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Host 1
What do you remember about Taylor Swift dating Connor Kennedy? What I remember at the time, because I was, I guess, in my early 20s, was her buying the house next to the Kennedy compound. And we were all like that. A little crazy, but also we've all done crazy things. But also the age gap thing, I didn't even clock until I was older and realizing that he was 18 when they first started dating was like, kind of worrisome. I also didn't realize until a couple of months ago that he's RFK Junior's son. I didn't clock that at the time. That's absolutely insane to learn about. Yes, I do remember them going to the grave site and I just remember the paparazzi photos and people being like, why was she there? This is kind of weird. I'm pretty sure she died by suicide.
Host 2
If I remember correctly.
Host 1
So kind of a weird time for sure.
Host 2
I'm George Severis. I'm Lyra Smith and this is United States of Kennedy, a podcast about our cultural fascination with the Kennedy dynasty. Every week we go into one aspect of the Kennedy story, and today we are talking about the Taylor Swift Kennedy era.
Host 1
Yes, an era a lot of people may have forgotten about, but a Swiftie never forgets.
Host 2
That is correct. When we say Taylor Swift's Kennedy era, we mean her documented obsession with the Kennedys around 2011, 2012, which culminated in her writing a song about RFK's widow, Ethel Kennedy, and then briefly dating RFK Jr. S son, Connor Kennedy in the summer of 2012.
Host 1
It's a modern instance where the Kennedy clan is once again at the center of pop culture, and not just because a Kennedy dated a major pop star. The various dramas that surrounded Taylor Swift's relationship with the Kennedy family at that time played out in the tabloids and online message boards, and even Kathie Lee Gifford became involved. As a bonus, it was also the first time Patrick Schwarzenegger entered the cultural conversation.
Host 2
So to break it all down, today we are talking to my favorite Swiftie, Fran Huffner. She's a senior news writer at Vulture. She writes the newsletter Fran magazine, and most importantly, she's one of the great Taylor Swift historians of our time. Fran, welcome to United States of Kennedy.
Fran Huffner
Thank you for having me.
Host 2
So let's get right down to brass tacks. Tell us about your relationship to Taylor Swift.
Fran Huffner
I got into Taylor Swift late in College, around 2011, 2012, sort of proto red era. I had no interest in her as, like, a country teen star. I felt both, like, too disconnected from that music world and too disinterested in following a blonde teenager's career. But when she started shifting to pop, and to be honest, when she started dating a Kennedy, I became very interested via a really good friend of mine in college who was like, now's a great time to get in on whatever the hell is going on with her. And I've stuck with her as Ruth, mostly thick and thin ever since.
Host 1
I do think even as somebody who's not a Swiftie, I would say I have some real solid background. Cause I'm from Nashville.
Fran Huffner
Oh, sure.
Host 1
And I actually booked her on a benefit show for the Young Democrats Club in freshman year, and she canceled. But luckily there were multiple Grammy winners as dads and moms that filled in because it's Nashville. I do think out of all of her dating stories, rumors, etc. Like, to me, this one is the kookiest and the most fun, definitely.
Fran Huffner
And it's the one that I think creates a kind of lasting impact in her identity for a while, up until Joe Alwyn, which I guess is not that long in years, but it certainly ripples throughout her general aesthetic.
Host 2
Well, it was. It's the only one I know of, or especially in that era that isn't like an A list Hollywood actor or an A list musician. Because I think of that era of Taylor as, like, I mean, right after Connor Kennedy. Correct me if I'm wrong. I think Harry Styles was right after Connor Kennedy. And so that's obviously the one that, you know, if I was writing fan fiction, that's the one I would pick as someone who is, you know, orchestrating industry plans. Obviously, I want, like, the most popular female singer to date the most popular male singer. And then people kept trying to attach her to, you know, Jake Gyllenhaal, John Mayer, like, all these A List stars. And this one almost feels like a peek into what she actually wants to sound like a crazy Stan. And I think that's maybe why people are obsessed with it. It's because it reveals something deeper about her that then was sort of never explored again in her dating history. So you said that part of what drew you to her is the fact that she dated a Kennedy. Were you independently interested in Kennedy lore or was it just a funny, you know, tabloid story?
Fran Huffner
I was studying History in college. And I think the Kennedys are a great sort of subject for a college student because they're hot and weird and vaguely cursed. And there are a lot of different routes you can go down. I didn't like specifically have a Kennedys thing, but I have friends who are really obsessed with the Kennedys. And it just sort of played into the interests of everyone I was hanging out with at the time. And it also felt to me like it was the first time Swift was making decisions for herself in a way that now we reckon with constantly. But it felt as though up to that point she was very much being managed versus the manager of her own deal.
