Revisiting The Great American Romance of JFK Jr. & Carolyn Bessette

Summary

Pop Apologists Podcast: "Revisiting The Great American Romance of JFK Jr. & Carolyn Bessette"

Released on December 25, 2024, "Pop Apologists" by PodcastOne delves into the captivating and tragic love story of JFK Jr. and Carolyn Bessette Kennedy. Hosted by sisters Lauren (A) and Chandler (B), this episode offers a detailed exploration of their iconic relationship, blending rich historical context with engaging personal insights.

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1. Introduction and Setting the Scene

Lauren opens the episode by explaining the intent to pivot from current events to a deep dive into a culturally significant couple. She states, “We are going to be chatting about the romance, the lives, the human beings, the sordid tales, the drama, the gossip, everything that you want to know about JFK Jr. And Carolyn Bessette Kennedy” (A: 01:18).

Chandler expresses relief in stepping back from heavy current topics like Roe v. Wade, appreciating the opportunity to explore a classic love story instead (B: 00:28).

2. Charm and Enigma of JFK Jr. & Carolyn Bessette

The hosts discuss the allure of JFK Jr. and Carolyn, highlighting their enigmatic personas compared to today's oversaturated celebrity culture. Lauren mentions, “People like JFK Jr. and Carolyn Bessette, they really were enigmas because they gave Carolyn gave no public interviews. JFK Jr. gave very few” (A: 04:40). This scarcity of public exposure made them more compelling figures.

Chandler contrasts the polished image of past celebrities with today’s more openly flawed personalities, noting a sense of nostalgia for the “veneer of polish” that was present before (B: 03:39).

3. The Meeting and Building the Relationship

Carolyn Bessette, born in 1966 in White Plains, New York, was an elegant and influential figure in the fashion world, serving as Calvin Klein’s Director of Publicity. A pivotal moment was her joining Calvin Klein, where she became a muse and significantly influenced the brand’s image (A: 22:46).

Their meeting is shrouded in romantic lore, with rumors suggesting they met at a Calvin Klein event in 1994, where Geoffrey met Carolyn by chance and exchange of numbers (A: 26:21). Their relationship blossomed despite prior entanglements with other high-profile figures like Daryl Hannah, whom JFK Jr. dated before Carolyn.

4. Navigating the Kennedy Family and Wedding Preparations

The episode delves into the inherent challenges Carolyn faced when integrating into the storied Kennedy family. Lauren recounts Carolyn's first awkward interactions, such as her delayed response in standing when Ethel Kennedy entered a room, causing significant strain (A: 33:04).

Despite these challenges, John (JFK Jr.) and Carolyn's relationship deepened, culminating in a secretive and intimate wedding. Lauren highlights the couple's desire for privacy amid their high-profile lives, orchestrating a clandestine ceremony on Cumberland Island, Georgia, with only 40 guests (A: 48:54).

5. The Iconic Wedding

Their wedding was a blend of simplicity and elegance, reflective of Carolyn’s minimalist style and the couple’s desire to escape the constant public gaze. Chandler describes the event as, “a stunning candlelit wedding” where logistics like a dress malfunction only added to the memorable and intimate atmosphere (B: 51:57).

Notably, Carolyn’s dress by Narciso Rodriguez broke the mold of the era’s ball gowns, introducing a bold, sleek silhouette that became iconic (B: 54:25).

6. Struggles in Marriage

Post-wedding, the couple faced mounting pressures from both their demanding careers and the Kennedy legacy. Lauren explains how JFK Jr.’s dedication to George magazine and frequent family obligations left Carolyn feeling isolated and lonely (A: 58:19).

The hosts recount various marital fights, often captured by paparazzi, highlighting the strain of balancing personal happiness with public expectations. A particularly intense argument at Washington Square Park exemplifies their growing disconnect (A: 42:47).

7. The Downward Spiral and the Tragic Crash

By 1998, Carolyn’s struggles became evident, with reports of heavy cocaine use and emotional distress. Lauren narrates how Carolyn’s loneliness and JFK Jr.’s absence led to an emotional affair with a close friend, further destabilizing their marriage (B: 60:02).

The episode meticulously details the factors leading up to the tragic plane crash in 1999. JFK Jr.'s inadequate pilot training, disregard for weather briefings, and the physiological effects of vertigo culminated in the fatal accident near Martha’s Vineyard. Lauren poignantly reflects, “I cannot even imagine the final, you know, their final terrifying moments as they plunged into the sea” (A: 69:41).

8. Reflections and Conclusion

Lauren and Chandler conclude by pondering the inevitability of the couple's struggles and the profound impact of their untimely death on American pop culture. They emphasize the lessons learned about the pressures of high-profile relationships and the importance of personal well-being over public expectations.

Chandler humorously suggests future episodes focusing on other iconic couples, while Lauren expresses a desire to continue offering deep, narrative-driven content (A: 72:09).

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Notable Quotes with Timestamps

• Lauren (A):

  • “We are going to be chatting about the romance, the lives, the human beings, the sordid tales, the drama, the gossip, everything that you want to know about JFK Jr. And Carolyn Bessette Kennedy” (01:18)
  • “People like JFK Jr. and Carolyn Bessette, they really were enigmas because they gave Carolyn gave no public interviews. JFK Jr. gave very few” (04:40)
  • “I cannot even imagine the final, you know, their final terrifying moments as they plunged into the sea” (69:41)

• Chandler (B):

  • “Oh, really? Really? That's how you want to get this started? Actually, I appreciate that it's better than the well, well, well, that I'm well, well, well, pretty sick of.” (00:04)
  • “Please forgive me, but I think that really, Carolyn Bassett, she wasn't a movie star...she was a normal girl from a normal family.” (21:55)
  • “Weapons ban. That's great. That's great.” (72:28)

Conclusion

This episode of "Pop Apologists" offers an intimate and comprehensive look into the lives of JFK Jr. and Carolyn Bessette Kennedy. Through engaging dialogue, the hosts unravel the complexities of their relationship, the pressures of fame, and the tragic circumstances that led to their untimely deaths. Rich with anecdotes and reflective insights, the episode serves both as a tribute and a cautionary tale about love under the relentless gaze of the public eye.

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Note: Timestamps correspond to points in the provided transcript to facilitate easy reference.

Transcript

[A]

Hello, loser.

[B]

Oh, really? Really? That's how you want to get this started? Actually, I appreciate that it's better than the well, well, well, that I'm well, well, well, pretty sick of.

[A]

Oh my gosh, Chandler. Today is an interesting day recording the pod because lots going on but we are taking a little bit of a left turn from current events.

[B]

I'm actually, I'm happy to go back in time. Today feels like a very heavy day with like the Roe v. Wade stuff that we woke up to. The Met gala looks, a lot of them were a big fat let down to me. So I'm happy to go back in time today. Lauren?

[A]

Yeah, I had this idea a few weeks ago. I thought let's, I think maybe once a month let's do an episode that's just like basically telling the story, doing a deep dive into a couple or a person or an event. Something that has a lot of public interest. So this is the first in a series of essentially pop apologists covering icons and today we're covering an iconic couple.

[B]

So we are very, very excited because.

[A]

We are going to be chatting. The romance, the lives, the human beings, the sordid tales, the drama, the goss, everything that you want to know about JFK Jr. And Carolyn Bessette Kennedy.

[B]

Correct.

[A]

And you know, it's interesting because as I was reviewing all of the research for today, I just really loved reading about it.

[B]

Like, yeah, it's fascinating. It's, it's fascinating to like not only is their love story almost out of a fairy tale, but I think the history with JFK Jr. And how he was, you know, the, the boy saluting his father's casket, like there's just the history is so rich. And he was also really hot, which makes it very interesting to learn about.

[A]

Well, frankly, that was actually one of my first go to instincts as I was researching all of this was.

[B]

Yeah, I was really just kind of.

[A]

Taken aback by how much our country used to be blessed with very attractive politicians. Like hot presidents. Hot presidents.

[B]

I mean, who else besides JFK Jr. I mean, who else besides JFK, JFK?

[A]

I mean people would argue that like Orson Welles. Oh yeah, Obama's Lincoln. I'm a huge.

[B]

I don't know if Orson Welles was a, was a prophet or was of the Mormon church or if he was an American president because I get those two. I get all those white guy names mixed up all the time.

[A]

I have no idea who Orson Welles is, but Lincoln is super.

[B]

Maybe he's an author.

[A]

Anyways, I think that yeah, there was A moment in time where politicians and.

[B]

Hold on.

[A]

What?

[B]

Can I offer a redaction. Orson Welles was an American director. I don't have my shit straight.

[A]

Excuse me?

[B]

I don't have my shit straight for this. I don't know where I came up with. Orson Welles was an American president, but. Sorry about that, everybody. Historians out there. Apologies. I'm not great at geography or American history, clearly. So anyways.

[A]

Clearly. Okay. Glad you cleared that up. Glad you issued that reduction redaction. Anyway. Yeah, I just think that it was just. How do you even describe it? I think that celebrities, on some level, and although all the public figures that we used to care about there used. There was just a veneer of polish.

