Taylor Swift, Brooke Shields & More Stars Who Dated Kennedys

Marilyn Monroe

Rumors of The Seven Year Itch star romancing several Kennedys were never confirmed. But reports linked her to both former president John F. Kennedy and his brother Robert F. Kennedy. 

After she infamously sang “Happy birthday Mr. President” for JFK in 1962, there was public speculation of an affair. 

Meanwhile, Shirley MacLaine, who was present at that birthday celebration, alleged she witnessed possible affairs brewing with both Kennedy men. 

“Jack Kennedy had just walked out of the bedroom behind me,” Shirley wrote in her 2024 memoir The Wall of Life: Pictures and Stories from this Marvellous Lifetime of what she saw at the fête’s after-party, “and Bobby [Robert] Kennedy had just walked in. Marilyn was in the bedroom.”

James Spada, author of Monroe: Her Life in Pictures also told People in 2012, “It was pretty clear that Marilyn had had sexual relations with both Bobby and Jack.”

Cheryl Hines

The Curb Your Enthusiasm actress was introduced to now real-life husband Robert F. Kennedy Jr. by her on-screen husband Larry David during a 2006 ski trip. 

Cheryl and Robert didn’t start dating until years later in 2011, but Cheryl admitted that the Seinfeld creator never intended to play match-maker. In fact, he advised her against joining the Kennedy family. 

“It's part of the fun of Larry," she told the New York Times in 2023. "You just know no matter what you say to him, he's going to say, 'Why would you do that? Are you crazy?’”

And while their marriage took center stage during RFK Jr.’s 2024 presidential campaign, and subsequent role as the United States Secretary of Health and Human Services under President Donald Trump’s administration, she has said that their private life is what she prioritizes. 

“Bobby is very smart and funny, although a lot of people don’t see the funny side,” she added. “He also has this sense of adventure that will catapult me outside of my comfort zone, which I find exciting most of the time.” 

Arnold Schwarzenegger

While they are no longer together, Maria Shriver and Arnold Schwarzenegger’s romance is among the family’s most iconic love stories. Nearly a decade after the couple met, they wed in an April 26, 1985 traditional Catholic ceremony near the famed Kennedy compound in Hyannis Port, Mass.  

The Terminator star and his journalist bride went on to welcome Katherine Schwarzenegger in 1989, Christina Schwarzenegger in 1991, Patrick Schwarzenegger in 1993 and Christopher Schwarzenegger in 1997. 

Maria supported Arnold through two terms as the Governor of California between 2003 and 2011, before the couple split later that same year. 

Despite their separation, Arnold—also dad to Joseph Baena, born in 1997, with the family’s former housekeeper Mildred Patricia Baena—emphasized they have remained “really good friends and very close.”

“Even though we had this drama, we did Easter together, Mother’s Day together, the Christmases together, all birthdays—everything together,” Arnold told The Hollywood Reporter in 2023. “If there’s Oscars for how to handle divorce, Maria and I should get it for having the least amount of impact on the kids.”

Brooke Shields 

While she never officially dated a Kennedy, the Blue Lagoon star reminisced on going out with JFK Jr. prior to his relationship with Carolyn Bessette. 

“We went out,” Brooke recalled during a 2022 appearance on Howard Stern. “I was invited with the family. He kept saying I looked like his mother which was really interesting.”

Indeed, while Brooke considered the Jacqueline Kennedy Onassis comparison “a compliment,” she admitted, “It was also like, ‘I don’t know how to feel about this.’”

Nor did she know how to feel about the man himself. Though she said they had a “real date,” it didn’t lead to anything serious. 

“I wouldn’t sleep with him because I kind of loved him too much,” she recalled. “We went back to this chalet hotel he was in. He kissed me and it was the best kiss I’d ever had in my life.”

As for why they didn’t take it further?  “It was so precious to me,” Brooke explained. “I was like, ‘Oh my god you’re falling in love and if you sleep with him, he may not talk to you again and you can’t handle that.’”