Host 2
Totally.
Host 1
Just a little. Give a little context on who was Taylor Swift. At 22 years old, she's like coming.
Fran Huffner
Out of her ingenue status. She's pivoting away from country music. Red is kind of the country pop hybrid album that eventually cascades into her working with Jack Antonoff on 1989, which sets forward, like pop Taylor. But this is maybe also the last era where she is as approachable as she is in terms of like, she can show up at a party and it maybe not make the news, at least not immediately. But also when I was reading, reminding myself, refreshing my memory, like, she first broaches her pet interest in the Kennedys in a New Yorker interview. And I was like, she'll never speak to the New Yorker. But the idea that someone would sort of very easily be able to get a hold of her, to talk with her or to ride around in a car with her is like virtually non existent now, or reserved only only for her friends who just so happen to be writers. But this is the point at which she's making kind of a legitimacy play as an adult artist and singer songwriter.
Host 2
Yeah, it seems like it was the last time she needed the media more than the media needed her, in a sense. And you could sort of track a similar path with someone like Beyonce too. Like the Red era, from what I understand is like when she went from kind of novelty, you know, like sort of a charming young woman that was like kid friendly to like wanting to be a major pop star. So the New Yorker profile is interesting. We had in our, in our very comprehensive research doc that we have in front of us, there's an excerpt from it where she says, I'm just so obsessed with the whole history of JFK and rfk. She said she recently announced that she had completed a 900 page book called the Kennedy Women. So what do you make of her alleged Kennedy Obsession.
Fran Huffner
I think it's kind of the bridge out of her country Americana stuff into her pop Americana stuff. Like the Kennedys are so pop music. They're hot, they're maybe bisexual, you know, they're Catholic. And when she goes pop at first, she goes into this like 50s, 60s Kennedy esque, stripy bathing suit, big wide brim hat type of thing out of the like country music, thick strap, tank top, guitar vibes. So it's like the most image friendly, ideal for her to latch onto where she doesn't lose her country fans but is allowed American. She's staying American, just hopping over, taking.
Host 1
A couple steps towards the middle, I guess.
Fran Huffner
Yeah, absolutely. I always think about some old SNL sketch from like a little later than this where they're like Taylor Swift who's always in a 1950s bathing suit. And I feel like that's when like this part of Taylor comes to fruition.
Host 1
It's like Tumblr Taylor.
Fran Huffner
Yeah, it is. It's Chai. It's Chai Sugar cookie era Taylor. We're like, yeah, you. There was a world in which you could respond to Taylor Swift on Tumblr and she might then respond to you back, which now basically doesn't happen unless Treepane says it's okay for her to like comment on a TikTok.
Host 2
See, I didn't even know. I. My, my Swifty knowledge is very era specific. It's like I'm into reputation era. I will occasionally check in and see what she's up to. But I didn't even know she was on Tumblr. Sorry to any Swifties listening. That was like a whole era and she was like active on it.
Fran Huffner
Yeah. And she was posting recipes, she was responding to comments, she was like sharing memes. It was when I really started to like her because I was on Tumblr and I was like, maybe she's kind of like me. And now I understand her to be nothing like me. Though I still think we could really vibe.
Host 2
I definitely think you could. I guess I had never made that connection, but to sort of fetishize the Kennedys is a very Tumblr instinct because there's such a big part of American mythology and there are so many iconic images associated with the Kennedys. And of course Tumblr is an image based platform. Like I could see someone being super into Kennedy's fashion or different Kennedy's moments. So Taylor, the way that she gets in contact with the Kennedys is that Rory Kennedy, who is one of Bobby's daughters, one of RFK And Ethel Kennedy's daughters. And meaning she's also RFK jr's sister, reaches out because she apparently reads the New Yorker profile and asks Taylor for concert tickets for her daughters. And then that sort of develops the Kennedy connection. Then she's invited to Hannah's port. That's where she meets Connor Kennedy, who is famously 17 at the time, but then turns 18 three weeks after they meet. Even though to this day, I guess many more dramatic members of the Swiftie community say that she dated a minor, of course.
Fran Huffner
Well, with that back to back with Harry Styles. They were very upset with her at that time.
Host 2
And she's 22, we should say, at the time, I think.
Fran Huffner
Yeah.
Host 2
So basically she starts developing some sort of friendship or relationship with Connor in 2012. How is that received in the fandom?