[B]

Yes.

[A]

That is absent today.

[B]

Oh, absolutely. I think that our celebrities are much more morally bankrupt and. And maybe all of these celebrities, all these icons have always been morally bankrupt, but they just weren't allowed to show it. And I think that maybe that was toxic at their time because they felt so much pressure to, you know, have that veneer or shine. But sometimes I miss it.

[A]

No.

[B]

For example, let's bring back the toxicity. In my opinion, Pete Davidson, I'm not super interested in him being, like, the icon and celebrity of my time, frankly.

[A]

Well, okay. And here's. Here's really where I think the intrigue comes in. I mean, we're in such a different time where we are saturated with celebrity content. We see what they ate for lunch. We see them all the time over social media. But people like JFK Jr. Like Carolyn Bessette, they really were enigmas because they gave. Ve. Carolyn gave no public interviews. JFK Jr. Gave very few. And really, they were much more compelling.

[B]

Characters because, well, I think, like, didn't.

[A]

Know much about them, and.

[B]

And I think there's a dynamic for. That has. I think there's a dynamic that has shifted where before, celebrities were, you know, hid from the public, were extremely private at all costs, you know, did not want any dirty laundry aired. And now it's like, the more dirty laundry you air, the more, like, you can garner an audience or, you know, kind of, like, win people over. And it's. And I don't. I don't know. I don't really know that I actually prefer one or the other because I. I like knowing what salad Kim Kardashian ate.

[A]

Yeah. I like the additional content. And I find myself disinterested in celebrities who are not playing, like, the new game. Like a Beyonce, for example.

[B]

Beyonce?

[A]

Yeah. Like, yeah, I get that she's way more talented than a Lot of celebrities that are much more notorious these days or get a lot more pr, But I also find myself vaguely, you know, not that interested.

[B]

Totally. No, it's really fascinating because I feel like we're even contradicting ourselves. Like, we want it, but we also don't.

[A]

Yeah, well, anyway, you know, do we contradict ourselves? Very well then we contradict ourselves. Let's. Very well, then let's move on to JFK Jr. And Carolyn Bessette Kennedy. Because for me, I had always known that they were this com. You know, completely iconic American royalty couple. Super gorgeous. Obviously she's an absolute style icon, but I didn't really know much else and kind of just want to talk about her style to begin with before we get into the narrative and.

[B]

Okay.

[A]

Where they started. What I think is interesting about her style is that really everything that she wears is so simple and nothing in and of itself is remarkable, but put together, she really looks just iconically beautiful. And Maybe it is that 90s classic style that, you know, Gwyneth Paltrow, Kate Moss, they were all kind of famous for.

[B]

Yeah.

[A]

But there's just something about it. Like, if I put on, you know, boot cut khaki pants and a white tank top, I guarantee you I would not have the same level of sophistication and it would not be nearly as distinctive.

[B]

Even her hair is never overly done. Like, it's always like the effortless day two hair.

[A]

Yes. And that the effortless day two hair is seriously impossible for me to accomplish. I will also say, though, that the thing that I love about her is how incredibly natural her face looks like. I think Carolyn Bissette Kennedy is a great example to all of us to remember that natural faces, faces with some flaws, faces that from some angles don't look perfect, really have a level of intrigue to them and have a level of, I think, ease to them on some level. Like, it's just so. They're so beautiful and natural looking. And it's just a good reminder in the age of tweaking ourselves into Instagram perfection.

[B]

Right, right. Absolutely. Yeah. So anyway, also, might I add one more thing? I'll add, I think also she looks amazing when she's standing next to a very hot guy like JFK Jr. Like, they. They're such a hot couple with their coloring. Like, dark, handsome, her, you know, bright blonde. Like, everyone's gonna be like, hey, you only like blondes. But, like, she looks like a hot blonde and he's like a hot dog dark haired guy. Like, it's like Barbie and Ken kind of. It's. It's hot. I'm gonna say it.

[A]

Absolutely. I think that the platinum hair, actually, I think that was probably the key ingredient that allowed her to have a subdued look virtually everywh. And.

[B]

Right.

[A]

Come across as looking completely iconic at all times.

[B]

Right. Maybe that's where mom was going with our, you know, continual efforts to be blonder and blonder.

[A]

Yeah, well, American royalty vibes. If only.

[B]

If only we were a far cry from American royalty, I'll be honest. But.

[A]

Okay, moving on. I think that we should get into the topic at hand. Carolyn Bessette Kennedy and JFK Jr. How they met, who they were, and the story behind the iconic couple. Are you ready? Yes.

[B]

Let's do it, please.

[A]

Okay. This is really quintessentially a 90s love story of two people caught between two worlds, the life they were trying to build together as husband and wife, and what the public and the Kennedy family wanted out of them. Because, as you. As we all know, the Kennedy family is really as close as the US has come to having a royal family.

[B]

Yes.

[A]

JFK Jr was in the spotlight his entire life. He. Okay. When he was born, his birth announcement was on the COVID of the New York Times above the fold.

[B]

I mean, he was America's crown prince.

[A]

I've heard. Yes, yes. And. And I think that to this day, we don't have anyone who.

[B]

Barron Trump. Not Barron Trump.

[A]

You know, Malia Obama. I mean, they're all cute. I mean, don't have a classic American prince.

[B]

Right. JFK Jr. Would have never gone to Coachella.

[A]

Absolutely not. Okay, so apparently this. I love this fact. Jackie O. Jackie Onassis Kennedy.

[B]

Yeah.

[A]

Was really kind of a stage mom, if you will. She really was aggressive in wanting JFK Jr. To continue into the tradition of the Kennedy family, of the men doing the men, especially doing important, serious, respectable work. She did not want to see any sort of tomfoolery. She only wanted to see prestige and academic accomplishment.

[B]

I mean, I think a lot was expected of her as she raised these two kids by herself after JFK passed away, or, you know, was tragically, you know, like, I think that she was. She married into the Kennedy family. And I'm sure that a ton of pressure also came from that side of the family, too, that, you know, she was just left now to navigate that by herself.

[A]

Yeah, that's a. That's a very good point. Well, so in an effort to have him live up to his family name, Jackie sends him to boarding school while he's at high school because he's just not, he's not performing well and she feels like he's goofing off too much.

[B]

Okay.

[A]

Apparently he was only getting average great or he was not getting good grades.

[B]

Okay.

[A]

So she sends him to boarding school and he. And from there he only gets average, average grades and he's diagnosed with ADD and put on Ritalin. This didn't help. He still flunked the 11th grade. But as one does, I'm sure the Kennedy name helped. She did not need to photoshop him onto a picture in the rowing team because he was able to still get into an Ivy League school. But while at school he was put on academic probation. So Jackie would write letters to his professors, you know, apologizing, saying that he was going to do well and she was going to personally see to it that she, that he was going to do well. And interestingly enough though, he really excelled at the theater and loved acting and drama. However, she did not approve of his love of acting and she told him that she would disinherit him if he didn't quit his silly dreams and get serious about his future.

[B]

I mean, that is one tough cookie. It's kind of like also, did everybody need to become politicians from that family? Like, didn't we have enough?

[A]

Interesting. I think it's also interesting that him being a movie star wouldn't be enough. I mean, really, can you imagine, you have this son, he literally looks like a Greek God, you know, descended from heaven to bless us all with his beauty. And he also has. Loves acting and I guess, you know, being the next Cary Grant isn't good enough for Miss Jackie. Oh, he's got to continue in the presidential lineage. I don't know. For me I would be, I just want, I want the, the gods above to know that if I'm send a child with a similar level of hotness and acting ability, I will, I will nurture his God given talent and like.

[B]

You know, I don't know, both. It's interesting that she wanted him to pursue an academic or a political career because I, I just feel like if I were her, I would have wanted to have to get away from that as much as possible and I wouldn't want to be thrust back into that spotlight again.

[A]

Right. Yeah. No, I think that, I think that this is what's interesting. We've kind of talked about, you know, we look at people that are super successful but they, they have like, they have, they live on a height that's really far to fall from and they want their Children to also achieve the same level of success and notoriety that they have achieved most often. Like most of the time, these super successful people, they don't want their kids to go live normal lives. They want their kids to be stars too. And so they, they live under a lot of pressure.

[B]

Yeah.

[A]

But okay, moving on. So John was crowned people set sexiest man alive in 1988. This issue of the magazine sold the most copies that it's ever sold today.

[B]

Wow.

[A]

Which is pretty phenomenal. And Jackie was not happy about this. She thought it would distract from his career path. But John was totally into being a sex symbol. And he even showed up to a big Hollywood Halloween party wearing nothing but a fig leaf.

[B]

Wow.

[A]

Yeah.

[B]

So he knew he was hot.

[A]

Yeah. Oh my gosh. Yes. And he, yeah, he totally leaned into that. He eventually does go to law school though, under the behest of his mother. And he graduates in 1999. To celebrate, he takes out a 46 foot yacht and sails the lake in Virginia. I just like, did the founders of J. Crew, like, did they imagine him? Is this really like the he every.

