All Episodes

August 25, 2025 • 39 mins

Taylor Swift’s fascination with the Kennedys is well documented, but it really reached a fever pitch in the summer of 2012 when she briefly dated RFK Jr’s son Conor Kennedy. Today, we’re joined by Vulture staff writer and Taylor Swift historian Fran Hoepfner to break down Taylor’s top Kennedy moments, from an infamous paparazzi scandal to a mysterious real estate purchase.

See omnystudio.com/listener for privacy information.

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:09):
What do you remember about Taylor Swift dating Connor Kennedy.

Speaker 2 (00:14):
What I remember at the time because I was, I
guess in my early twenties, was her buying the house
next to the Kennedy compound, and we were all like
the anitted but also we've all done crazy things. But
also the age gap thing, I didn't even clock until
I was older, and then realizing that he.

Speaker 3 (00:32):
Was eighteen when they first started dating was like kind
of worrisome.

Speaker 2 (00:35):
I also didn't realize until a couple of months ago
that he's.

Speaker 3 (00:39):
RFK junior son. I didn't clock that at the time.
That's absolutely insane to learn about.

Speaker 2 (00:44):
Yet I do remember them going to the grave site,
and I just remember the paparazzi photos and people being like,
why was she there?

Speaker 3 (00:51):
This is kind of weird. I'm pretty sure she died
by suicide if I remember correctly, so kind of a
weird time for sure.

Speaker 4 (01:06):
I'm George Severes, 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.

Speaker 1 (01:22):
Yes, an era a lot of people may have forgotten about,
but a Swifty never forgets.

Speaker 4 (01:28):
That is correct. When we say Taylor Swift's Kennedy era,
we mean her documented obsession with the Kennedys around twenty
eleven twenty twelve, which culminated in her writing a song
about rfk's widow, Ethel Kennedy and then briefly dating RFK
Junior's son, Connor Kennedy in the summer of twenty twelve.

Speaker 1 (01:46):
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 I played out in the tabloids and
online message boards, and even Kathy Lee Gifford became involved.

(02:06):
As a bonus, it was also the first time Patrick
Schwarzenegger entered the cultural conversation.

Speaker 4 (02:11):
So to break it all down today, we are talking
to my favorite Swift, Ye Fran Houffner. She's a senior
newswriter 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 the United States of Kennedy.

Speaker 3 (02:26):
Thank you for having me.

Speaker 4 (02:27):
So let's get right down to brass tacks. Tell us
about your relationship to Taylor Swift.

Speaker 5 (02:33):
I got into Taylor Swift late in college, around twenty
eleven twenty twelve.

Speaker 3 (02:40):
Sort of proto red era.

Speaker 5 (02:43):
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 up blonde teenager's career.
But when she started shifting to pop, and to be honest,
when she started dating at Kennedy, I became very interested

(03:03):
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 mostly thick and than ever since.

Speaker 1 (03:14):
I do think, even as somebody who's not a Swifty,
I would say I have some real solid background because
I'm from Nashville, Oh sure.

Speaker 3 (03:23):
And I actually booked.

Speaker 1 (03:24):
Her on a benefit show for the Young Democrats Clubs
WOW in freshman year, and she canceled, but luckily there
were multiple Grammy Winners as dads and moms that filled
in because it's Nashville.

Speaker 3 (03:36):
I do think, out of.

Speaker 1 (03:37):
All of her dating stories, rumors, etc. Like to me,
this one is the kookiest and the most fun.

Speaker 5 (03:45):
Definitely, and it's the one that I think creates a
kind of lasting impact in her identity for a while
up until Joe Alwin, which I guess is not that
long in years, but it certainly ripples throughout her general esthetic.

Speaker 4 (04:00):
Well, 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 yeah, that's
obviously the one that, you know, if I was writing

(04:20):
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, Jillenhall, 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 stam And I think that's maybe why people

(04:42):
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 to Kennedy. Were you independently interested in Kennedy lore
or was it just a funny, you know, tabloid story.

Speaker 5 (05:01):
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.

Speaker 3 (05:16):
Routes you can go down.

Speaker 5 (05:18):
I didn't, like, specifically have a Kennedy thing, but I
have friends who were 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

(05:40):
up to that point she was very much being managed
versus the manager of her own deal totally.

Speaker 1 (05:48):
Just a little give a little context on who was
Taylor Swift at twenty two years old.