Fran Huffner
Well, I think what's interesting first of all is in that like three week period in her sort of initial trying to like break into the Kennedys world. There's also a brief period where it looks like maybe she has a thing going with Patrick Schwarzenegger.
Host 2
Right.
Fran Huffner
Who is also Kennedy in his own way, but a kind of different flavor, shall we say, of Kennedy because of the Arnold Schwarzenegger of it all. But that winds up not happening. I believe this is before he dates Miley then. But it's interesting to think of the paths diverging. Yeah.
Host 2
And he's 18 at the time, I believe. And for anyone who doesn't know, his parents are Maria Shriver and Arnold Schwarzenegger. And at the time he was very much like an aspiring hot actor slash model. There was no prestige.
Host 1
He was a model slash actor.
Host 2
Model slash actor, you might say. Okay, so there were rumors about Patrick.
Fran Huffner
Yeah, rumors about Patrick. I think he's a better actor than model.
Host 2
Well now, now we all of course do because of the White Lotus.
Host 1
Yeah, now, yeah.
Fran Huffner
We never could have known. How did the Swifty community react to this? I can really only talk about my localized Swifty community, which to us this was hilarious, this was funny. And this is almost like before her relationships become like a total punchline. But I think it actually kind of kicks off that whole part of her star Persona because of how all in she goes on the Kennedys such that it really seems like dating Connor is a means to an end for her to become part of this family versus an actual romantic interest. It never seems like something built out of genuine love so much as it does a brand pivot, a sincere brand pivot, but nonetheless, well, in trying to.
Host 1
Give it the kindest eyes at the age difference. It's kind of like a senior in college dating a freshman in college. But the first month of college and it's like when I had friends that did things like that, it was weird.
Fran Huffner
Yeah, we all had friends, I think, who had like a slightly older partner where it's like your partner's sort of generous for that age time. Where we were like, it's not bad, but it's not great either. But I also think she at that point has a kind of arrested development that she reckons with for the next several years where she's like, am I young or am I old?
Host 2
Totally.
Fran Huffner
And you see that in the wildly oscillating between Conor Kennedy and Harry Styles versus, like John Mayer and Jake Gyllenhaal.
Host 1
Yeah.
Host 2
And I think that you could so easily argue that the narrative around the Conor Kennedy relationship, which is like she's desperate to be a Kennedy and she just wanted to date any Kennedy and this was the one that was right in front of her, you could argue that that is, you know, a little unfair to her. But unfortunately she's not doing herself any favors by first express her obsession with the Kennedy family in multiple platforms and then within months announcing that she is dating someone.
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Host 1
Okay, the other thing about this, a little bit of exposition before Taylor shows up. She meets them all on July 4th, right? July 4th, at the Kennedy compound.
Fran Huffner
Mm.
Host 1
Okay. Two months before this, Connor's mom has committed suicide. And I feel like that takes away maybe my ability to give her the benefit of the doubt. Just in terms of this is a young person who's just lost their mother in a really traumatic way. And it's seems like not a great idea for an older person to be approaching them for a romantic relationship.
Host 2
But the family is, you know, to play devil's advocate, the family is embracing Taylor. She was invited by the family to the compound. She didn't show up. Crazed and ready to be a predator.
Fran Huffner
Totally. I get the sense that her initial presence is welcome and a nice distraction perhaps from all that they have been dealing with terror.
Host 2
And again, they, I mean, Roy reached out to her because her daughters were fans and they were so sort of like starstruck by her. It really was a kind of mutual attraction. And I think for Taylor, it was so impressive to be around the Kennedys. And then for the Kennedys, they were like, this is the biggest up and coming pop star. And it's so fun that she wants to spend time with us and the Kennedys, you know, as we, as we know, have a long history of involving the celebs of their time in their public and private lives. My favorite story about Taylor at the Kennedy compound is that she decided to play her song Starlight for Ethel and the whole family. And Frank, can you tell us what Starlight is about?
Fran Huffner
Starlight is about Ethel, of course.
Host 2
And it is a fictionalized account of her love story with Bobby.
Fran Huffner
I think loosely fictionalized. I think she's pulling from the 900 page book that for the record, I believe she read all of.
Host 2
Correct. Yeah.
Fran Huffner
Because she's always kind of doing shit like this. But yeah, she writes this song, Starlight, from the point of view of Ethel and sings it to Ethel and family. And the response, I believe is not like, check out this freak. It's sort of like, that's nice, like, good for them.