[B]

He's out of a polo rugby dream catalog.

[A]

Absolutely. He brought along his new girlfriend, the stepdaughter of a billionaire that his uncle Ted set him up with. Won Daryl Hannah. She was a movie star at the time. Completely stunning. He also goes on to date Sarah Jessica Parker, Madonna and Cindy Crawford. Insane at Ameca Insurance. We know it's more than just a car. It's the two door coupe that was there for your first drive. The hatchback that took you cross country in back, and the minivan that tackles the weekly carpool for the cars you couldn't live without. Trust amica Auto insurance. Amica. Empathy is our best policy. So John takes the bar exam. And this is everyone, of course. Just remember he's living a highly public life. Like even though he's a private person, he's being watched by the world.

[B]

And he takes the bar.

[A]

Yeah, for sure. And he takes the bar exam in flunks and you know, the, the New York Post. It's all over the Post. The hunk flunks. It's all over the media. And he's super humiliate, humiliated. Not to mention his sister Caroline passes the bar on the first try.

[B]

Classic.

[A]

Yeah. So he took it again in 1990. Fails again. Even though he, I guess, used a test prep class for that one. And you know, headlines fly. The hunk flunks again.

[B]

Also, can I just say. Yeah, I love like, I love New York Post headlines. Like the hunk flunks again.

[A]

Again.

[B]

It's just. It's so good. It's such, like, camp. I don't know. I love it.

[A]

Jackie insisted that he continue and try again. So she hires him a private tutor. And then Chandler, this is really interesting. She petitions the bar administration to allow him to take a. Take the bar exam in a private room. This was a really big deal because you really should only be allowed to have this, like, special arrangement if you have, I guess, like, some serious issues, serious medical conditions, but hard to say no to Jackie. He was allowed to take it in the private room. And third time was a charm. He finally passed the bar.

[B]

Oh, my gosh. I wonder what the headline was then.

[A]

Well, let's just say that the legal profession in the world at large was very happy about this because he was a natural in the courtroom. He was handsome and charming and friendly. So much so that defendants were constantly confessing things to him. People would literally turn to him as they were led away in handcuffs and say, thanks, it was so nice meeting you. Like, he was literally of the prosecutor, and defendants adored him.

[B]

That is so real. Honestly, people are suckers for a hot guy. People are suckers for a hot guy.

[A]

It's true. So John quits his job, though, at the Prosecutor's office in 1994, because he just said he. This is what he said. It's a nautical metaphor. So let's move with it. He says he felt like he was a passenger on an ocean liner when he wanted to be the captain.

[B]

Okay.

[A]

So he grows. He. He expresses his newfound freedom with growing some facial hair. He grows a goatee and forms an.

[B]

I don't like goatee. JFK Jr. For the record.

[A]

Yeah, it's his least hot look, for sure. He grows a goatee and forms a company with an old friend, Michael Berman. It's called Random Ventures. The goal, Their goal. I mean, I'm really shocked. This company wasn't successful, but their goal was to mass produce handmade kayaks.

[B]

Oh, perfect.

[A]

Doesn't exactly. Scalable. Yeah, exactly.

[B]

Okay. Michael Berman. I didn't really start at the company with Michael Berman.

[A]

Do you know who that is?

[B]

I do. Ding, ding, ding. Everyone keep that in mind for later on.

[A]

Okay? So John then moves on from that failed business and pitches his idea for a magazine to a mix of political and celebrity investors. The magazine would be part serious party reverent, and Jackie apparently tried to talk him out of it. This was not hoity toity enough for the Kennedy name, of course. However, he doesn't Listen to her. And creates George magazine. Apparently one of his biggest supporters at the time was his blonde haired flame, Daryl Hannah. Just a side note, Jackie was never a huge fan of John and Daryl. And I think that's probably because of Daryl's like hippie, Lucy goosey aesthetic. Doesn't really match the button up, buttoned up Kennedy look, you know. Okay, so this is interesting. Around this time In May of 1994, Jackie passes away and before her death. This is a strange premonition, but before her death, Jackie made Maurice Templeman, her longtime companion, promise that John would never fly an airplane. Is that interesting?

[B]

Yeah, it's. Well, I mean, I think she knew about the Kennedy curse, right? Yeah. Wasn't that still a thing before even this happened?

[A]

It was a thing. Yeah. There has been a lot of tragedies in the family. Yeah. Yes. John's brother, who his dad had said he thought would become pre. The next President of the United. Or not JFK Jr's brother, but his father, JFK's brother, who his dad had thought would become President of the United States.

[B]

Bobby. Right.

[A]

I don't know. What? No, I. I think it was. No, no, it was someone else. It was someone. Okay. It was, I think the oldest son, anyway. He died in World War II.

[B]

Oh, right, right, right. Okay. The one. Yeah, like you said, the one who they thought was going to be.

[A]

Yeah, yeah.

[B]

Okay.

[A]

So anyway, another interesting fact about John is that he had the system. The system was arriving 15 minutes late wherever he went. That way whoever he was meeting would always already be there. That way he would not have to sit alone in public because apparently people would rush to him and start talking to him if. Yeah, Another. Other people he dated included Madonna, Cindy Crawford, Sarah Jessica Parker. And at one point when he starts to date Carolyn, they briefly like break up so he can date Daryl Hannah again. But that goes down in flames in June 1994. Yeah, in June of 1994, John and Carolyn start dating exclusively.

[B]

So interesting note about timing here. So only a month after his mom passes away exclusively. I wonder if Jackie ever knew Carolyn.

[A]

And also if they ever met. I don't think. I don't believe they did.

[B]

John is JFK Jr. John, you know, is in the stages and the throws of grief when him and Carolyn start exclusively dating. That's interesting.

[A]

Yeah. I think that. Honestly, everything I'm about to say is total speculation.

[B]

So. Okay.

[A]

Yeah. Forgive me, but I think that really, Carolyn Bassett, she wasn't a movie star. She wasn't. She wasn't Madonna, Cindy Crawford. Sjp or Daryl Hannah, all icons of the time. She literally was a normal girl from a normal family. But I think she had a level of strength and personal fortitude and maybe even lack of vanity and ego at certain down to earthness, Something Kagan was very attracted to. About me. Sure.

[B]

Oh, my gosh.

[A]

And. And no. And I think that really, like, she was just a really solid person, and I think she became really this stable center for him, at least at the beginning.

[B]

Yeah.

[A]

Though she. Her mental state really unravels during their marriage. But we'll get to that in a bit.

[B]

Okay.

[A]

Okay. So should we dive into who Carolyn Bessette is? Chandler?

[B]

Yes, please, please.

[A]

Okay. So Carolyn Bessette was born in 1966 in New York's White Plains. Her father is the engineer William J. Bessette. He's just. He's just an engineer. He's notable engineer. And his. Her mother was Anne Messina, an administrator in New York.

[B]

Do you know any notable engineers? Just asking for a friend.

[A]

Well, I mean, he wasn't like Einstein, you know, or what's who did the light bulb. Thomas Edison. He wasn't like a notable engineer.

[B]

Okay. Okay.

[A]

And her mother was Anne Messina, an administrator in the New York City public school system. So she has two older sisters, twins Lauren and Lisa. So Carolyn lived in upper middle class, traditional, normal life. She receives a degree in elementary education from Boston College. Okay. So apparently at one point, she walked into the Boston Calvin Klein store and was hired on the spot. This is so interesting. So she was so elegant and outgoing that the store manager noticed and immediately promoted her to New York. So she moves to New York, where she essentially is like this ambassador to the brand's VIP clients. And she was eventually promoted to the director of publicity for the company's flagship store in Manhattan. So she kind of becomes the local face of Calvin Klein.

[B]

Right.

[A]

Can you imagine being so incredibly bewitching, like incredible, just. And like, so iconic that you just apply for a job at Calvin Klein and they're like, actually, we want you in New York and we want you to be the first face of the brand.

[B]

Nope. Never. Never even come close to feeling that. That iconic.

[A]

No. Carolyn becomes one of Calvin Klein's muses. And apparently it said that the quote was, every time you design something, think of Carolyn Basset. That's what was told to the Calvin Klein designers. She was also instrumental in Kate Moss. In Kate Moss's success.

[B]

Okay.

[A]

And, yeah, and apparently Anna Wintour compared her popularity with Princess Diana, saying that she had a fabulous modern style. So Carolyn was just one of these women that truly understood how fashion worked, had an instinctual, natural sense of style, and was captivating to people around her.

[B]

Absolutely.

[A]

She was apparently different from the typical gorgeous girls around Manhattan at the time. She didn't have the vibe that she was trying too hard. She was just completely natural and effortless. Also, something interesting about her is that she was not thirsty, so she never craved the spotlight. She, in fact, actively avoided it when she got the spotlight by dating John. She never gave any public interviews. She never created a podcast. She was just.

[B]

Well, yeah, she was just simply normal. I think also that's what makes this story so captivating, is that it's a true Cinderella type of story, right?

