It’s no secret that Taylor Swift has a deep admiration for the Kennedy family. She’s even dated someone in the famous American dynasty, but how did they really feel about the world’s biggest popstar being associated with their family?
In 2012, Taylor Swift started dating Conor Kennedy, the grandson of Robert F. Kennedy and son of RFK Jr., when she was 22, and he was 18. She has met quite a chunk of the Kennedy family, sans people who were directly in John F. Kennedy’s lineage.
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During her relationship with Connor, she met his grandmother, Ethel Kennedy, and wrote a song about her marriage with RFK. “It was such a fun moment when she was just in love with the song,” the Lover artist said when she showed her the song. Ethel said that year that Swift “is just sensational, inside and out.” She added, “She’s very kind and… do you know what she really is? She’s game. She had never sailed before. She sailed. She had never gone dragging before, she dragged. She played everything that everyone else was doing and she was good at it. And [with] no fuss.”
However, with young love, there ought to be some hiccups with the family. Conor and Taylor turned up to his cousin Kyle Kennedy’s wedding at the very last minute. Kyle’s mother, Vicki Kennedy, said that Conor had called her a couple of hours before the wedding, asking to attend, and she replied, “Please don’t,” concerned that the pop princess would upstage the bride. However, they appeared anyway.
“I think that story was based on the biggest misunderstanding, ’cause I would never knowingly show up somewhere that I thought I wasn’t invited to,” Swift told Rolling Stone. “And I would never want to upstage anybody.”
Swift also bought a house right across the street from the Kennedys’ legendary Hyannis Port, Mass. home while she was dating Conor. The house, which was heavily featured in the Hulu show Love Story, served as a compound for the political family. Apparently, they were all great neighbors, too!
“She’s wonderful, we’re all so happy that she’s our neighbor in Hyannis Port. She came up several weekends this summer and she was a complete participant in every single thing with our large and active family,” Kerry Kennedy, the daughter of RFK, told People in 2012. “If somebody said, ‘Lets go sailing,’ she jumped on the boat.”
“We’re jumping off the boat to swim to the break walls, holding everybody’s hands and jumping, singing, dancing, laughing, drawing pictures with everybody from the 2-year-old to my mother,” she continued. “[Taylor] is a light. And she’s a star in our family because she is a lovely, sweet, fabulous human being.”
Why did Taylor Swift & Conor Kennedy break up?
The two broke up due to scheduling. “They quietly parted ways a while ago,” a friend told Us Weekly. “It was just a distance thing. No hard feelings. They’re fine.”
“It’s been over a month since they’ve even seen each other,” the friend adds. “With her promotion for Red, she has no time off until the end of the year.”
She reflected on the relationship in an interview with Katie Couric. “I don’t know how to have a normal relationship because I try to act normal, love from a normal place, and live a normal life, but there is sort of an abnormal magnifying glass, like telescope lens, on everything that happens between me and anybody else…I don’t really know that much about love, it turns out.”
Fast forward to 2025, JFK Jr’s nephew and JFK’s grandson, Jack Schlossberg, was asked if he was jealous of his second cousin dating Taylor Swift. He told the New York Times, “Deny.”
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