Host 2
Yeah. And somehow it's funny, I was expecting, I think, people, I don't know, tabloids that wrote about it, of course, made her out to be like a psycho. But then it appears that months later, after the Connor relationship, she in fact received some sort of award at the RFK Ripple of Hope gala in New York City and performed Starlight live in front of the Kennedys. So they must have liked it to some extent.
Fran Huffner
Yeah, I think that song's fine. I have no bone to pick with that song. But I also think at that point in time, the marvel of her as a singer songwriter has yet to wear off. Where it's like, yeah, she writes all her own stuff and that's really impressive. And that she would deign to write about even just a really famous entity feels really novel and really like, oh, so, like, special even.
Host 1
So then it seems like there's a bit of a turn with her relationship with the family. And when she and Connor show up to a wedding that they're not supposed to. Could you tell us that story?
Fran Huffner
They crash. They. Well, they may or may not have crashed a wedding. I need to pull up. Who got married?
Host 2
It was Liam Kerr and Kyle Kennedy.
Fran Huffner
Right, okay.
Host 2
And Kyle is Connor's cousin. She's the daughter of Michael Kennedy and a brother of RFK Jr. Who died in a skiing accident in 1997.
Fran Huffner
Right. So they crashed this wedding. Connor, I believe. I'm putting this on Connor. No offense to Connor. Connor, I believe, is not invited, or at least Taylor is not invited. But he tells Taylor, it's fine, we can go. Which I don't think is a crazy thing for an 18 year old to think about a wedding in his family. But they show up together and it is seen as a kind of upstaging of the wedding itself. Aunt Vicky, who is the mother of the bride, gets pretty pissed off about this and gabs hard about the crashing of the wedding and makes it look as though Taylor is kind of sucking the life force out of the Kennedys for a kind of attention.
Host 2
And then Taylor, from what I understand, maintains that she was invited.
Fran Huffner
She more maintains that she never would have crashed.
Host 2
Right. That she was told she could go.
Fran Huffner
She's like, I would not have just like done this. Which also feels correct. I think she's not lying.
Host 2
Yeah.
Fran Huffner
About this. And they were probably truly under the impression that it was no big deal. Which also feels like an early reckoning with how famous she is, where she also may not have processed that her presence at an event like this with a family that is so famous in her mind, could be upstaged by her. Because I think she really does feel like she's Taking a backseat to all of their dramas and romances and stuff like that.
Host 1
We do have another person weighing in on the context later on, which is Kathie Lee Gifford.
Host 2
What did Kathie Lee Gifford say?
Host 1
She said that they crashed. She was like, it was a crash.
Host 2
And she said that, like, to the press or on tv. Okay.
Fran Huffner
I think she said it on tv.
Host 2
And then was that what sort of got the story going and got everyone talking about it?
Fran Huffner
I believe that is how it sort of then really catches fire.
Host 2
And I do want to say you mentioned that the mother of the bride, like, really was yapping all about town, and it really was like she said to the Boston Herald, she said. 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, which is so crazy, because the Kennedys are. I mean, of course, they have a complicated relationship with the press, but they generally are not giving, like, you know, controversial quotes like that about celebrities. It really feels very out of character.
Fran Huffner
Yes. And it feels out of character as a description of Taylor, which is not to say that it's not true. I don't know that I totally buy it, but her image is really controlled, even back then. And she rarely, if ever, appears as someone disinterested or rude. Like, if nothing else, like, she's always crazy polite, and that's all anyone ever has to say about her. So this both, like, shatters and perpetuates an image that she's, like, constantly working and fighting against, both in just, like, how she seems to be out and about in the world and in the sort of bigger brand of her star.
Host 1
Yeah, this is kind of the point. Like you were saying before, she needs the media more than the media needs her. There's also this. This very same weekend of the wedding, she and Connor go to visit his mother's grave site as she has committed suicide just two months earlier.
Fran Huffner
This is the actual egregious thing, I think, in this relationship is the paparazzi visit to Connor's mother's grave. Just because I am a paparazzi skeptic, Right. I never believed the paparazzi just happened to be anywhere, let alone, say, a cemetery such that. I find this quite craven.
Host 2
So the accusation, of course, is that Taylor called the paparazzi to take photos of her and Connor visiting Connor's mother's grave two Months after she had passed.
Fran Huffner
That's right. They're hugging and he's looking very sad.
Host 2
And she helped clear some overgrown brush from around the gravestone. It's like she's really participating in the performance.
Fran Huffner
She's in like a little sundress, her lipstick. She's in like Taylor Swift costume basically.