[A]

Absolutely. Absolutely. So there's a lot of. There's a lot of tales on how they met. There's nothing confirmed. There's a theory that they met at an event in 1994 and for Calvin Klein. And it was. It was said that she played hard to get, and that drove John crazy because he was literally like the American prince. Apparently went by Deb's rules. Yeah, exactly. Another rumor was that they met while he was shopping at Calvin Klein. The rumor is that he bought. He left the store with three suits, six shirts, a bunch of ties, and Carolyn's number. So that's a little meet cute rumor for y'all.

[B]

Love it.

[A]

Okay, so around. So around 1994, they start dating. They are not exclusive, as we said at the beginning, as we said earlier. And because he's also dating Daryl Hannah at the time, apparently this crushed Carolyn. And at one point, her mom writes to her and says, carolyn, get on with your life, Mom. So I thought that was kind of funny. Some tough love. Very Deb. So, what, Chandler? What finally ends things between John and Daryl? Well, let's just say it was a fateful, fateful, untimely end for Daryl's dog.

[B]

Oh, my gosh. The Kennedy curse even applies to animals.

[A]

So John took Daryl's dog for a walk in NYC and accidentally dropped the leash. The dog apparently ran into traffic, got hit by a car, and died. Daryl.

[B]

Yeah.

[A]

Daryl was devastated and insisted that John get the dog cremated and personally fly the remains to la, where she was going to hold a funeral for the dog. And this, I guess, was the opposite of what John wanted to do. He wanted to do especially while his mom was in extremely poor health. So John sends the dog's ashes in a plain wooden box. And this is just the nail in the coffin for Daryl. She's infuriated, and she dumps John, she. The fact that he did not send the dog's ashes and something more impressive was.

[B]

I mean, you would think that JFK Jr. Could spring for a nice vase or something, but guess not.

[A]

He's just not a dog guy. Okay?

[B]

Apparently not. That's very sad. Also crazy that she dumped him. Do you know that Daryl Hannah was in Forrest Gump?

[A]

Of course I knew Daryl Hannah was in force.

[B]

I didn't know who Daryl Hannah was.

[A]

No. Yeah, of course.

[B]

And she had a kid with Neil Young. This is shocking.

[A]

So after the tragic perishing of the canine and the wooden box faux pas, John and Carolyn start dating exclusively. Okay. And by June, a month after his mother's death, he starts telling his close friends about her. They spend the summer of 1994 together. And by the end of the summer, he wants to introduce her to his family. The Kennedy family. The storied Kennedy family. Carolyn, apparently more than anyone. John, who John had been with. This is a quote from one of his friends, said that she would stand up to him and confront him. And John knew he needed that.

[B]

Okay. Okay.

[A]

Yeah.

[B]

Okay. Love that.

[A]

So the next tale is very, very interesting. It's all about her meeting the Kennedys.

[B]

I just have to say, at the top. Yeah, I am someone who gets stress bowel movements around, like, situations like this. In fact, I, like, wasn't allowed to be dating when I was, like, 15, and I. Every time I would encounter my boyfriend's parents, my, like, secret boyfriend's parents, I would get, like, stress bowel movements. I'll leave it at that. So all that is to say that I cannot even imagine how stressful this would have been.

[A]

Oh, really? See, I'm always quite confident meeting parents.

[B]

Like, I mean, I, like, I'm definitely more confident now, but it. I mean, the first time I met Ben's parents, I was totally, like, not, like, stressed, but super nervous.

[A]

I mean, the thing is, is, like, I'm confident meeting people's parents, but only because I feel confident around normal people. Like, if I was me, if I was getting engaged to Barack Obama's son or something, let me just say, like, some fictional son, I would be terrified. Like, can you imagine some, like, trashy pop apologist hoe like, with basically no esteemed accomplishments walking in? Oh, my gosh.

[B]

Oh, no, that. See that you'd be sent home before, you know, dinner was even served, so.

[A]

Absolutely. And so I think that probably played into it. She's from a normal background. She was working for Calvin Klein, you know, npr. She did not have some crazy Accomplishments behind her. She wasn't a celebrity. And so really, it would be extremely intimidating to meet this storied family.

[B]

Beyond intimidating.

[A]

Okay, so apparently this event happened. The meet happened over a. Over Labor Day weekend at Hyannis Port. The annual Kennedy clam bake. Chandler.

[B]

What can you imagine?

[A]

You pull up. Oh, this is. No, I have the chills. Just imagine you're dating this American royalty, and you pull up and this. Dude, it's three white mansions on six acres of beachfront property. Like, yes, I would be embarrassed of myself, but I would also fully feel like this was the life I was meant for.

[B]

Oh, I. No, it's unfathomable. Unfathomable. I mean, to have grown up to knowing, like, of the family name and then to be. Feel like you have a chance at joining, that is out of control.

[A]

Out of control. I cannot even imagine how nervous she was and just how fabulous this weekend was.

[B]

Right.

[A]

So apparently Carolyn was completely shocked by how formal these Kennedy gatherings were, even though they were just family weekends. Everyone was in suits and dresses, but she did. She did dress appropriately. She wore a white silk shirt with a mauve blouse and a pink scarf draped around her neck. Very elegant.

[B]

Very elegant.

[A]

Carolyn, though, bombed her first dinner at the Kennedy compound. On that. Yeah, on that. I'm assuming this is in, like, Hamptons Hyannis Port on that Hyannis Port weekend.

[B]

No, no, it's in Massachusetts. Whatever. It's like, on the Tomato.

[A]

Tomato.

[B]

I think I'm. Yeah, I literally think I'm going to Hyannisport, like, at the end of August. Dramatic. Like a.

[A]

Like a Southern California hoe is all the same to me. Wait, you are going to Cape Cod?

[B]

Yeah, I'm going to Cape Cod in August.

[A]

Oh, for what?

[B]

For vacation.

[A]

I know, but, like, just. Just with Ben, like, the.

[B]

The group that I went to Nantucket with last year. Remember that whole thing? Remember when you were like, oh, I get it. You're going to Nantucket. Yeah, we had a blast. So we're.

[A]

Are there two extra spots?

[B]

No.

[A]

Can Kagan and I come?

[B]

No, there's not two extra spots. Sorry.

[A]

Wait, really, though? Are there really? For sure not.

[B]

I know for a fact there's not. And all the air mattresses are sold out on Amazon until the end of time. Whatever.

[A]

Okay, so she bombs the first dinner.

[B]

Wait, what happens?

[A]

So Ethel Kennedy, the matriarch of the family, comes to sit next to Carolyn, who had an empty seat next to her, and when she goes to sit down, everyone else stands. And can you imagine how formless family is they stand in respect to the matriarch.

[B]

No.

[A]

Can you imagine if Deb expected us to just, like, stand whenever she entered the room?

[B]

Never. Never.

[A]

Never. Absolutely not. So Carolyn, though, noticed that everyone was standing up a little late. It was kind of like this moment. And she was mortified that she didn't stand up quick enough, that she stood up late. Apparently, Ethel Kennedy. So this is another thing that I'm just very grateful about. Kagan's family. They, they're not interested in quizzing you on current events to see how learned you are. But apparently the Kennedy family was. So Ethel Kennedy loved to discuss current events and politics, and she quizzed Carolyn about Carolyn's thoughts on the federal assault weapons ban. Carolyn, I guess, was too busy listening to the Pop Apologist podcast to care about this ban or to think how many, you know, formulated thoughts about it. So Ethel told her, you might want to read up on that. It's quite important. And this was super embarrassing in front of everyone. Apparently. Ethel also says to Carolyn, a scarf in this weather. I'm feeling overheated just looking at you. And then Carol. Yes.

[B]

It's like, it's be. It's beyond bitchy.

[A]

That's the thing too, is like, you know, the person who's trying to embarrass you and make you look like a fool.

[B]

Yes, exactly.

[A]

Like if, if I get the vibe someone doesn't know what I'm talking about, I'm not going to lay into them.

[B]

Exactly.

[A]

Tell them they might want to read up on it, that it's super important. So anyway, quite, quite rude. And this really lays a foundation for their relationship. Carolyn doesn't enjoy being around his family, and that is a huge source of strain for them in their marriage. So apparently, Al, the dinner was not just the end of Carolyn's faux pas. The rest of the weekend was a disaster too. She missed a few meals because John forgot to tell her that there was a sign up sheet for breakfast and lunch. Seems a little strange that you'd have to sign up for breakfast and lunch.

[B]

It's a little campy for the America's Royal Family book. Yeah.

[A]

And she also had trouble keeping people's names straight. She put her foot in her mouth a lot and Ethel saw it all and was shaking her head during this weekend.

[B]

Oh, my gosh. Okay.

[A]

So. So moving on from this terrible weekend, though, to John's George magazine. So around this time, he's dating Carolyn. Things are getting more serious, Actually very serious. And he pivots from the handmade kayaks from the mass produced handmade kayaks business and creates George magazine. He receives 20 million to start the magazine from a mix of investors.

[B]

Okay.