Speaker 5 (05:54):
She's like coming out of her ingenue status. She's pivoting
away from country music. Read is kind of the country
pop hybrid album that eventually cascades into her working with
Jack Antonoff on nineteen eighty nine, which sets forward like
pop Taylor. But this is maybe also the last era

(06:18):
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.

Speaker 3 (06:39):
But the idea that someone would sort of very easily
be able to.

Speaker 5 (06:42):
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 for her friends.

Speaker 3 (06:50):
Who just so happened to be writers.

Speaker 5 (06:51):
But this is the point at which she's making kind
of a legitimacy play as an adult artist and singer
song writer.

Speaker 4 (07:00):
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

(07:21):
to be a major pop star. So the New Yorker
profile is interesting. We had our in our very comprehensive
research dock 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 nine hundred
page book called The Kennedy Women. So what do you
make of her alleged Kennedy obsession.

Speaker 5 (07:42):
I think it's kind of the bridge out of her
country Americana stuff into her pop Americana stuff.

Speaker 3 (07:48):
Like the Kennedy's are so pop music.

Speaker 5 (07:51):
They're hot, they're maybe bisexual, you know, they're catholic. And
when she goes pop at first, she goes into this
it's like fifties, sixties Kennedy esque stripe bathing suit, big
wide brim hat type of thing out of the like
country music, thick strap, tank top guitar vibes. So it's

(08:11):
like the most image friendly ideal for her, and a
latch onto where she doesn't lose her country fans but
is a lot American. She's staying American, just hopping over,
taking a couple steps towards the middle.

Speaker 3 (08:27):
I guess, yeah, absolutely.

Speaker 5 (08:29):
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 nineteen fifties bathing suit, and I
feel like that's when like this part of Taylor comes
to fruition.

Speaker 3 (08:40):
It's like Tumblr Taylor, Yeah it is. It's try. It's
try sugar Cookie era Taylor.

Speaker 5 (08:46):
We're like, yeah, 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 tree Pain says it's okay for her to like
comment on a TikTok.

Speaker 4 (08:59):
See, I didn't even know. 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. That was like a whole era, and she
was like active on it.

Speaker 5 (09:14):
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 tumble her
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.

Speaker 4 (09:27):
I definitely think you could. I guess I had never
made that connection. But to sort of fetishize the Kennedy's
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 Kennedy's, 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,

(09:51):
the way that she gets in contact with the Kennedy's
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 Junior'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 Sport. That's where

(10:14):
she meets Connor Kennedy, who is famously seventeen at the time,
but then turns eighteen three weeks after they meet. Even
though to this day, I guess many more dramatic members
of this fifty community say that she dated.

Speaker 5 (10:25):
A minor of course, Well, with that back to back
with Harry Styles, they were very upset with her.

Speaker 4 (10:30):
At that time, and she's twenty two, we should say
at the time. I think, yeah, So basically she starts
developing some sort of friendship relationship with Connor in twenty twelve.
How is that received in the fandom?

Speaker 5 (10:44):
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 Kennedy's world, there's also
a brief period where it looks like maybe she has
a thing going with Patrick Schwarzenegger, right, who is also
Kennedy in his own way, but that kind of different flavor,
shall we say of Kennedy because of the Arnold Schwarzenegger

(11:05):
of it.

Speaker 3 (11:05):
All, but that winds up not happening.

Speaker 5 (11:08):
I believe this is before he dates Miley then, but
it's interesting to think of the paths diverging.

Speaker 4 (11:13):
Yeah, and he's eighteen at the time, I believe, And
for anyone who doesn't know, his parents are Maria Schreiver
and Arnold Schwarzenegger. And at the time, he was very
much like an aspiring hot actor slash model. There was
no pristige, you know, model slash actor model slash Okay,
so there were rumors about Patrick.

Speaker 3 (11:31):
Rumors about Patrick. I think he's a better actor than model.

Speaker 4 (11:34):
Well now and now we all of course do because
of the white lotus.

Speaker 5 (11:37):
Now, yeah, 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

(11:59):
star persona because of.

Speaker 3 (12:01):
How all in she goes on the Kennedys.

Speaker 5 (12:03):
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.

Speaker 1 (12:22):
Trying to 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.

Speaker 5 (12:40):
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?