Host 1
And this is something we'll definitely talk about when we get to RFK Jr. But a little bit of context too on this grave site is that after her funeral and initial burial at the Kennedy graveyard, he in the middle of the night has her coffin dug up and moved with no headstone, facing the highway, 80 yards away or something. And so that's why there's overgrown. Like he put her in an unmarked grave.
Host 2
Why did he do that?
Host 1
Well, because he tortured her for many years. And he said after the burial, he said that he didn't realize how crowded the Kennedy graveyard was, so he had to make more room. So he just got her up in the middle of the night and pushed her out. It's very strange. And all this is going on and their 18 year old son is dating a 22 year old pop star and they're taking paparazzi photos at this grave site that's barely a grave site right now. It's a pretty wild situation when you think about the full Kennedy context.
Host 2
So to me, the sort of trifecta of controversies with the Conor Kennedy era are crashing the wedding, paparazzi at the gravestone. And then the third one to me, which is kind of my favorite, is her buying a house across from the Kennedy compound. So Fran, what is the deal with that?
Fran Huffner
There's a sort of cul de sac in, in Massachusetts where several of the houses in this cul de sac belong to the Kennedys. And one of the houses that just so happens to be available gets snatched up by Taylor Swift. And in the way that kind of like all the Kardashians live down the block from each other so they can just drift in and out of each other's sparse mansions. She moves in like no joke across the street from the Kennedy compound. Like could wave from a window, not a metaphorical across the street or five minute walk away, like truly across the way, as if to basically be like, yeah, I'm thinking I'm staying here for a little while. And also seems to be like a pretty early flecks of wealth on her behalf that she's, you know, 22 at this point and can afford this giant house in a state that she is not sort of using as Like a vehicle for fame. It's not Nashville, it's not la. It's not New York. It's a place she really does not have to be, except for her Kennedy thing. And she plants herself there and she's.
Host 1
I mean, the other thing about Taylor Swift today is like her real estate portfolio on its own is like rivals. People entire lives are devoted to.
Host 2
She's a regular Ellen DeGeneres.
Fran Huffner
Yeah.
Host 1
And this is like purchased through a shell company. And her argument, or the argument of maybe, like the people around her at the time was like she was looking at lots of investment properties. And she had been at this one for a while. But it is very odd timing. She buys it while they're dating. Like, the short, short, short period of time that they're dating is when she closes on the house. And it's a four and a half million dollar house.
Fran Huffner
It's not a quick process necessarily to buy a house either, unless you pay cash, which I have to imagine she did for this house.
Host 2
And her side of the story, I guess, or her team side of the story, as Lyra said, is that she just wanted to buy an investment property. And in fact, allegedly it was recommended to her by Rory ke, which makes it a little more believable. It's like Rory knew that there were these properties available in that area because she knows the area, and then Taylor went ahead and bought it. I should also say, you know, the story has a really happy ending because she actually sold the house in March of 2013 for $5.6 million and collected a nice check from flipping the property. So all's well that ends well.
Fran Huffner
Yay. I'm so glad she winds up getting a big house in Rhode island that is still very essential to her Persona and her personality and her sort of infamous fourth of July Rhode island house party that I think is born out of having attended the Kennedy one and her being like, well, I'm gonna do my version of that every year, but with Blake Lively and Selena Gomez.
Host 2
Totally.
Host 1
Tom Hiddleston.
Fran Huffner
And Tom Hiddleston.
Host 1
I love TS shirts.
Fran Huffner
I heart ts.
Host 1
I remember these things. I was, you know, I was following the celebrity gossip blogs at this time, and I think that that is maybe my sole understanding of Taylor Swift at this period of time. For the next probably like five years.
Host 2
It's a nostalgic time because it was, you know, it was before she was too big to fail. You really got the sense that she was still in progress. Like she hadn't decided where she was landing. As a public figure, I Also feel like there's this thing that Taylor does. And, Fran, I would love your take on this, which is, like, intentionally fanning rumors about her love life and then being defensive about the sort of offensive coverage of it. So she's, like, constantly writing songs about different famous guys or, like, being seen with them, clearly intentionally in public. Then she'll see a story on Us Weekly that's like, wow, Taylor Swift has dated seven guys in one year. And then she'll be like, here comes the sexist media again, trying to make me out to be this promiscuous, like, gal about town. Like, for example, with this house thing. Apparently she told Vanity Fair, people say that about me, that I apparently buy houses near every boy I like. That's the thing I apparently do. If I like you, I will apparently buy up the real estate market just to freak you out so you leave me. Which is like attacking them for covering this. But in fact, she did do that.