[A]

And the magazine's first office is on the 41st floor of a Manhattan high rise. It's not glamorous, though. There's coffee stains on the carpet and the walls are super grimy. But he didn't care. He was so excited to launch this venture. And to launch.

[B]

This has Arthur George vibes to me. Maybe it's just the name. I don't know.

[A]

I don't know. I kind of love it. I kind of love it. I mean, as two people who have created like a little publication, as you.

[B]

Will, an audio publication, I'm allowed to, you know, shit and other people's side hustles and not my own.

[A]

Oh, right, right, right. For sure. You know how that works. We are famous for being hypocritical, if anything. Okay, so In July of 1995, after.

[B]

A year of dating.

[A]

Wow. This is impressive. John. And John proposed to Carolyn.

[B]

It is impressive because it's so fast.

[A]

It's so fast. I mean, that is just so hot. I love. It's the same thing as Megan and Harry. I love a fast engagement. To me, it speaks to passion. It speaks to romance. It speaks. Speaks to depth.

[B]

I mean, it just speaks to men wanting to settle down, which we love to see.

[A]

Which we love to see. It speaks to families being created. Okay, so In July of 1995, yes. After a year of dating, John proposes to Carolyn in a fishing rowboat while on a weekend at the Kennedy compound. Apparently gets down on one knee. This is all very the Notebook to me. The Notebook slash.

[B]

A J.

[A]

Crew fever dream. But he gets down one knee and he says, fishing is better with a partner. Everything is better with a partner. Will you marry me?

[B]

Okay.

[A]

Karen.

[B]

I don't love this. I don't love this. I don't love this metaphor. I. I didn't love the cruise liner one.

[A]

It's a little.

[B]

I don't love the fishing. It's super lazy. It's like, no Brad Falcon, it's not stirring at all. He doesn't even touch on her beauty, for the record.

[A]

No, he doesn't. He does not touch on how hot. How hot she is. And that is really, really terrible.

[B]

Totally. It's a travesty.

[A]

Now that I think of it. Kagan did not mention anything about my physical appearance during his proposal. And I'm going to tell him it must go in the vows.

[B]

I mean. Yeah, I just like. I don't know if you should still marry him, but I like.

[A]

I would like 90 of the vows to be about, like, different body parts and facial features. That is into.

[B]

He better start writing now.

[A]

Yeah. Because it better be.

[B]

Oh, wait, he is. You find him in the middle of the night, like, feverishly writing his vows. That's right.

[A]

I do. That's right. Just completely stressed. Just dripping with sweat.

[B]

Right.

[A]

By candlelight, with a fire lit.

[B]

Right.

[A]

Pen and quill. Okay. Apparently, Carolyn responds and says, I don't know. I'm afraid people will judge me, especially your family. And she's afraid she'll never be able to live a life marrying a Kennedy. So three weeks go by, and finally, Carolyn agrees to marry him. This I think, is super interesting because it really shows that she understood, like, she understood what the problem would be in their marriage and ultimately what it was that she did not like being a Kennedy and did not like his family.

[B]

Right, right. And I'm sure saw the strife of Jackie and, you know, she just wasn't blind to any of it.

[A]

Right. The ring was a delicate platinum band of diamonds and sapphires. It's just alternating diamonds and sapphires. It was similar to one that his mother had. They kept the engagement quiet for a few weeks and only told their closest friends because they knew the press would be all over them. Also, this was right before the launch of George magazine, and apparently someone leaks it to the press. So wanting the press to focus on his engagement, John made a public statement that they were not engaged. And this was very upsetting to Carolyn. Okay, so that is up to the engagement. Chandler, do you want to take us from here beyond the engagement and into. Into that stormy, stormy Martha's Vineyard evening?

[B]

So let's talk about a few fights that happened during their engagement. All right.

[A]

Okay.

[B]

John and Carolyn are out to dinner with friends, and what we're gonna see is that Carolyn is resistant to going to a lot of Kennedy family events, obviously, because it's terrible to be with his family. And so they sort of get into it, and, you know, he says, don't come with me. Hell if I care. I'm sick of having this same fight. And he says, you know, you're crying because you don't want to have fun on the beach with my family. Which is, like, not what it is at all. Like, they just sign up and for breakfast, lunch, or breakfast and lunch, and also wear suits and dresses. Carolyn gets up, she runs out. He turns to his friends. I mean, it's also, like, pretty tacky to fight in front of Your friends, in my opinion. But he turns to his dinner companions and kind of asks if he should go after her. And they're like, don't be an idiot. Go after her. And, you know, he was. Goes and looks for her in the streets of Manhattan, doesn't find her. And, you know, he says to them, she took a cab back to the apartment. I guess, what a big baby. Not a good look. And I think his friends try to reason with him and they say. He says to them, she wants to marry me and this is my family. Why can't she just get over herself? It's not that simple. And his friends say, do you know how hard it is to blend in with the Kennedys? You know, and now you're making her feel bad about it. Like, this would take a very long time to grapple with anyways. They make up. Well, yeah, go.

[A]

Well, I just want to say that I think this is a very good contrast to Prince Harry. Prince Harry knew that becoming a royal was absolutely going to be terrible. He understood what, you know, having to deal with his family was going to bring into Meghan's life. So I'm actually reading a. Basically a tome about the royals that just came out by Tina.

[B]

Oh, right.

[A]

Yeah, yeah, it's so good. I'm going to do a full deep dive on the pod. And anyway, I just want to say, though, that one of the things she says is that he tried to actually keep the her from the family from. For a while during that relationship because he knew how terrible it would be. So it's interesting that John did not have the same, I guess, perspective.

[B]

Okay. Okay.

[A]

Obviously, John's mother wasn't killed by the paparazzi, though, but his father was. I don't know. Anyway, just kind of an interesting contrast.

[B]

Right, Right. No, I think that's a great parallel to draw. So, you know, another fight happens, and this fight is pretty iconic. I'm sure everyone has seen the images of them fighting in Washington Square Park. And I mean, it's a very, like, heated fight. Right? Maybe just heated fights are in the brain because of Johnny and Amber. But, like, you know, he grabs her arm and it seems to, like, take off her engagement ring. She jumps back, jumps on his back to, like, get it back. And then he. He gives it back to her eventually. And, you know, she tries to take their dog's leash out of his hands. And he says, you've got my ring. You're not gonna get my do. Just like. And I'm taking the dog kind of moment from Legally Blonde.

[A]

But anyhow, the fights, the photos of them fighting really are so just, it's. They look extremely aggressive. Like, there's one point, like you said, he's sitting on the curb with his head in his hands, and she looks like she's screaming at him. There's another part where he looks like he's screaming at her.

[B]

Right.

[A]

So anyway, yeah, I think spicy, a little Johnny Amber vibes happening.

[B]

So two things here. One is that this fight is not about meeting his family. This fight is about his relationship with the press. And it was about actually a wedding that they had gone to a few weeks before, and they had been sat next to a New York Times society page editor. And, you know, Carolyn realized that was the only reason why they were invited was to, you know, have their names, you know, as part of the guest list, you know, at X, Y or Z wedding. And she just felt like people were using John. And she had said to him, you need to, you know, I guess, cut the nice guy act and, and not, you know, give in to the press and have some boundaries. Clearly she has boundaries herself. And she didn't.

[A]

She didn't like going to all those events.

[B]

Absolutely. And especially events where they're just being used.

[A]

For me, I mean, a fancy wedding, getting to dress up, doing all that fun stuff, like if my. The goal of my life would be to be so notorious and beloved that I'm just invited to all these events that I otherwise have like, no place at.

[B]

Right.

[A]

I mean, for me, it's just like such. It's not even a first world problem. It's like a first person problem. It's just like, oh, another fancy event. I don't want to go. And they're only inviting us because we're just so fabulous and famous.

[B]

But I think, like, the other aspect of this incident is that the paparazzi captures everything. And it's like they have a very serious fight about the way their different perspectives on press and, you know, like, their society life and it's all captured and that.

[A]

Obviously, much more comfortable with it, obviously.

[B]

And, you know, I mean, he's been photographed since he was a baby, but it's just the writing on the wall for why their marriage was so difficult and, you know, why it ultimately, like, was headed for a demise.

[A]

Right, Right.

[B]

So this is an interesting story that a couple weeks later, Carolyn flies to D.C. because she's summoned there by Ethel Kennedy, the very Ethel.

[A]

Who?

[B]

The one she snubbed by not standing up quick enough. Right.

[A]

And the one that did not approve her at first.

[B]

Okay, what's in and what's interesting? And this is why, like, I would have been so livid. She begs John to come with her. Like, she says, like, I don't want to go meet your grandma by myself. Like, and he. He's afraid of her as well. So he actually says he's got business to take care of at George Arthur, George Magaz or whatever, the sock magazine. And he. He stays. He literally cowers and doesn't go with her. And so she goes by herself, I guess. Actually, no. She brought a wing woman. But it's not. It's not. It's nobody.

[A]

It's not the same.