Madonna

According to a friend of JFK Jr., the “Material Girl” singer and George magazine founder had a brief romance in the late 1980s, while she was still technically married to Sean Penn. 

“Madonna was totally a fling,” the unnamed associate said in an interview for JFK Jr.: An Intimate Biography. “Nothing more. Barely a fling at that.”

JFK Jr.’s former assistant Rosemarie Terenzio alleged that years after their dalliance, he had asked her to pose for a cover of George, spoofing his mom Jacqueline Kennedy Onassis.

Terenzio noted that Madonna declined via fax. 

“Dear Johnny boy, Thanks for asking me to be your mother, but I’m afraid, I could never do her justice,” Terenzio recalled of the note. “My eyebrows aren’t thick enough for one.”

Sarah Jessica Parker

According to the Sex and the City alum, she and JFK Jr. went on a few dates between 1991 and 1992, but she ultimately called it off when she found him to be too much of “a public domain kind of a guy.”

“I never had any idea what real fame was until I met John,” she told the New York Times in 1992. “ He's a nice man, but for God's sake, I feel like I should apologize for dating him. It has become the defining factor in the person I am.”

Given how casual their romance was, Sarah Jessica—who went on to welcome three children with now-husband Matthew Broderick—joked that she found the public’s fascination with it “pathetic,” adding, “When I die, they are going to say, 'Oh, yeah, Sarah once dated John Kennedy.’"

Years later, Sarah Jessica reflected on their romance again in 2017, admitting it was “pleasant” to share a kiss or two with JFK Jr., but noted that she wanted to protect his legacy. 

“He had exquisite hair, it was like a paintbrush,” she recalled during an appearance on Watch What Happens Live. “If he were accomplishing all the things that I’m certain he was going to accomplish and living a really joyful adventurous life then I would probably feel more comfortable answering more questions about him.”

Daryl Hannah

As depicted in FX's Love Story, the Kill Bill actress had a high profile romance with JFK Jr. in the early 1990s, leading up to his romance and eventual marriage with Carolyn.

But while the Ryan Murphy series portrays an irritating version of Daryl, she spoke out to reclaim her truth amid the series airing in 2026. 

"The character 'Daryl Hannah' portrayed in the series is not even a remotely accurate representation of my life, my conduct or my relationship with John," she wrote in an op-ed for the New York Times. "The actions and behaviors attributed to me are untrue."

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

"Whenever I saw her, she was very sweet and had [John's] best interests at heart," Douglas told Page Six of Daryl, adding of the show's interpretation of her, "I think that's a misrepresentation."

Chris Pratt

Months after the Guardians of the Galaxy star sparked romance rumors with Katherine Schwarzenegger in 2018, the duo went Instagram official when Chris shared a sweet birthday tribute.  

“Happy Birthday Chief!” Chris wrote in a post that December. “Your smile lights up the room. I’ve cherished our time together. Thrilled God put you in my life. Thankful for the laughs, kisses, talks, hikes, love and care.”

Following a short engagement, the couple—who met in church—tied the knot in June 2019. They welcomed daughter Lyla 14 months later. Her little sister Eloise joined the fam in 2022 and brother Ford came along in 2024.

Admitting he was “broken” before they met, Chris—who also shares son Jack, born in 2012, with ex Anna Faris—emphasized just how quickly Katherine healed him. 

“God has a fast-forward button, you know,” he put it during a 2023 appearance on The Drew Barrymore show. “When it's right—boom!—you're hit. You fall in love, you get married.”

And you live happily ever after. 

"I would say that he's definitely always really humor-filled,” Katherine explained to People in March 2026, praising her husband for keeping life light. “Even when he's sick, he's making jokes that make a rough situation or a rough week have some lighthearted moments.”