Fran Huffner
Yeah. No, completely. This is. Yes, she does this all the time. I always think about when she got mad at Ginny and Georgia, a Netflix show that no one I know has ever watched but is seemingly extremely popular, where I think they made a joke of, like, more this than boyfriends of Taylor Swift. And she did one of her rare tweets where she dug in, not necessarily to Ginny and Georgia, but to Netflix the company, as though Netflix the company. This was like, a statement from Netflix the company. Because her documentary Miss Americana was also a Netflix release. And I think she positioned it more like, as, like, a personal betrayal from one corporation to another. All Considered. But the Ginny and Georgia joke is both, like, observed and completely toothless. But she will take any opportunity to garner a kind of sympathy.
Host 1
I thought you were gonna say the Tina Fey, Amy Poehler joke where she said, there's a special place in hell for women who make fun of other women. It's like they're hosting an award show. They're making fun of everybody. It was not a shocking thing.
Fran Huffner
Right. In sort of her relationship to the media, she proves kind of over and over again a lack of a sense of humor. But then when her friends get interviewed, the Himes and Lorde and Selena Gomez or whoever, they're always like, and Taylor is the funniest person of all time. And it's like, well, that can't be true. I'm willing to believe that she's fun to hang out with, but I will not believe that this is one of the funniest people, because she really cannot take a joke about this aspect of her life. But I also wonder if that's changing for her post poets department because that was a sort of strangely self aware and self kind of derisive album about her many manias where she seemed to be actually like reckoning with the parts of herself that she doesn't like more than blaming other people.
Host 1
I mean to be fair, to be a 14 year old girl when you get started and be under the microscope like that for a decade plus before you get to the point where you can laugh about it. Yeah, I don't know.
Fran Huffner
I've never been there.
Host 1
Maybe it does take that long. But it is shocking. I don't know, I just think I'm always surprised when a person who is in attendance at an award show, a person who is that privileged and accomplished and you know, fortunate then is offended. That there was like a one liner thrown in their direction is just kind of shocking to me.
Fran Huffner
I know. But it led to the slap.
Host 2
So it's like again, all's well that ends well. Taylor Swift made a profit from selling the house and we got the slap. So what more does everyone want.
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Host 2
To close the loop on Connor, though. Fran, I want you to tell us, how long did this relationship last?
Fran Huffner
Two and a half months.
Host 2
Correct. So all of this, everything we're saying happened in the span of two and a half months, including the paparazzi photos. Crashing the wedding, like, her buying a house, her giving multiple statements to Vanity Fair. All of this was in the span of two and a half months. And then I believe, you know, sort of going through the timeline in my head in real time. If they met July 4, it sort of lasted through, like, August, maybe September. And then apparently she started dating Harry Styles in December of 2012 of that year.
Fran Huffner
Yeah, well, because they have the winter romance as reflected upon in 1989. Snowmobile. That's the cold weather album. And then Red is sort of a summer album.
Host 2
Oh, interesting.
Fran Huffner
This is also, I guess, like, 2012 to 2016 is the last good era of Taylor Swift paparazzi photos. Because there's the grave paparazzi photos with Connor. There's, like, when Harry Styles left her on a boat. Her sitting on the boat alone is a great photo. And then it sort of culminates with, like, all the Tom Hiddleston stuff. Most notably, to me, not the Fourth of July party, but when they're on, like, a hike on the rocks and she's dressed like a grandmother who has to be, like, helped along. Now she'll just go out to dinner for the rest of her life. There's no funny paparazzi photos.
Host 2
Yeah, no, it's just Via Corona every single night with Blake Lively. And we better be satisfied with what we're getting. Yeah.
Host 1
And I was standing behind her and Jake Gyllenhaal in line getting coffee in Nashville. And I had no idea the check that was standing right in front of me. If I could have gotten a photo and sold it to the gossip blog.
Fran Huffner
What was their vibe?
Host 1
Oh, first I didn't recognize her at all. Cause she just looked like a regular college girl in Nashville. And this was really like our college coffee shop. And I noticed Jake Gyllenhaal. Cause he's Jake Gyllenhaal. Also, I'm just realizing that my other celebrity sighting at that coffee shop was Kirsten Dunn.
Fran Huffner
Wow. Now there's a Miss Americana.
Host 2
I know. I gotta visit that coffee shop. And actually, there's another person that dated Jake Gyllenhaal.
Host 1
Yeah, that's what I was saying.
Fran Huffner
Like, it's, like, full.