Speaker 4 (13:00):
Totally?

Speaker 5 (13:00):
And you see that in the wildly oscillating between Connor
Kennedy and Harry styles versus like John Mayer and Jake Jillenhall.

Speaker 4 (13:07):
Yeah, and I think that you could so easily argue
that the narrative around the Connor 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 expressing her
obsession with the Kennedy family in multiple platforms and then

(13:29):
within months announcing that she is dating someone.

Speaker 1 (13:48):
Okay, the other thing about this a little bit of
exposition before Taylor shows up.

Speaker 3 (13:54):
She meets them all on July fourth, right.

Speaker 1 (13:56):
July fourth, at the Kennedy Compound. 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 seems like not a great idea

(14:17):
for an older person to be approaching them for romantic relationship.

Speaker 4 (14:21):
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 as she didn't show up crazed
and ready to be a predator totally.

Speaker 5 (14:34):
I get the sense that her initial presence is welcome
and a nice distraction, perhaps from all that they have
been dealing with.

Speaker 4 (14:43):
And again they read I mean Ry 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 Kennedy's,
you know, as we as we know, have a long

(15:03):
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 Ethyl and the whole family, and Frank,
can you tell us what Starlight is about?

Speaker 3 (15:21):
Starlight is about Ethyl, of course, and it is.

Speaker 4 (15:24):
A fictionalized account of her love story with Bobby.

Speaker 3 (15:28):
I think loosely fictionalized.

Speaker 5 (15:30):
I think she's pulling from the nine hundred page book
that for the record, I believe she read all of correct. Yeah,
because she's always kind of doing shit like this. But yeah,
she writes the song Starlight from the point of view
of Ethyl and sings it to Ethyl 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.

Speaker 4 (15:52):
Yeah, and somehow it's funny. I was expect cause I
think people I don't know, I'm 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

(16:13):
must have liked it to some extent.

Speaker 5 (16:14):
Yeah, I think that song's fine. I've 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 like special.

Speaker 1 (16:34):
Even 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 do, could you tell us that story.

Speaker 3 (16:47):
They crash they well, they may or may not have
crashed a wedding. I need to pull up who got married.

Speaker 4 (16:53):
It was Liam Kerr and Kyle Kennedy, right, Okay, And
Kyle is Connor's cousin. She's the daughter of Michael Kennedy,
a brother of RFK Junior, who died in a skiing
accident in nineteen ninety seven.

Speaker 5 (17:05):
Right, So they crash 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 eighteen
year old to think about a wedding in his family.
But they show up together and it is seen as

(17:27):
a kind of upstaging of the wedding itself, and Vicki,
who is the mother of the bride, gets pretty pissed
off about this, and and Gab's 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.

Speaker 4 (17:46):
And then Taylor, from what I understand, maintains that she
was invited.

Speaker 3 (17:50):
She more maintains that she never would have crashed.

Speaker 4 (17:53):
Away that she was told she could go.

Speaker 5 (17:55):
She's like, I would not have just like done this,
which also feels correct.

Speaker 3 (17:59):
I think she's not lying yeah about.

Speaker 5 (18:01):
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 back seat

(18:23):
to all of their dramas and romances and stuff like that.

Speaker 1 (18:26):
We do have another person weighing in on the context
later on, which is Kathy Lee Giffert.

Speaker 4 (18:34):
What did Kathy Lee Gifford say?

Speaker 3 (18:35):
She said that they crashed.

Speaker 4 (18:37):
She was like, it was a crash, and she said
that like to the press or on TV. Okay, I
think she said it on TV, and then was that
what sort of got the story going and got everyone
talking about it.

Speaker 5 (18:49):
I believe that is how it okay sort of then
really catches fire.

Speaker 4 (18:53):
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
Harold she said, I responded with a very clear please
do not come. They came anyway. I personally went up
to Miss 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.

(19:16):
She seemed to look right past me, which is so
crazy because the Kennedys are not 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.

Speaker 5 (19:32):
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.

Speaker 3 (19:53):
All anyone ever has to say about her.

Speaker 5 (19:55):
So this both like shatters and perpetuates an image that
she 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.

Speaker 1 (20:10):
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 very same weekend of the wedding,
she and Connor go to visit his mother's grave site
as she is committed suicide just two months earlier.

