis and Teri Shields, were watching seems to be an exaggeration. According to Brooke, JFK Jr. actually asked her to leave with him, and they ended up alone in a hotel room.

She explained she hadn’t wanted to sleep with him because her feelings were too strong – she was deeply in love with him. She remembered his kiss being incredible, the best she’d ever experienced, and she was completely captivated by his looks and personality.

The series touches on John F. Kennedy Jr.’s relationship with Daryl Hannah, though Hannah recently wrote in The New York Times that it wasn’t portrayed accurately. Before dating Hannah, Kennedy was linked to Madonna in the late 1980s.

John definitely dated the Sex and the City star in the early 1990s, but Sarah Jessica Parker later referred to their brief relationship as “The Kennedy fiasco,” highlighting the intense media attention surrounding the Kennedy heir.

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She told the New York Times in 1992 that they’d often escape to secluded places, only to see photos of themselves splashed across the tabloids the next day. She explained that she didn’t truly understand fame until she met John, describing him as a kind person but admitting she sometimes felt she needed to apologize for their relationship. She felt it had become the most significant aspect of her identity.

Sarah Jessica Parker, who has been married to Matthew Broderick for almost 30 years and has three children with him, actually anticipated the attention her brief romance would receive. She joked, ‘It’s ridiculous. When I’m gone, people will remember me as the woman who briefly dated John Kennedy.’

Years later, Taylor Swift experienced similar intense media attention when she briefly dated Conor Kennedy, a relative of JFK Jr., in the summer of 2012. Their short-lived romance made headlines, particularly after they were seen at a Kennedy family wedding that August.

Vicki Kennedy, Kyle Kennedy’s mother, said they texted her just an hour before the wedding asking if they could attend. She told the Boston Herald that she specifically asked them not to come, but they showed up anyway.

Months later, Taylor shared that the whole thing was born out of “the biggest misunderstanding.”

Taylor Swift told Rolling Stone in a 2012 interview, after her breakup with Conor Kennedy, that she would never intentionally go to a place where she wasn’t welcome, and she’d never want to draw attention away from someone else.

It’s become common for people connected to the Kennedy family to publicly correct inaccurate stories. For example, when rumors surfaced in 2024 that Selena Gomez had been dating Jack Schlossberg for a year (between 2020 and 2021), Gomez quickly responded to a comment on Instagram, stating, “Never met this human sorry.”

As a longtime follower of celebrity connections, I’ve always been fascinated by those linked to the Kennedy family! It’s amazing to see how many stars have dated or been romantically involved with someone from that famous family. I’ve put together a list of all the celebrities who might have a Kennedy connection – it’s quite a roster!

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

Following her famous performance of “Happy Birthday, Mr. President” for John F. Kennedy in 1962, rumors began circulating about a possible romantic relationship between them.

As a lifestyle observer, I’ve always been fascinated by the stories surrounding the Kennedys. At a birthday party I attended around that time, I actually witnessed what seemed like some definite chemistry between Shirley MacLaine and both John and Robert Kennedy. It definitely led to speculation, even back then, about possible connections.

In her 2024 memoir, The Wall of Life: Pictures and Stories from this Marvellous Lifetime, Shirley described how she saw Jack Kennedy leave the bedroom just as Bobby Kennedy entered. Marilyn Monroe was inside the bedroom at the time, according to Shirley’s account of the fête’s after-party.

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

Cheryl Hines, known for her role in Curb Your Enthusiasm, met her future husband, Robert F. Kennedy Jr., thanks to a setup by her 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 against getting involved with the Kennedy family.

She explained to the New York Times in 2023 that a humorous part of Larry’s personality is his predictable response to anything: he always asks, ‘Why would you do that? Are you crazy?’

Although their marriage was often in the spotlight during RFK Jr.’s run for president in 2024 and her later position as U.S. Secretary of Health and Human Services under President Trump, she has emphasized that her personal life is her main focus.

She described Bobby as both intelligent and humorous, noting that not everyone appreciates his sense of humor. She also mentioned his adventurous spirit would push her to try new things, which she generally enjoyed.

Even though Maria Shriver and Arnold Schwarzenegger are divorced, their relationship 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, 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 as Governor of California from 2003 to 2011. They separated later in 2011.

You know, even though my marriage ended, I’ve stayed incredibly close with my ex-wife – we’re really good friends. And, of course, I’m also a dad to Joseph Baena, born in 1997. He’s a wonderful part of my life, and his mother is Mildred Patricia Baena.

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 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 attended an event 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 confessed she was unsure how to react to it.

She wasn’t sure what to make of the man, either. While they went on what she called a proper date, it didn’t turn into a relationship.

She remembered not wanting to sleep with him, explaining it was because she had strong feelings for him. They went back to his hotel, and he kissed her – she said it was the most amazing kiss of her life.