Host 1
You know, they have a lot of things in common.
Fran Huffner
This is so besides the point. But my friend who teaches high school took his students to see the Denzel Washington, Jake Gyllenhaal Othello because there were, like, the student tickets. And I was like, do your high school students, like, know who Jake Gyllenhaal is? And he was like, no, they have no idea who this is. Like, he's not famous to them. I was like, that's crazy.
Host 2
This is why we have to do this podcast about the Kennedys, because the only monoculture left is the Kennedys. It is the only thing everyone at least can recognize as a name.
Fran Huffner
Absolutely.
Host 2
I do want to say, you know, talking about all these people again in 2013 in Vanity Fair, Taylor basically said, I've dated exactly two people since 2010, I guess, meaning Connor Kennedy and Harry Styles. So basically, she sort of is implying that, like, all these other ones are, like, people she had coffee with once or, like, was seen with once, and she thinks it's offensive that there are these carousels with her with various men because she only dated two people between 2010 and 2013.
Fran Huffner
I do think the culture was much meaner about her having multiple boyfriends. I think if she was a sort of Sabrina Carpenter ish figure, people would care much less or it would be, like, good for you, girly. But it does become this sticking point that she doesn't drop even when the culture changes, because it did happen to her in that moment. But I also think like. Like, celebrities get frozen in the time in which they become famous, which is why there is this perpetually kind of cringe 2010 ness to her that makes people a specific kind of insane.
Host 2
Well, and I also. You were talking about her sense of humor, and I think her sense of humor to me, comes out so well in, you know, I'm the problem. It's me in that song, which is called what?
Fran Huffner
Anti Hero.
Host 2
Anti Hero, yeah. And the humor in which, by the way, that song, I am only slightly ashamed to say, was my number one most played song that year on Spotify. So I know the lyrics very well, but the humor in that song is so 2000-10-10th millennial Blurg, you know, has rewatched, you know, the office in 30 Rock. And I'm in no way implying 30 Rock is cringe. It is literally my favorite comedy on television. But it is, you know, the references are sort of like 2010s references in this Very kind of like, funny way. And I actually think even more than that, something that is both frustrating and also charming about Taylor is that sort of all her references are dated. Even her album covers, the aesthetics of them are always one sort of three year period too late. Like that 1989 is this like Polaroid photo that was already washed at the time. That's like Hipstamatic prints.
Fran Huffner
I know. I personally love it about her because it sort of reflects. I think she's sort of very open about it and would not claim to be up on anything. And sometimes she feigns this sort of like, I'm just an old woman deep down. And that's where I'm like, yeah, you are.
Host 2
Exactly. Even her thing about being a cat lady, like, she's. That's another kind of like millennial tinged trope.
Fran Huffner
Yeah. Like, there's a lot of pop stars and I think celebrities who are just gonna be feeling like the long tail of Brat, where Brat will have like, kind of fucked up their next five years. Comparatively, we don't have to worry about that with Taylor at all. Taylor's identity is clear. It's been clear. It might be very mockable, but it is consistent.
Host 2
I do want to say the closest she's gotten to Brett is Reputation, which is my favorite era. And, you know, she's no Charli xcx, but some of those songs really, really still slap. Yeah.
Fran Huffner
Well, I think her with the Taylor's versions being like, I actually don't want to touch Reputation was a fascinating and I think ultimately correct play.
Host 1
Yes. The one thing I wanted to add that we missed. Ethel Kennedy is asked, do you think they're going to get married? As we know, in so many words. And Ethel Kennedy says, we would be so lucky. Which is a. It's, you know, very nice thing to say. Also, we're talking about children here, basically, and it's very strange that that would even be a question. They've been dating for like, let's say three weeks at that point. One month.
Fran Huffner
Maybe they're Catholics. Like, that's when they start thinking about that.
Host 2
Yeah. No, they're like, the clock is ticking. No. And I, again, this is like a recurring thing. All the Kennedys loved her. Like, the only one that of course did not is the mother of the bride at the wedding who is, you know, going around town saying that Taylor is dead behind the eyes and it's like talking to a ghost. But all the other ones, I mean, you know, again, she was invited to perform at that RFK Junior gala. You know, this was before he went maga. One thing I'm realizing only in having this conversation is what is the deal with. We're now skipping many years ahead, the last great American Dynasty. Because that song is about the Kennedys, right?
