Conor Kennedy was ‘nervous’ when Taylor Swift real-estate stalked him

Taylor Swift

I’ve been saying for a while now that I miss 2016 Taylor Swift, because that was so much fun – the international love tour with Tom Hiddleston, Tiddles in England, Tiddles in Australia, Tiddles in LA, swan pastries and summer of receipts and all of that. It really was a great moment in gossip. But it was not her messiest gossip moment. No, Taylor Swift’s biggest mess was in 2012, when she briefly romanced Conor Kennedy, who was then an 18-year-old high school junior attending a fancy boarding school (she was 22, almost 23). She met him the summer of 2012, shortly after his mother killed herself, and she quickly went overboard, buying a house close to the Kennedy compound (and lying about it) and dropping by his boarding school to sign him out for the weekend so they could go antiquing in New England. Then as suddenly as it began, it was over and she was with Harry Styles. As I said, that was pretty much her Peak Messiness.

What was funny was that Taylor lied about buying property next to the Kennedy compound for months and months, and then Vanity Fair pulled out the receipts about how she actually did buy the property (while she dated Conor) and she later flipped it for a profit. That story is part of a new book about the Kennedys.

Taylor Swift needed to calm down. During the pop star’s short-lived romance with Conor Kennedy in 2012, she bought a house in Hyannis Port, Massachusetts, mere weeks after meeting him — and the purchase made the then 18-year-old “nervous,” according to a new book.

The Kennedy Heirs by J. Randy Taraborrelli details the summer fling the songstress, now 29, had with the son of Robert F. Kennedy Jr., including how tragedy brought them closer together and the musician’s surprising real estate purchase.

“Taylor was saddened when she heard the details of how Mary Kennedy had died,” Taraborrelli wrote about Conor’s mother death by suicide two months prior. “She was close to her own mother and couldn’t imagine how Conor was able to go on after facing such tragedy. She admired his strength, his resolve.”

The intense intimacy may have led Swift to make a grand gesture. After just six weeks together, she bought a $5 million house near the Kennedy compound, according to the book. “Conor liked Taylor, don’t get me wrong,” Conor’s friend told the author, “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.”

[From Us Weekly]

Yeah. It was too much. I also remember when Taylor and Conor got pap’d at his mother’s grave and the whole thing just felt so icky. I remember there were actual political commentators talking about how inappropriate it all was, and how it felt like Taylor was trying to hack into “Camelot.” As I said though, she seemed to come to her senses after a few months and I don’t even think she’s made any public (or lyrical) references to her late-summer fling with Conor. Maybe she realized that she really overstepped in about 10 different ways – buying the house in Hyannis Port, stalking him at boarding school, lying about the house purchase, pap strolling at his mother’s grave… it was all terrible.

The Kennedys celebrate Independence Day

Photos courtesy of WENN.

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27 Responses to “Conor Kennedy was ‘nervous’ when Taylor Swift real-estate stalked him”

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  1. Arizona says:

    I’m pretty sure Starlight was written about Conor’s grandmother, and was written after they had their fling. I think Begin Again was also suspected to be written about Conor.

    It drove me nuts that she tried to make it sound like the media was just being terrible and making her sound like a crazy stalker who buys houses near dudes she just met – when that’s what she actually did! But she tends to change the narrative around her to always make herself be the victim, rather than own up to her actions. Sigh.

  2. Angel says:

    I’m glad that she is calmer about things now.

    That shade of blonde is different. She looks better with her old shade; it used to be perfect for her complexion, but that shade is too brassy.

  3. SamC says:

    My biggest takeaways were 1-surprise that he was 18 and only a junior in high school (yet also got into Harvard?) and 2-she does really well in her real estate transactions as she flipped it for a profit

    • Appla says:

      Didn’t his mum commit suicide not long before he dated Taylor Swift? His father was quite a philander

    • DS9 says:

      If you take a child with a late birthday and red shirt them, this is what you get.

      Also, you can be held back a grade and still get into Harvard if you’re a nobody and this kid is a Kennedy.

      On topic, I’ve never forgotten this grossness. I did not realize though that it was so close to his mother’s death

      • Megan says:

        IIRC, he was 18 when he was a junior because he had been absent from school the prior year because neither parent registered him. I suspect he’s had a tough childhood.

    • K-Peace says:

      I remember this whole gossip story very well and i specifically remember that Conor was a minor when she was dating him.–He was only 17. An almost-23-year-old dating a 17-year-old high school student. It seemed SO icky & highly inappropriate. It seemed like Taylor was desperately trying to become part of The Kennedys any which way she could. Yuck.

      • Meg says:

        Her wearing retro clothes during the period including a swimsuit made me think she was cosplaying 60s Kennedy’s too

      • Tater tot says:

        Then she immediately dated Harry Styles, another 18 year old! Wrote a whole album about “Harry”, when they barely dated two months. She was really icky during this time.

      • Jess says:

        This whole story is so sad (on his part) and gross on her part. Wasn’t it this icky dating situation that led Tina and Amy to make a joke about Taylor stalking some celebrity’s kid (I wanna say Michael J Fox’s kid?) at the Golden Globes? And then Taylor made herself a victim again, pulling out the “special circle of hell for women who attack other women” (I’m poorly paraphrasing) quote as if people should feel bad for her because Tina and Amy called out her grossness.