[B]

It cares about. It's not the same. It's like. I mean, I would literally have killed. I would have killed Ben if. Like, anyways, right. Sorry for another day. But so, you know, when Ethel comes out to meet her, she actually has this, like, very Queen Elizabeth, like, I don't know, scary, menacing moment where she says, you were afraid to meet me alone. You know, people think I'm scary, and they think that because it's true. And, like, who talks like that? Is this, like, freaking Judi Dench on Clickhole? Like, who's. Who is. It's just. It's just the amount of arrogance and self importance that the Kennedys have is insane.

[A]

Incredibly cinematic. What an incredibly, like, cinematic family and experience to be a part of and to have.

[B]

Right? And then what's interesting is that they start to sort of open up to each other. And she talks about, you know, what it's like to be married to a Kennedy and the difficulties, you know, and it's interesting because Ethel says, like, Ethel.

[A]

Does or Carolyn does.

[B]

Ethel talks. They both start to. Ethel, Excuse me. Ethel starts to talk to Carolyn about what it's like to be married to a Kennedy. Okay.

[A]

And the difficulties there.

[B]

She tells Carolyn that she repeats her mantra, which is I am enough, which is something out of like a 2020 therapist book, you know, talk space thing. But it's interesting that she. She says that. You know, she literally says that to herself, I am enough. Because there's such an imposter syndrome, you know, wow. With this family. And that. She says it will sink in eventually and that no one can take that away, not even the Kennedys. And she tells her. I know it is. And she tells her that she shouldn't let, you know, John or the reporters or anyone change who you are in her in here. Excuse me? She says that she shouldn't let John or reporters or anyone else change who she is, like, in here, which is. She points to her heart or something like that, which is like, wow, what a turnout. Very touching. It's, like, cinematic to go from, like, you're afraid to meet me alone, you know, because people think I'm scary. They think it's true. It's like Bourne. Jason Bourne or whatever.

[A]

Yeah.

[B]

So clearly this is some sort of turning point, and maybe this makes sense, you know, Carolyn, feel better about the trajectory of their engagement and their relationship moving forward. Okay, so let's talk about their wedding, which was iconic. It. It took a CIA level of effort to plan this wedding because it was a complete secret. Wow. And one thing I realized is. Or one thing that I saw was that John's gift to her was a wedding that felt real to them. It was a wedding that didn't have paparazzi or fans or the whole, you know, show dog and pony show. It was a very real wedding. And I thought that was so touching because knowing her perspective on the press and their life in the limelight, you know, he really. It was a grand gesture for him to have this wedding be a complete secret.

[A]

Yeah.

[B]

So just a few notes about the secrecy and how insane it was. The guests were given day's notice. Okay. And when they were given notice, they didn't know when or where it was going to take place because obviously the press would have had a heyday. So there was, like, no chance of leaks. I mean, only 40 people were invited.

[A]

And so 40 is so small.

[B]

Like, it's. So when you're from the Kennedys to the point.

[A]

Yeah. His family was not invited.

[B]

No. He only invited, like, one cousin from every family, which is pretty insane.

[A]

Yeah.

[B]

So 40 people, and they had no heads up. You know, they were just like. Basically, from what I've gathered, they were told to buy a plane ticket to Florida. Okay. When. When they were, you know, let in, like, hey, something's happening. They had to buy a plane ticket to Florida. And then from their flight in Florida, they were driven to a town in Georgia. They still don't know where they're going.

[A]

Okay.

[B]

And they got on a lobster boat that them then took them to the island, and they just, like, set off in darkness, like, nobody knew where they were going, even on the boat. And a lobster boat is not fancy. It is not a. You know, it's. It's not a river cruise. It is a, like, lobster fishing boat.

[A]

Right.

[B]

And they arrive to. It's just. I mean, there's footage because one of John's friends, Billy, captured everything with his like handheld camera, that's kind of the only footage we have. And they arrive to a twinkling light dinner and only upon rising the next morning do they realize where they are. Which is Cumberland island off of the coast of Georgia.

[A]

That's so cool. Like what an experience.

[B]

I, Yeah, I bought the, the secret tapes or something and it's like this whatever footage this is from Billy and it's, it's beautiful to watch. You can have my login. You're welcome.

[A]

We should, we should try to put some of it up on Instagram.

[B]

Yeah, yeah.

[A]

For the peeps.

[B]

So just a little note about this island. It's extremely remote and small. It's a mile off the coast of Georgia and only 50 residents live there, which is crazy.

[A]

Okay.

[B]

Yeah.

[A]

I mean it's just I, I love everything about this because I love the idea of a low key wedding as someone who's having kind of more of a, an actual three day affair. Right. I just love the idea of this casual island wedding. It's so raw.

[B]

Both, both have their perks. But you know, this was really such a beautiful juxtaposition for like the life that they'd had and the life that they were, you know, going to have that was unfortunately cut short. So let's talk about the ceremony. They had the wedding at a small church. I mean you'll recognize this church from that iconic photo which I'll post in the teasers of them leaving. You know, it's very old, there's no electricity, there's no air conditioning. And the guests are seated and ready to arrive. John arrives a little bit late because he claims he couldn't find his shirt. And Carolyn actually had a dress malfunction where when she was getting, literally getting the dress put on her, it wouldn't go over her head. So they had to like someone was like, had some quick thinking and they put a self silk scarf around her like head and shoulders and that was able to let the dress like slide down. But they had to redo her hair and makeup.

[A]

Oh my gosh. How stressful.

[B]

And like, I mean the dress is pretty simple looking but just knowing that there was this whole malfunction and that.

[A]

So there was no zipper on the dress?

[B]

I don't think so. Yeah.

[A]

Wow.

[B]

And, and so she was two hours late to her own wedding which caused there to be no daylight. And it basically turned into this, this stunning candlelit wedding because they just grab some of the religious candles from the, you know, the altar or whatever and lit those around the church.

[A]

Okay. That I have the chills. I'm just gonna say. I think that this is so cool. And it makes sense because that in that iconic photo of her exiting the church, where we all, you know, have a spiritual moment, witnessing that stunning, simple dress, I think that it makes sense now because they're in darkness. It's great that it's at night. So how. How interesting.

[B]

And I don't think that night weddings are really done all that much. Like, it was truly that they. That they were. That they left the church when it was, you know, dark outside.

[A]

Right, right. Wow.

[B]

So, yeah, I mean, and then they just have, like, you know, this intimate reception with. With people and with other dearest friends and family and. Yeah, it's just like, you know, an iconic moment that people really don't know about.

[A]

Is the video of the reception or is it of the church?

[B]

I think it's both. I think it's almost. It's not of, like, everything I'm gonna start saying finish. No, no, you should. You should watch it. It's lovely. And, I mean, you can hear some of their vows. I'm pretty sure you can hear his goodness. His speech to Carolyn, you know, at the dinner, where he says, like, really, no one has changed my life more than Carolyn or something like that. It's much better than the fishing speech, I'll tell you that much.

[A]

Wow.

[B]

Okay. Yeah. So, I mean, another note. Guests drove in convertible Jeeps, like, through the pouring rain to the reception. Like, it was very rugged. It was not super posh. Yeah.

[A]

Very cool. So, you know, this is something I want to say.

[B]

Yeah.

[A]

I want to say that on some level, it's like, if you had. I'm sure it would be beautiful, but there's something about, like, having a wedding in a rundown, you know, old church with no AC and then having to drive through the rain and, like, the ruggedness, the com. The reason why it's so cool and compelling is because it's set against all of their wealth and all of the event that could have happened. So I think that's kind of funny.

[B]

It's like. It's like a marvel that they were so rugged and undone for their wedding because they're so rich in, like, hoity toity.

[A]

Right?

[B]

Correct.

[A]

Amazing. Okay.

[B]

Exactly.

[A]

Can we talk about the dress, though?

[B]

Yeah, let's talk about the dress. So her dress was designed by Narciso Rodriguez. He was a friend of hers, you know, from her days as a Calvin Klein publicist. And. And this really, like, spotlighted him and catapulted him into, you know, stardom as a designer because it was so beautiful. And the dresses at the time were more ball gowny. They were much more, like big and ornate. And so, you know, this was kind of an iconic design because people were just not simplifying in this way. In fact, like, I even heard of one designer, I think it's one of the guys from Queer Eye, and he was like, you know, they. People wouldn't even feel comfortable wearing a slip dress out to an occasion or like a dinner party, let alone to their wedding. So it was just a very, very bold expression.

[A]

Well, I think that also, obviously it's emblematic of her personal style. It's very true to her, but also it fits the event. Right. A 40 person, very rugged, simple event. It definitely fits the event. And I think that I really wanted a simple silhouette for my dress kind of to go with a similar vibe, but I just almost felt like it didn't fit the event. Like I needed a dress that kind of was like, fit the mood. So anyway, I maybe I'm just apologizing for not having a simple, minimalist vibe, but I definitely want a Carolyn Bessette moment at my wedding weekend. Some simple silk.