Fran Huffner
Sort of. Okay, sort of is my understanding. I mean, yes, but I think about, like, her in there. She's sort of taking the concept of like Kennedy iconography, but with like a sort of like fictionalized version of herself. Like, that album is more about, like versions of Taylor. More so than she's like, casting out or like reflecting on like Ethel or, I don't know, JFK Jr. Or anything like that. And it's, you know, it's about a sort of preppy Rhode island woman who sort of got a whole thing going on and being like, heir to a lot of money. But the one to ones with Kennedys, like, don't really lineup. I think she's just sort of conceptually taking the idea of American Dynasty, which she got from the Kennedys, and reapplying it. But so much of that album is a kind of like auto fiction project. Right.
Host 2
Because there's that line, she had a marvelous time ruining everything. And I. It obviously, without having done any research about it, I thought maybe that's referencing this trope of Taylor going into Hyannis Port and wreaking havoc or even crashing the wedding or whatever.
Fran Huffner
Yeah. I think it's sort of drawing from like all this stuff that era to me always feels like. Cause she's like, deep in the Joe Alwyn relationship. I was like. And of course she's pulling from Joanna Hogg's souvenir films by expounding auto fictionally about her life. But it does feel like that and evermore are harder to nail down to. Like one thing before we end, I.
Host 2
Do want to say, Fran, you, I think are the person that told me Conor Kennedy went to fight in Ukraine.
Fran Huffner
That's right. That's the last I heard about him. Because I had. I had felt. And this is like not. Not so, so recent.
Host 2
I believe it was 2022.
Fran Huffner
Yes. Where I feel like none of us had heard about him post Taylor Swift breakup. That's fine. Maybe he wants to be as much of a civilian as a Kennedy can be a civilian. But he sort of reemerges fall of 2022 to just be like, by the way, I went to Ukraine to like fight in Ukraine. And it's like, what you did? And he has this like, long Instagram post where he basically says he went there like, kind of anonymously. Like, he didn't really tell a lot of family and friends. He didn't tell people there, like, who he was related to and how he felt like it was a cause he really had to get behind. He says this war will shape the fate of democracy in this century. And it's like, maybe, but I didn't know that's something this guy cared about.
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Wow.
Fran Huffner
And now he's just, like, engaged and back stateside.
Host 1
Yeah. To a singer songwriter.
Host 2
Yes. A Brazilian singer songwriter, Julia B.
Host 1
We might be seeing him on the ballot someday.
Fran Huffner
Yeah.
Host 2
He is really the dark horse of the Kennedys because we just did a whole episode about Jack Schlossberg, who I think is now carrying the mantle of the quintessential millennial Kennedy. But, you know, at any point, Connor could enter the arena again and in fact, you know, use his experience in Ukraine as kind of something that sets him apart.
Host 1
I mean, that's quite a bit more experience in politics than Vogue's political consultant for four weeks.
Host 2
Yes, exactly. All right, so, well, I just want to say we here at United States of Kennedy will be keeping an eye out for all these millennial Kennedys, and we will be doing an official ranking at some point. Fran, thank you so much for chatting with us about Taylor Swift and Connor Kennedy. I'm honestly now really in the mood to go and listen to Red Taylor's version.
Fran Huffner
It's good.
Host 2
Good.
Fran Huffner
It's really good. It's the best. Taylor's version, I think.
Host 2
There you have it. All right, thanks so much.
Fran Huffner
Thank you.
Host 1
That's it for this week's episode.
Host 2
Coming up this season, we will be talking about Bobby Kennedy taking on Jimmy Hoffa, the iconic documentary Gray Gardens, the many faces of RFK Jr. And the heyday of George magazine.
Host 1
So subscribe and follow United States of Kennedy for all things Kennedy. Every week.
Host 2
Talk about stepping up.
Fran Huffner
It's time to level up your game.
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Fran Huffner
Off terms apply this Labor Day.
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Host 1
Every day has a to do list.
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Podcast: United States of Kennedy
Episode Date: August 25, 2025
Hosts: Lyra Smith & George Civeris
Guest: Fran Hoepfner, senior news writer at Vulture
This episode dives into Taylor Swift’s intense but brief “Kennedy era” in 2012, focusing on her relationship with Conor Kennedy, her larger fascination with the Kennedy family, and how this saga became a pop culture touchstone. With guest Fran Hoepfner—a self-described “Taylor Swift historian”—George and Lyra examine the dynamics of celebrity, the mythology of the Kennedys, and Taylor’s evolution from country ingénue to pop cultural epicenter.
For fans of Swift, Kennedy lore, or the nexus of fame and American history, this episode delivers equal measures gossip, cultural analysis, and nostalgia.