Taylor Swift's Forgotten Relationship With Conor Kennedy Was Filled With Controversy

Summary

• Taylor Swift's string of high-profile relationships often ends up mired in controversy, including her romance with Conor Kennedy in 2012.
• Fans raised eyebrows over the age gap between Swift and Kennedy, as well as Swift purchasing a mansion near Kennedy's family.
• The relationship faced even more drama when Swift was accused of "kidnapping" Kennedy and crashing a Kennedy family wedding.

Though truly remarkable, Taylor Swift’s wildly successful music career isn’t the sole reason she’s almost always in the headlines. The singer-songwriter has also evoked widespread public attention for her string of heavily-publicized, whirlwind relationships.

And if fans have learned anything from Swift’s bombshell album, 'The Tortured Poets Department', in which she eviscerates several of her famous ex-boyfriends, it’s that controversy is never far off when it comes to her dating life.

However, none of Swift’s dating controversies have stirred the pot quite like her 2012 romance with Conor Kennedy. In this article, we’ll delve into the 'Blank Space' singer’s fleeting affair with the Kennedy heir, and why it ended up causing a stir for being ‘inappropriate.’

Fans Were Concerned About Taylor Swift’s And Conor Kennedy’s 'Inappropriate' Age Gap

With a staggering fourteen Grammy Awards under her belt and a spot among the best-selling artists in the world, it’s no wonder Taylor Swift has been the subject of widespread fascination ever since she shot to fame with her chart-topping albums ‘Taylor Swift’ and ‘Fearless’ in the 2000s. Much of the credit for the singer-songwriter’s notoriety, however, is owed to her dating life.

From controversial rockstar Matty Healy to film star and songwriter Joe Alwyn, Swift has had a string of pretty high-profile romances in her decades-long career. Though the ‘Blank Space’ singer’s romances almost always end up mired in controversy, none has raised quite as many eyebrows as her months-long romance with Conor Kennedy.

Rumors that the two were an item started swirling in late July 2012 when Swift, then 22, was spotted packing some serious PDA with Conor in Massachusetts, barely a week after the Kennedy heir turned 18. "Conor put his arm around Taylor, and they kissed behind the boat shed," an eyewitness told US Weekly at the time.

A week later, news outlets confirmed that the two were officially dating, marking the start of a social media controversy that’s yet to die down. Despite the two having called it quits over a decade ago, X users were still slamming Swift for the relationship as recently as May 2024.

“I just realized that not only did Taylor swift start dating 18yo Conor Kennedy when she was 22, but it was ALSO like, not even a month after his mother committed suicide??? Wtf,” one fan wrote on X in May 2024.

The months-long relationship was also the subject of an intense debate on Reddit in February 2024, and yet again, fans were concerned about the duo’s age difference at the time.

“[I don’t care] what anyone says this is weird. A 22 [year] old and a just turned 18 [year] old? I'm 21 and would not date someone still in school. It's just strange. I don't think it's necessarily [wrong] but if someone I knew did it I'd think they were weird.”

Taylor Swift Raised Brows After Purchasing A $4.9 Million Mansion Next Door To Conor Kennedy

But it wasn’t just the age difference between Kennedy and Swift that raised eyebrows. Swift also found herself on the wrong side of public opinion when she reportedly bought a $4.9 million mansion right across the street from Kennedy’s grandmother, Ethel, mere weeks into the relationship.

And it wasn’t just fans who were baffled by Swift’s grand gesture. According to J. Randy Taraborrelli’s ‘The Kennedy Heirs’, Conor wasn’t particularly thrilled with the purchase either.

“Conor liked Taylor, don’t get me wrong,” Conor’s friend shared in the book, “but this business of her buying the house on the Cape made him nervous. It seemed as if she was getting a little too attached, spending five million bucks on a house just to be near the guy.”

The two ignited even more controversy mere weeks later when reports surfaced that Swift had “kidnapped” Kennedy from his private boarding school in Hyannis Port, Massachusetts, whisking him off to Nashville on a private jet—all without his parents' knowledge.

An anonymous insider revealed to PageSix:

“Taylor missed Conor so much, she sent a plane for him a few days later. He’s been with her ever since, and his family doesn’t know when he will be back. Things have become so serious between them so fast that no one in Hyannis Port would be surprised if they eloped.”

Swift commented on the allegation months later in an interview with RollingStone:

“How did I kidnap him? You can’t kidnap a grown man! These are serious accusations, now!”

Taylor Swift And Conor Kennedy Roused Controversy After Allegedly Crashing A Kennedy Family Event

Just a month before parting ways, Kennedy and Swift found themselves entangled in yet another scandal. This time, Swift had allegedly crashed Kyle Kennedy and Liam Kerr’s wedding at the Fairmont Copley Plaza hotel and had to be ousted not once, but twice by Kyle’s mother, Victoria Gifford Kennedy.

Victoria confirmed the news to the Boston Herald just days later:

“They texted me an hour before the wedding and asked if they could come. I responded with a very clear, ‘Please do not come.’ They came anyway. I personally went up to Ms. Swift, whose entrance distracted the entire event, politely introduced myself to her, and asked her as nicely as I could to leave. It was like talking to a ghost. She seemed to look right past me.”

Swift commented on the controversy months later in her interview with RollingStone:

“I have no idea what happened there. 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. And I would never want to upstage anybody.”