Speaker 5 (20:28):
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, where I never believe
the paparazzi just happened to be anywhere, let alone say
a cemetery, such that I find this quite craven.

Speaker 4 (20:48):
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.

Speaker 3 (20:59):
That's right, and he's looking very sad.

Speaker 4 (21:02):
And she helped clear some overgrown brush from around the gravestone.
It's like she's really participating in the performance.

Speaker 5 (21:09):
She's in like a little sun dress, her lipstick. She's
in like Taylor Swift costume basically.

Speaker 3 (21:16):
And this isn'ting.

Speaker 1 (21:17):
We'll definitely talk about when we get to RFK Junior.
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 eighty yards away or something. And so

(21:39):
that's why there's overgrown like he put her in an
unmarked grave.

Speaker 4 (21:43):
Why did he do that.

Speaker 1 (21:44):
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 going on, and their eighteen
year old son is dating a twenty two year old

(22:04):
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.

Speaker 4 (22:15):
So to me, the sort of trifecta of controversies with
the Connor 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?

Speaker 5 (22:33):
There's a sort of cul de sac in Massachusetts where
several of the houses in this cul de sac belonged
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.

Speaker 3 (22:54):
She moves in like no joke across the.

Speaker 5 (22:56):
Street from the Kennedy compound 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 flex of
wealth on her behalf that she's, you know, twenty two

(23:20):
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 I mean, the
other thing.

Speaker 1 (23:38):
About Taylor Swift today is like her real estate portfolio
on its own is like rivals.

Speaker 3 (23:47):
People's entire lives are devoted to.

Speaker 4 (23:49):
Yeah, she's a regular Ellen DeGeneres.

Speaker 1 (23:51):
Yeah, 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
looking 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

(24:14):
is when she closes on the house and it's a
four and a half million dollar house.

Speaker 5 (24:19):
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.

Speaker 4 (24:27):
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 Kennedy, 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

(24:47):
has a really happy ending because she actually sold the
house in March of twenty thirteen for five point six
million dollars and collected a nice check from flipping the property.
So all's while it ends, well.

Speaker 5 (24:57):
Yeah, I'm so glad she winds up getting a big
house in Rhode Island. It 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 Lively.

Speaker 1 (25:15):
And Selena Gomez totally, Tom Hidleston and Tom Hddleston.

Speaker 3 (25:19):
I love ts shirts heard. I remember these things.

Speaker 1 (25:22):
I was not, you know, I was following the celebrity
gossip blogs.

Speaker 3 (25:26):
At this time.

Speaker 1 (25:27):
And I think that that is maybe my sole understanding
of Taylor Swift at this period of time for the
next like probably like five.

Speaker 4 (25:34):
Yearsn't 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 friend, I would love your take on this,
which is like intentionally fanning rumors about her love life

(25:54):
and then being defensive about the sort of offensive coverage
of it. So she's like totally 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 eated seven guys in
one year, and then she'll be like, here comes the
sexist media again, trying to make me out to be

(26:14):
this promiscuous like gall 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.

Speaker 5 (26:34):
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

(26:54):
to Giny 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

(27:18):
opportunity to garner a kind of sympathy.

Speaker 1 (27:22):
I thought you were going to say the Tina Fey
Amy Poehler joke where she said there's a special place
in hell for women to 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, right In
sort of her relationship to the media, she proves kind.

Speaker 5 (27:39):
Of over and over again a lack of a sense
of humor. But then when her friends get interviewed, the
Hymes and Lord and Selena Gomezler whoever, they're always like
and Taylor is the funniest person of all time, and
it's like, well, that.

Speaker 3 (27:53):
Can't be true.

Speaker 5 (27:54):
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 you 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

(28:17):
to be actually like reckoning with the parts of herself
that she doesn't like more than blaming other people.

Speaker 3 (28:23):
I mean to be fair.

Speaker 1 (28:25):
To be a fourteen 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, I've never
been there. Maybe it does take that long, but it
is shocking.

Speaker 3 (28:40):
I don't know.

Speaker 1 (28:41):
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.

Speaker 3 (28:56):
Is just kind of shocking to me.

Speaker 4 (28:58):
I know. But it led to the slap, so it's like,
all 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 to close the loop

(29:24):
on Connor though, fran I want you to tell us
how long did this relationship last?

Speaker 3 (29:28):
Two and a half months?