      • DS9 says:

        My eldest child is 17 and a rising freshman.

        I cannot fathom.

      • ElleKaye says:

        @ Jess,

        You are correct, I didn’t see your comment and made reference to the same thing; it was Michael J Fox. Swift then said there was a special place in hell for women who didn’t support each other.

        She can’t date a youngster, buy a house next door after a few months (and deny it), and think she won’t get jokes made about her. Especially when she chronicles her dating life in her songs.

      • otaku fairy... says:

        Unpopular opinion, but at that point I don’t even have a problem with teens being allowed to date someone a little older as long as the age gap isn’t any bigger than that. But it needs to apply not just to one gender or sexual orientation. Ironically, I think that May-December romance would have caused more lasting outrage and even some actual misogyny toward Swift if she were the 17-year-old and the guy was 5 years older, or if she had been 17 and in a same-sex relationship with another woman (plus homophobia).

        The rest of her behavior around the situation was bizarre and messy though.

      • Jess says:

        Thanks, Ellekaye! Always happy to get confirmation I’m not totally insane yet!

    • Louise177 says:

      I thought Conner was 17. I’m pretty sure that was what everyone was reporting back then. To me it was creepy that Taylor had to sign him out of school. Which is why it seems weird that she would do that for an 18 year old.

    • ElleKaye says:

      He turned 18 at the end of July, so Taylor was seeing him when he was still 17. There are pictures of them together days after his birthday holding hands and kissing in MA. That is why Tina Fey and Amy Poehler joked about her going after Michael Fox’s’ son.

  4. Cindy says:

    I’ll just say her hair looks great on that first pic. It frames her face very well. She looks like a barbie (frozen expression and everything).

  5. Mumbles says:

    I still LOL how Taylor crashed the wedding of Conor’s cousin as his date, and the cousin’s mom (Vicki Gifford Kennedy) politely asked her to leave. And according to Vicki, Taylor looked at her like she had two heads. Probably the first person to say no to her since she was 16.

    • Megan says:

      Wow, I had not heard that before. How rude!

      • ToiFilles says:

        I remember when the Kennedy Mother of Bride was coming under fire from the fan base. She countered; 1) Conor had not RSVPd, 2) The pap storm was growing upon their arrival & she had not staffed for that kind of crowd control, 3) When she told them it was becoming unmanageable & they needed to leave, TS looked right through her and walked in anyway.

        And those pics of TS in a summer frock, head bowed at the grave site of Mom of new teenage bf was such bizarre optics. You can’t convince me she wasn’t aware the paps would be there. But her fans just ate it up.

        Edit: for clarity on abbreviations MoB

    • Mumbles says:

      Thanks Toifilles for those additional details. If the paps were there, TS must have contacted them. Gross.

      I also remember Vicki Kennedy saying that her daughter had never met Swift and Mom didn’t want all the attention being stolen by TS at the couple’s expense. Imagine being upstaged at your wedding by someone you never met.

  6. Stephanie says:

    Poor Conor, Taylor Swift sounded like a stalker

  7. Meganbot2000 says:

    I fell madly in love with basically the first person I met who was nice to me after my mother died. Fortunately that person turned out to be amazing and is still one of my closest friends, but it’s such an intensely vulnerable time. I can’t imagine what it would be like to go through that as a teenager and maybe with a less than ideal family situation.

  8. KidV says:

    TBH, I would have bought that house, too. It’s gorgeous. And I wouldn’t have sold it. Dump the guy, but not the house.

  9. Ref7 says:

    Looking glassy-eyed.

  10. whatidontknowIDK says:

    Here’s the thing: No one who with or adjacent to fame dates Taylor Swift without it being a Mutual Promotion Opportunity. It’s more likely that this was a PR relationship that his team and her team worked out to cover a shrewd investment and help him launch his life as a public figure who was coming of age. All it takes is a quick Google to see their photos together are always “pap” shots that are art directed and intentional… and plastered everywhere. Definitely icky that he was 17 when they inked the deal and waited until days after his birthday to do the official roll-out.

    …also, Taylor wouldn’t have known how to go about showing up for a wedding without Conor bringing her along, so it doesn’t seem fair to blame her for being rude. Anyone who doesn’t RSVP to a wedding yet shows up WITH A PLUS ONE is 100% R-U-D-E. And the boy who wants his name in papers next to Taylor Swifts at the expense of his cousin is THE WORST.

    • ToiFilles says:

      “…also, Taylor wouldn’t have known how to go about showing up for a wedding without Conor bringing her along, so it doesn’t seem fair to blame her for being rude.”

      You are leaving out that the bride’s mother / Vicky Kennedy asked them to leave the reception when it became obvious that the media attention was becoming unmanageable. TS should have had the maturity to recognize the situation and graciously leave. Yet she walked right past ** – which qualifies as rude. As a famous person who experiences crowd control, TS does share some blame on that one.

      ** which Kathie Lee Gifford stated on her Today Show segment.