Ben Affleck

Shortly after he and Jennifer Lopez filed for divorce in 2024, the Good Will Hunting alum was rumored to be dating Kathleen “Kick” Kennedy, the daughter of Robert F. Kennedy Jr. and Emily Ruth Black. 

However, a source with knowledge of the situation told E! News at the time that they were “not romantically involved,” adding, “They only know each other in passing.”

Selena Gomez

In 2024, a retrospective rumor that Selena Gomez—who tied the knot with Benny Blanco in 2025—had dated Caroline Kennedy and Ed Schlossberg’s son Jack Schlossberg between 2020 and 2021 went viral. The rumor claimed that Jack had “promised” Selena the White House, and that she “fell for it.” 

And JFK's grandson certainly showed her some interest. Posting about Selena’s “When We All Vote” merch collaboration with Dover Street Market in October 2020, he wrote on his Instagram Story, “Whatever it costs! I have to have it!” 

However, Selena quickly shot down rumors he had much more. Commenting on the Instagram post that detailed their alleged romance, she wrote, “Never met this human. Sorry.”

Kendall Jenner

During Kim Kardashian’s 2019 photo shoot with Vogue, a member of the crew told her Caroline and Ed's son Jack had a crush on sister Kendall which, the writer detailed of the piece, caused the SKIMS founder’s eyes to “twinkle at the prospect of colluding over some dynastic matchmaking.”

In fact, Kim went on to share that she had recently purchased Jackie O’s watch at an auction for more than $300,000. 

“I wore it when I went to the White House,” she said. “It gave me some power: Let’s get in there and get this done!” Though she later revealed she’d given the watch to Cartier, claiming during a January 2026 episode of Khloe in Wonder Land that “someone called me and was like, ‘You cannot accept that watch,’” insisting the timepiece was “cursed.”

Miley Cyrus

Well before fiance Maxx Morando was buying Miley Cyrus flowers, she dated the White Lotus star between 2014 and 2015. (As Arnold and Maria’s son, Patrick calls Eunice Kennedy Grandma.) 

Although the former couple only dated for a few short months, they made several public appearances together, with Miley even attending a football game with the then-USC student.  

By January 2016, though, Miley had reunited with Liam Hemsworth, while Patrick had met now-wife Abby Champion. 

Years after their split, Patrick’s dad Arnold emphasized that Miley made a great impression on their family. 

“She is a wonderful, wonderful girl and human being and very, very talented,” Arnold said during a June 2025 episode of Watch What Happens Live, adding that the “Flowers” singer was “just such a wonderful houseguest” during a family ski trip. 

YPatrick and Miley remain on friendly terms, too, even sharing a sweet moment together at the Golden Globes in 2026.

Taylor Swift

Before she found her guy on the Chiefs, Travis Kelce, Taylor huddled up with the Kennedy family when she briefly romanced Conor Kennedy in the summer of 2012. 

At the time his grandmother Ethel Kennedy filled in the blank space by calling the musician “spectacular” in a chat with Cape Cast. 

“She is just sensational inside and out,” Ethel added. “She’s very kind. You know what she really is? She’s game.”

Indeed, while Taylor dated Conor, she met Ethel first; attending the January 2012 premiere of her documentary at the Sundance Film Festival. That summer, she visited Hyannis Port where sparks flew with Conor. And Ethel knew she was fantastic when she walked in.

“She had never sailed before—she sailed,” Ethel recalled. “She had never gone dragging before—she dragged. She played anything that everyone else was doing, and she was good at it. No fuss.”

However, not every Kennedy was so thrilled about the whirlwind romance, with Vicki Kennedy alleging that Taylor and Conor had crashed daughter Kyle Francis Kennedy’s August wedding that summer.

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

“I would never knowingly show up somewhere that I thought I wasn’t invited to,” she assured to Rolling Stone at the time. “And I would never want to upstage anybody.”

Ultimately, it wasn't forever and always between the pair as they split by summer's end in October 2012. Conor went on to propose to Giulia Be in 2024.