Speaker 4 (29:29):
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 fourth, it sort of lasted through like August,

(29:52):
maybe September, and then apparently she started dating Harry Styles
in December of twenty twelve of that year.

Speaker 5 (29:57):
Yeah, well, because they have the winter romance reflected upon
in nineteen eighty nine, so Rebel that's the cold Weather
album and then read as sort of a summer album.

Speaker 4 (30:07):
Oh interesting.

Speaker 5 (30:08):
This is also I guess like twenty twelve to twenty
sixteen is the last good era of Taylor Swift paparazzi photos,
because there's the gray paparazzi photos with Connor. There's like
when Harry Styles left her on a boat. Her sitting
on the.

Speaker 3 (30:20):
Boat alone is a great photo.

Speaker 5 (30:22):
And then it sort of culminates with like all the
Tom Hidleston 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, but now she'll just
go out to dinner for the rest of her life.

Speaker 3 (30:35):
There's no funny paparazzi photos.

Speaker 4 (30:37):
Yeah, No, it's just via Corona every single night with
Blake Lively and we better be satisfied with what we're getting.

Speaker 3 (30:42):
Yeah.

Speaker 1 (30:43):
And I was standing behind her and Jake Jillenhall 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, it sold it
to the gossip blog.

Speaker 3 (30:56):
Well was there vibe?

Speaker 4 (30:57):
Oh?

Speaker 1 (30:58):
First, I didn't recognize her at all. She just looked
like a regular college girl in Nashville. And this was
really our college coffee shop.

Speaker 3 (31:05):
And I know it's Jake Jillenhall because he's Jake jillen Hall.

Speaker 1 (31:07):
Also, I'm just realizing that my other celebrity sting at
that coffee shop was cursed and dunst.

Speaker 3 (31:12):
Wow, now there's a Miss Americana.

Speaker 4 (31:15):
I know. I got to visit that coffee shop. And
actually there's another person that dated Jake jill in Hall.

Speaker 1 (31:19):
Yeah, that's what I was saying, Like, it's like, well,
you know, they have a lot of things in common.

Speaker 3 (31:24):
This is so besides the point.

Speaker 5 (31:25):
But my friend Doo teaches high school, took his students
to see the Denzel Washington Jake jilln hall Othello, because
there were like the student tickets. And I was like,
do your high school students like know who Jake Jillen
Hall is? And he was like, no, they have no
idea who this is, Like he's not famous to them.

Speaker 3 (31:39):
I was like, that's crazy.

Speaker 4 (31:40):
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. Absolutely, I do want to say, you know,
talking about all these people again. In twenty thirteen in
Vanity Fair, Taylor basically said I've dated exactly two people
since twenty ten, meaning Connor Kennedy and Harry Styles. So

(32:03):
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 ones, and she thinks it's
offensive that there are these carousels with her with various
men because she only needed two people between twenty ten
and twenty thirteen.

Speaker 5 (32:17):
I do think the culture was much meaner about her
having a multiple boyfriends. I think if she was a
sort of Sabrina carpenterish 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 celebrities

(32:37):
get frozen in the time in which they become famous,
and which is why there is always perpetually kind of
cringe twenty tennis to her. That makes people a specific
kind of insane.

Speaker 4 (32:47):
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 Antihero?
Anti Hero? Yeah, and the humor 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 twenty tens millennial Blurg you

(33:11):
know has rewatched you know, the Office in thirty rock.
And I'm in no way implying thirty rock as cringe.
It is literally my favorite comedy on television, but it
is you know, the references are sort of like twenty
tens 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

(33:31):
sort of all her references are dated, even her album covers.
The aesthetics of them are always like one sort of
three year period too late, like that nineteen eighty nine
is this like polaroid photo that was already washed at
the time. That's like hipstomatic prints.

Speaker 5 (33:45):
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 mind just
an old woman deep down, and.

Speaker 3 (33:57):
That's where I'm like, yeah, you are exactly.

Speaker 4 (33:59):
Even her thing about being a cat lady, like she's
that's another kind of like millennial tinged trope.

Speaker 5 (34:06):
Yeah, Like, there's a lot of pop stars and I
think celebrities who are just gonna be feeling like the
Long Tale of Bratt, where Bratt 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.

Speaker 4 (34:25):
I do want to see. The closest she's gotten to
Brett is Reputation, which is my favorite era, and you know,
she's no Charlie xx, but some of those songs really
really still slap.