[B]

Totally. Rehearsal dinner or. Yeah, okay. So, yeah, that's. That's the wedding. And I think it's definitely worth everyone watching any and all, like, films about this because it's just, it's really iconic and the photos are beautiful and they both just look stunning. And I think, like, the leaving the church photo is just now something I absolutely want at my future wedding. Like, it's just. It's so amazing. It's so, so much more special than any other staged, like, family photo or like here we're posing, you know, next to whatever.

[A]

Right.

[B]

Anyway.

[A]

Right, Absolutely. I mean, it's all about it. It's just. It's similar to the photo of them where she's wearing his jacket and leaning back into him and she's wearing a black dress and has red lipstick on. That iconic photo. Yeah. Anyway, just absolutely in love with them.

[B]

All of the photos that they have together, they just truly seem so passionate and.

[A]

Mm.

[B]

Right. So to take a sharp left, let's talk about their early marriage. And, you know, they have a blissful couple of weeks honeymooning. But, you know, upon returning to New York, the usual, you know, fanfare and press shenanigans just pick right back up where they left off. And we start to see that, you know, John is spending a lot of time working on George magazine. And if he's not Working. He's spending a lot of time with either his friends or, you know, the Kennedy family, which we know she doesn't love to join. So that's. They got married in 1996, and by 1998. Yeah, 1998, we start to see Carolyn in decline. Okay, we have a story from one of her friends who says she went to dinner one night when John was sick at home with the flu, and she made at least a half dozen trips to the bathroom and came back to the table with white rings around her nostrils. We went from bar to bar, and she wanted to come over to my apartment, but I said no, because I knew it would be an all nighter. I finally dropped her off at 3am the next morning. Obviously, she's doing heavy cocaine. You know, John asked the friend the next day, you know, why did you keep my wife out so late? And they say, a better question, John, is why did your wife not want to go home?

[A]

Well, because what I've read is that he got so busy working and as you said, like, going to these Kennedy events that she didn't really want to go to, and she was very lonely. Totally. And they were really not connecting because they didn't. They didn't enjoy their spare time in the same way.

[B]

Right, right. Which is. Which is very important.

[A]

Oh, absolutely, absolutely.

[B]

So I think a watershed moment or a turning point in, you know, their kind of struggle as newlyweds is when she runs into Michael Bergen, who, if you'll remember, was the guy he started that handmade kayak company with. Right.

[A]

Oh, okay. Yeah, the guy who started the handmade kayak company, the mass scale handmade kayak company, mass produced handmade kayak company with, I mean, John.

[B]

Yeah. Before magazine, interesting to note the iconic Mark Wahlberg, Calvin Klein ads. You remember those?

[A]

Yes.

[B]

He is the crotch in those ads.

[A]

Oh, okay. So he's packing some heat is what you're trying to say.

[B]

Yeah. Wow.

[A]

Deb's gonna be thrilled.

[B]

Hope nobody's.

[A]

Thank you for that note. Thank you for that detail.

[B]

You know, she runs into him and, you know, it's reported that he makes her feel like her old self again. And they meet for coffee, even at one point, you know, they're hanging out later into the night and they share a kiss, which is like, if you're in a happy relationship, you're really not gonna put yourself in those situations.

[A]

Absolutely.

[B]

I'll just like the.

[A]

The. You're so correct. It's like the kiss really wasn't where, like the turn happened. It was deciding to hang out with him after hours, likely, you know, because you're not going to be in an environment where that's appropriate otherwise.

[B]

Right.

[A]

And.

[B]

And as this kiss happens, she pulls away and stops and says what am I doing? She tells him it can never happen again. And she comes clean to JFK Jr. Okay, comes clean to John. And what's crazy is that, you know, she has a sale later.

[A]

She comes clean to JFK's, clean to.

[B]

His father, not to him. But if you, you know, if you come clean to like your passed away father in law, it's fine. But John poses as the police like and buzzes at Michael's door and Michael lets him up and John immediately just decks him in the face when he sees him.

[A]

Wow, that's hot.

[B]

After finding out. Yeah, it's pretty hot. So I guess, you know, this is.

[A]

When this interview about how violence is never the kind of answer.

[B]

But this doesn't end. This does not end like their emotional affair, which is what she tells JFK Jr that it really is. She says it's not sex, you know, it's. He just, you know, I can talk to him about my life and he understands me, yada, yada yada. And you know, they try, but they.

[A]

Continue to see each other.

[B]

They continue to see each other and this really makes JFK Jr. A upset. Obviously if you share a kiss with anybody and you're trying to restore your marriage, you should never see that person ever again, especially solo.

[A]

I just think that it's actually inappropriate once you're in a partnership, once you're in a marriage to have friends that you hang out with of the opposite sex. I just a. One on one, it's not appropriate. It's just really, I mean, do you agree or disagree?

[B]

I disagree. I don't think that it's like, I don't know, I think that they're like, they're like female friends, new best friends, like before he knew me that like.

[A]

Yeah, yeah, but I'm saying like new friends. I don't know, I guess I just mean. But I also think that like it's not appropriate to hang out with. Especially repetitively with one member of the opposite.

[B]

Oh yes, absolutely. Like repetitively after hours when you could be spending time with your partner. It's super weird. It's totally a red flag. I mean and of course if you've ever had any type of romantic connection to them, let alone like kiss them or your ex boyfriend. Yeah, yes. So you know, they try to give their marriage a second chance. They go to counseling. The counselor brings up her drug habits. This just sends her into a rage. It's not working. And, you know, they're sleeping in different bedrooms. At a certain point, JFK eventually just moves to a hotel. And it's just like this marriage, you know, has. Is crumbling so fast. I mean, it's only been two years.

[A]

Yeah.

[B]

And, you know, it's 1999. And, you know, just a couple of days. He. Just a couple of days before the inevitable plane crash, he is talking to a friend, and he says, I want to have kids, but whenever I raise the subject with Carolyn, she turns away and refuses to have sex with me. Wow. You know, he's sitting on the edge.

[A]

She's 33. Right. Because I remember that's when they.

[B]

Yeah, yeah, yeah.

[A]

Wow.

[B]

Okay. And, you know, maybe she just felt like she wasn't happy, and it's just so, so sad. So at this time, John has just recovered from an ankle accident. He was, like, a big sports guy, like, lots of, you know, fun sports when you're super rich and, you know, can own paragliding stuff. So he's recovering from his ankle accident, and he hasn't been flying this whole time because he's not allowed to fly solo. Well, he can't use his, like, one foot, obviously. So after, you know, getting out of his cast, he wants to fly. He is planning on flying himself to Hyannis Port for his cousin's wedding that weekend.

[A]

Okay.

[B]

Carolyn does not want to go. They are struggling big time as a couple, and she obviously has never liked being at Kennedy events, is not looking forward to this family wedding. And ultimately, you know, most devastating now, in hindsight, is she didn't feel comfortable flying with John. I never. Yeah, she never. She didn't feel comfortable. And she even said, I'm secretly terrified of flying with John because he's so easily distracted. He's got that adhd. She said, he doesn't seem to take it seriously enough.

[A]

Yeah, and this is where we get.

[B]

To some of the fatal mistakes and just scenarios. This is where we get to some of the fatal mistakes and, you know, factors that led to the, you know, tragic crash. Let me. So let me back up a little bit. So Caroline doesn't want to go. She's at this point, not going to the wedding. But in. During that week, Carolyn's sister Lauren arranges a meeting with JFK Jr. Herself and Carolyn, and she offers to come along to the wedding as moral support to Carolyn. And Carolyn agrees to then go, which then brings us to Friday afternoon, which is the day they're supposed to take off to go to the wedding.

[A]

That fateful day. Okay.

[B]

Yeah, that fateful day. And I didn't. Yeah, I. I did research on this crash, and there's a lot more to what happened than even what I knew before this. So there's. He's set to depart from New Jersey's Essex County Airport. And if anyone has ever lived in New York or been in New York and had to catch a flight on Friday, there is crazy traffic getting out of the city on Fridays. I missed my flight coming home when I was initially like, you know, moving here because of just Friday traffic. It's crazy. So the traffic is very bad. And John is now running late. Lauren, Carolyn's sister, is also running late from a meeting in the city. And, you know, this delay means that he now has to fly at night.

[A]

I heard she was also getting a pedicure too. So they were all late.

[B]

They were all late. And, you know, another factor is that John has only had this plane for, I think, 11 weeks. He's still getting used to it. And all of the flights before had been with an instructor. And even one of his flying buddies or somebody who was like, you know, in. In this realm with him said, hey, this is different from your Cessna. This is like a different plane that you really need to, like, understand and, you know, be up to speed with in order to fly it safely. But he doesn't take it seriously, as Carolyn has said. And he, you know, he. He insists on flying by himself. And also he doesn't take the, like, weather briefing. So basically, when you're about to fly, you should get the most up to date weather briefing, obviously. And he declines to do that. He doesn't, you know, he doesn't have time, doesn't want to. And the conditions are hazy and there's cloud cover above Martha's Vineyard, which is like the current weather conditions as he takes off, and under visual flight rules, it's barely acceptable for him to take off. So anyways, he takes off nonetheless.

