Every Kennedy Family Member Who Has Dated a Celebrity

From Conor Kennedy's relationship with Taylor Swift to JFK Jr.'s fling with Madonna, here's a look back at the celebrities who have dated the famous family

The Kennedys were the first political family to be celebrities in their own right, so it's no surprise that, through the years, they've paired off with some of Hollywood's brightest stars.

Over the years, various members of the Kennedy family have been romantically linked to A-listers dating back to John F. Kennedy's rumored romance with Marilyn Monroe. This week, as rumors swirl (which some dispute) that Ben Affleck has been seeing Kick Kennedy, look back at all the Kennedys who have dated — or even married! — actors and singers.

John F. Kennedy Jr.

Before he and Carolyn Bessette-Kennedy tied the knot in 1996, John F. Kennedy and Jacqueline Kennedy Onassis' only son, John F. Kennedy, Jr., was one of the most eligible bachelors in New York — and beyond! During this time, he dated various high profile women including Daryl Hannah, and had a fling with Madonna in the late 1980s. (It's a string of A-list romances that helped him earn the title of PEOPLE's Sexiest Man Alive in 1988.)

JFK Jr. and Bessette were married for nearly three years before the tragic plane crash that killed the couple along with her sister, Lauren Bessette.

Conor Kennedy

Conor Kennedy, whose parents are Robert F. Kennedy Jr. and the late Mary Richardson Kennedy, dated Taylor Swift in 2012.

At the time, Conor's grandmother, Ethel Kennedy, said that Swift is "sensational inside and out.” And though Swift spent a good deal of time around the Kennedy compound that summer (so much so that she bought a place nearby, which she later sold), by the time Conor left to go back to school, things had fizzled out.

In August 2024, Conor announced in a joint Instagram post that he and Giulia Be were engaged.

“easiest yes of all time ????,” the singer and actress, whose real name is Giulia Bourguignon Marinho, wrote in the caption alongside photos and video from their special moment.

Maria Shriver

Maria Shriver, whose parents are Eunice Kennedy Shriver and Robert Sargent Shriver Jr., was married to actor, body builder and former Governor of California Arnold Schwarzenegger for 25 years after first meeting in 1977. They wed in 1986 in Hyannis, Massachusetts — celebrating at the Kennedy compound — with Shriver's cousin, Caroline Kennedy, as her maid of honor.

After welcoming four children together, Shriver and Schwarzenegger split in 2011, officially settling their divorce 10 years later.

Patrick Schwarzenegger

Shriver and Schwarzenegger's eldest son, Patrick, dated Miley Cyrus from November 2014 to April 2015.

After first being spotted together at a Halloween event in L.A., a few weeks later the two were seen kissing at a University of Southern California football game where Patrick was a student.

When the news of their split came in April 2015, a source told PEOPLE, "They're just in two different places in their lives. He's in college and she's focused on her music and career."

In December 2023, Patrick announced his engagement to model Abby Champion.

Katherine Schwarzenegger

Shriver and Arnold's eldest daughter, Katherine Schwarzenegger, married actor Chris Pratt in June 2019 after announcing their engagement in January of that year. In August 2020, the couple welcomed their first child together, daughter Lyla, before expanding their brood in 2022 with daughter Eloise and in June 2024 shared they're expecting a third child.

Pratt is also dad to son Jack who he shares with ex Anna Faris.

Robert F. Kennedy Jr.

Robert F. Kennedy Jr. wed Curb Your Enthusiasm actress Cheryl Hines in 2014.

The couple has seven children between them as Hines shares her daughter, Catherine, with ex Paul Young and Kennedy has six children — sons Bobby III, Conor, Finn and Aidan and daughters Kick and Kyra — from his two previous marriages.

John F. Kennedy

Following a particularly sultry performance of "Happy Birthday" to then President John F. Kennedy, speculation flew about the nature of the relationship between Marilyn Monroe and the 35th president.

"She was enamored of him," Tony Oppedisano, Frank Sinatra's friend and author of  Sinatra and Me: In The Wee Small Hours told PEOPLE of the two, sharing that they were "obviously" intimate.

Though he added, "She wasn't about to break up [the president's] marriage, so she wouldn't let it go that far, even if she felt that deeply."

There was also reportedly a fling with the president's younger brother,  Robert F. Kennedy, after things "phased out" with JFK.

"I don't think it lasted anywhere near as long or was as deep as it was with JFK. Bobby was a different mentality all together," Oppedisano explained.

Patricia Kennedy Lawford

John F. Kennedy's sister, the sixth child of Joseph and Rose Kennedy, was working in the entertainment industry in Los Angeles in the 1940s when John introduced her to the English actor Peter Lawford, according to her bio on the JFK Presidential Library and Museum website. They wed in 1954 and had four children before divorcing in 1965.

Joseph P. Kennedy

The patriarch of the Kennedy clan, Joseph P. Kennedy, Sr., was a powerful political figure and influence over his nine children with wife Rose. And that included setting a precedent for extramarital dalliances with Hollywood starlets.

Kennedy was known to have had long-term affairs with Old Hollywood icons Marlene Dietrich and Gloria Swanson, about which both women spoke in their later years.

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