Speaker 3 (34:33):
Yeah.

Speaker 5 (34:33):
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.

Speaker 3 (34:43):
Yes. The one thing I wanted to add that we missed.

Speaker 1 (34:45):
Ethel Kennedy is asked, do you think they're going to
get married?

Speaker 3 (34:50):
As we know in so many words?

Speaker 1 (34:52):
And Ethel Kennedy says, we would be so lucky, which
is a it's, you know, a very nice thing to say.
So we're talking about children here. Basically, 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.

Speaker 3 (35:10):
Maybe they're Catholics, like that's when they started thinking about that.

Speaker 4 (35:14):
Yeah, no, they're like the clack 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.

(35:35):
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
Kennedy's right sort of.

Speaker 5 (35:49):
Okay, is 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

(36:11):
like ethel or I don't know, JK.

Speaker 3 (36:14):
Junior or anything like that.

Speaker 5 (36:15):
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 air to a lot of money,
but the one to ones with Kennedy's like, don't really
got line up. I think she's just sort of conceptually
taking the idea of American dynasty, which she got from
the Kennedy's and reapplying it.

Speaker 3 (36:34):
But so much of that album is a kind of
like auto fiction.

Speaker 4 (36:38):
Project, 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 Hyanna support and wreaking havoc or
even crashing the wedding or whatever.

Speaker 5 (36:53):
Yeah, I think it's sort of drawing from like all
this stuff that era to me always feels like because
she's like deep in the Joe all In 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.

Speaker 4 (37:12):
Before we end, I do want to say, friend, you
I think are the person that told me Connor Kennedy
went to fight in Ukraine.

Speaker 5 (37:19):
That's right, that's the last I heard about him, because
I had felt and this is like not so so recent.
I believe it was twenty twenty two, Yes, where I
feel like none of us had heard about him post
Taylor Swift breakup.

Speaker 3 (37:33):
That's fine.

Speaker 5 (37:33):
Maybe he wants to be as much of a civilian
as a Kennedy can be a civilian. But he sort
of re emerges in fall of twenty twenty two 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.

(37:55):
He didn't tell people they are like who he was
related to, and how he felt like it was a
cause he.

Speaker 3 (38:01):
Really had to get behind.

Speaker 5 (38:04):
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. Wow, And now
he's just like engaged and Backstateside.

Speaker 3 (38:17):
Yeah to a singer songwriter.

Speaker 4 (38:18):
Yes, a Brazilian singer songwriter, Julia b.

Speaker 1 (38:21):
We might be seeing him on the ballot someday.

Speaker 4 (38:23):
Yeah, he is really the dark horse of the Kennedy's
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.

Speaker 1 (38:41):
I mean, that's quite a bit more experience in politics
than Vogue's political consultant for four weeks.

Speaker 4 (38:49):
Yes, exactly. All right, So well, I just want to
say we hear 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 to Taylor's version.

Speaker 3 (39:08):
It's good, It's really good. It's the best Taylor's version.
I think.

Speaker 4 (39:11):
There you have it. All right, thanks so much for
v Thank you.

Speaker 3 (39:15):
That's it for this week's episode.

Speaker 4 (39:16):
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 Junior, and the heyday of
George Magazine.

Speaker 1 (39:27):
So subscribe and follow United States of Kennedy for all
things Kennedy every week
Advertise With Us

Popular Podcasts

Stuff You Should Know
New Heights with Jason & Travis Kelce

New Heights with Jason & Travis Kelce

Football’s funniest family duo — Jason Kelce of the Philadelphia Eagles and Travis Kelce of the Kansas City Chiefs — team up to provide next-level access to life in the league as it unfolds. The two brothers and Super Bowl champions drop weekly insights about the weekly slate of games and share their INSIDE perspectives on trending NFL news and sports headlines. They also endlessly rag on each other as brothers do, chat the latest in pop culture and welcome some very popular and well-known friends to chat with them. Check out new episodes every Wednesday. Follow New Heights on the Wondery App, YouTube or wherever you get your podcasts. You can listen to new episodes early and ad-free, and get exclusive content on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. And join our new membership for a unique fan experience by going to the New Heights YouTube channel now!

24/7 News: The Latest

24/7 News: The Latest

The latest news in 4 minutes updated every hour, every day.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.