Brooke explained why she didn’t pursue the situation, saying, “It meant so much to me. I thought, ‘Oh my gosh, you’re falling for him, and if you sleep with him, he might stop talking to you, and you couldn’t deal 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 book JFK Jr.: An Intimate Biography, Madonna was just a brief, casual relationship. The source described it as “barely a fling.”

Rosemarie Terenzio, who used to work for John F. Kennedy Jr., claims that he jokingly suggested years after their brief relationship that she appear on the cover of his magazine, George, as a playful imitation 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 lived too much of 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 part of her public identity.

Sarah Jessica Parker, who later had three children with her husband Matthew Broderick, playfully dismissed the public’s intense interest in her past relationship, calling it “pathetic.” She joked that even after she’s gone, people will remember her primarily for having 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 flowing, comparing it to a paintbrush. She also explained that she’d be more willing to talk about him if she believed he was living a full and happy life and achieving his goals, as she always expected he would.

 

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

Although the Ryan Murphy series depicted Daryl in a frustrating way, she publicly shared her side of the story while the show was still airing in 2026.

In an opinion piece for the New York Times, she stated that the portrayal of ‘Daryl Hannah’ in the series was completely inaccurate, and didn’t reflect her life, how she acted, or her relationship with John. She emphasized that the character’s actions and behavior were fabricated.

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

You know, whenever I interacted with Daryl, she was genuinely kind and always seemed to want what was best for John. Honestly, watching the show’s portrayal of her, I really feel it doesn’t capture who she truly was – it’s a bit of a misrepresentation, in my opinion.

In 2018, after months of speculation about a romance, Chris Pratt and Katherine Schwarzenegger confirmed their relationship 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 their smile brightens any space, and they feel lucky to have them in their life, treasuring all the joyful moments, affection, and support they’ve shared – from laughter and kisses to meaningful conversations and outdoor adventures.

The couple, who met at church, got married in June 2019. They had their first daughter, Lyla, 14 months later. Their family grew with the arrival of Eloise in 2022, and then their son, Ford, in 2024.

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

I absolutely love how he described finding love! He said on Drew Barrymore’s show that sometimes, when the time is right, things just happen quickly – like God presses fast-forward. You meet someone, you fall head over heels, and suddenly you’re getting married! It’s such a beautiful way to think about it.

And you live happily ever after. 

Katherine told People magazine in March 2026 that her husband is consistently funny and keeps things lighthearted. She explained that even when he’s feeling unwell, he manages to crack jokes and bring some cheer to difficult times.

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

According to a source familiar with the situation, the individuals were not romantically involved at the time, and only knew each other casually.

A surprising rumor gained popularity 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 interested in Selena Gomez. He publicly expressed his enthusiasm on Instagram in October 2020, posting about her “When We All Vote” merchandise collaboration with Dover Street Market and writing, “Whatever it costs! I have to have it!”

Selena quickly denied the rumors about a romantic connection. She responded to an Instagram post claiming they were dating, stating, “I’ve never met this person. Sorry.”

During a 2019 photoshoot with Vogue, someone on set mentioned that Caroline and Ed’s son, Jack, had a crush on Kendall Jenner. According to the writer, Kim Kardashian reacted with amusement at the idea of potentially arranging a relationship between them, and her eyes ‘twinkled’ at the thought.

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

She recalled wearing the watch during a visit to the White House, saying it made her feel empowered and determined to succeed. However, she later explained that she’d returned the watch to Cartier after receiving a warning – during a 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 started dating Maxx Morando, she was with the star of The White Lotus from 2014 to 2015. Interestingly, Patrick Schwarzenegger refers to Eunice Kennedy as his grandmother.

Despite only dating briefly, the former 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 had gotten back together with Liam Hemsworth, and Patrick Schwarzenegger had started dating Abby Champion, who would later become his wife.

Even long after they broke up, Patrick’s dad, Arnold, often said that Miley had made a really 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 Travis Kelce stole her heart on the Chiefs, I remember Taylor briefly dating Conor Kennedy way back in the summer of 2012. It feels like ages ago, but as a fan, I definitely remember the buzz!

When asked to describe the musician, his grandmother, Ethel Kennedy, called him “spectacular” during 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 dated Conor Kennedy. They first connected at the Sundance Film Festival in January 2012, where Ethel attended the premiere of Taylor’s documentary. Later that summer, Taylor visited Hyannis Port and began dating Conor, and Ethel immediately thought Taylor was wonderful when they met.

Ethel remembered that she’d always jumped right in and tried everything. “I’d never sailed before, but I gave it a go,” she said. “Never been water skiing? I tried that too. I just joined in whatever everyone else was doing, and surprisingly, I was pretty good at it—no complaints, no problems.”

Not everyone in the Kennedy family was happy about 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.”

She told Rolling Stone she would never intentionally go to an event if she didn’t believe she’d been invited, and she’d never want to draw attention away from others.

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

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2026-03-13 00:19