[A]

And I think that, like, this is where. This is where it becomes interesting where it's clearly, honestly his fault. Like, he was just one of those dudes who thought that he was invincible and on some level just was not careful enough. Was not careful enough. And this is what went wrong.

[B]

Right, Right, absolutely. And. And what's really fascinating and terrifying about what happened with the crash is that it actually was a much more mental error than it was, you know, just crazy, crazy conditions. So he takes off. And one thing that you know, pilots have to do when it's dark outside and especially when they're near cities, is they can. They can tell the horizon line from, like, city lights. Like those can even break through cloud cover. But at a certain point, like, he cannot really tell, like, what's up or down. And he actually starts to undergo vertigo, right?

[A]

So he's in like this thick cloud coverage, and he just, like, he doesn't have his orientation of like, the. It's. The cloud coverage is so dense around him, he doesn't know what direction the plane is really going in in terms of if it's going up or down or if it's level. And I think he loses that orientation. And that is what. So he, like, he.

[B]

And what caused this? Yeah, and what caught just really quickly, what caused this is that he. He started to turn. And I guess what can happen is as you start to turn, it, it. It induces this vertigo where your senses start to feel like you're going one way and you're. The dials on the airplane show another thing.

[A]

Well, also, apparently there were like, there were instruments that were not. Like he wasn't flying with, that he should have been flying with. I read about. And. But haven't you had, like a strange. Like. I swear I've been in my car, you know, stopped at a stoplight, and I felt like it was moving strangely or like, just like I've had moments where I felt myself not have a total grip or bearings on what was going on. Like being in a plane and feeling like, are we moving or are we not moving? Like, you definitely, like, when you're on the ground, you. I can understand how you would lose your grip.

[B]

And honestly, this is one part of pilot training where you have to just. I was watching this video, and the guy just says you have to trust your instruments more than you trust your own senses.

[A]

Oh, interesting.

[B]

And so I'll read this one. You know, insidious thing about vertigo from this pilot talking about the crash, and he says that, you know, this vertigo happens when a pilot searches outside for a visible horizon, can't find it, then moves his head. The sloshing fluid inside the middle ear balance mechanism creates a false illusion. Vertigo says to the pilot, hey, you're in a turn. The pilot feels this sensation in the seat of his pants. He corrects with the yoke to level the plane, but in fact, the plane was always flying level and now it is in a banked turn. And the vertigo reassures the pilot. Okay, you stopped that turn. Well done. But the Turn has not stopped. The plane is still turning. Your middle ear balance system is out of whack and spitting out false messages. The plane tips farther and enters a graveyard spiral, which is the pilot is upside down, spinning, disoriented and confusing. There's no accident. It's awful. And, and this means then that all of the passengers would have been feeling this spiral as well. And so it's just a horrific end.

[A]

Yeah. I mean, can you imagine her final thoughts? She didn't even want to go to this wedding. She never wanted to get on up. She didn't even like flying with him.

[B]

Right.

[A]

This is why I think we have to trust our instincts. And I, I cannot even imagine the final, you know, their final terrifying moments as they plunged into the sea beside Martha's Vineyard.

[B]

Right. I mean I, I don't want to get on my soapbox here, but you know, there was a time in my life where I had a friend whose dad like flew planes and mom would not let me. Like we were going to fly to Vegas for her birthday and mom bought me a commercial airline ticket because she would not let me get in a small plane. And you know, nothing happened. Everything was fine, thank God. But like small planes are F U C K I N G Terrifying.

[A]

Yeah. And I also think that, and I was actually thinking about this as I was doing research for this episode and I just decided that my role is I will fly in small planes but with professional pilots where that's their full time career. I will not fly with hobbyist pilots. Like that is my mind.

[B]

I don't. Yeah. Hobbyist pilots especially. It's just, it's terrifying. And also, you know, I know we have like, I have friends whose parents fly and whatever and it's, it's totally that person's prerogative. It just scares me. And I mean I, I'm in the Travis Barker plane crash that was with a professional pilot. It's just I'm probably never gonna be rich enough anyways to like fly with like always private or ever part private. So. Right. It's an easy thing for me to rule out, frankly.

[A]

Just be like, I'm not. Yeah. 100 same.

[B]

Yeah. So I actually will never. I'm not gonna become that rich just because I'm just too afraid of flying private. Sorry.

[A]

Anyway. Just.

[B]

Anyway.

[A]

So incredibly sad, but very. Because like all these details about where they were at in their marriage, all of this stuff I really didn't know. And so I thought it was very intriguing. Intriguing to read about, you know, what their lives are really like what their marriage was really like. And honestly, I don't think they would have stayed together. I think they were on a collision course with divorce, really.

[B]

I think ultimately marriages where you, you know, are becoming a part of such a crazy established family that has so much writing on you expectation wise, like, I just think those marriages are kind of doomed.

[A]

I definitely think, though, I would have thrived as a Kennedy. Like, I think if they could have gotten past my murky history and just really just all of your.

[B]

The content, whether you're airing or dirty laundry. Yep.

[A]

My pure embarrassment.

[B]

Right.

[A]

If they could have gotten past the fact that I have a Patreon account, I really would have thrived as a Kennedy. I would have loved going to the events. I would have looked up the current events before meeting Ethel. I definitely would have killed it.

[B]

Weapons ban.

[A]

Yeah, exactly.

[B]

That's great. That's great. I'm sure you would have. Yeah. Anyway, Lauren, I think you would have been a stunning Kennedy. And honestly, I wish you would have become one just so that I could have some of the perks besides the flying.

[A]

I mean, my engagement photos were fully cosplaying as the Kennedys.

[B]

Like, aren't we all? Aren't we all?

[A]

Yes, we are. We all certainly are. Anyway, so I really thank you, Chandler. You did an amazing job recapping from their engagement on. I truly felt like this was so fun. Such a interesting and kind of different pop apologist episode from our usual just bantering. So, you guys, if you like the episode, please leave us a five star review. Let us know that you want more of this kind of narrative content, these deep dives. And I would love to do at least one of these. I would say once a month. Month.

[B]

Yeah, totally.

[A]

Or.

[B]

And send us suggestions for who you'd want.

[A]

Yeah. Of what you want us to dive into. Yeah, I kind of want to do like iconic couple Barack and Michelle. But then I also feel like it's too political. I don't want to get.

[B]

It's just honestly kind of boring.

[A]

Yeah. I feel like we all know it. You know what I mean?

[B]

I've told you how far I got into becoming. I love Michelle Obama. I just couldn't really get through her book.

[A]

Yeah. And I don't want to be accused of being like, you know, getting too political. So anyway, and I love. I want to do it on upside people, people we don't know that much about.

[B]

I think celebrities from history, too, are fascinating. I'll understand who Orson Welles is by then, hopefully. And who our actual presidents were.

[A]

Yeah, I want to try. I want to do maybe one on like, all of Gwyneth Paltrow's boyfriends. I feel like all of her relationships or yeah, like, even take that. That approach to it. So anyway.

[B]

Would be like, yeah, totally ripe to do. She's got so many. Yeah, absolutely. Yeah, plenty. Okay, giveaway time.

[A]

Yes. We have to do the giveaway. So, Chandler, we had 112 entries.

[B]

That's crazy.

[A]

So, yeah, it was really, really great. Thank you all so much for entering. We're not going to do a giveaway this month just because, you know, we want to give it a break. We don't want to get these things to get annoying. But we want to say thank you so much truly, for participating. It really helps. I mean, it's. It. The giveaways are actually what's really driving growth.

[B]

Yeah. They're fundamental part of our growth. So it. It helps so much. So thank you to everyone who entered. Everyone who entered twice.

[A]

And if out of the goodness of your own heart, you do want to recommend an episode to your followers and to link it, truly, it will. It will mean so much to us. And if you do that, I'll. I'll write you down and I'll put you on next month's. But.

[B]

Oh, wow.

[A]

Just, you know.

[B]

Okay, cool.

[A]

Yeah. Okay. So anyway, let's draw. So, Chandler, can you generate a random number, please, between one and 112?

[B]

Okay. 112. Right. Okay. Ready? Yes. Three. Yes. Two. One. It is number 74.

[A]

74. Oh, my gosh. Elena M. Young.

[B]

Oh, my gosh.

[A]

Elena M. Young. Elena Young. Elena. Hell, I love very.

[B]

Right.

[A]

She has been with us since the very beginning.

[B]

Literally since we had like under a hundred followers on Instagram.

[A]

I have every other giveaway winner we have not known. So this is like, this Truly, like, means, though. This is so fun.

[B]

It's really, really fun. I love it. I'm so happy because she deserves it. She's. She's been, like, spreading the good word. Yeah. Like we said, since day one, before we even had, like, actually good giveaways. I feel like when we had giveaways that were like, Here's $50 to Applebee's.

[A]

Totally. No, she's really a benevolent soul and.

[B]

Just such a supporter.

[A]

So anyway, this is so fun. So super excited that Elena won. Elena will reach out. Obviously. We'll hit you up where you can redeem your 500 shopping spree or walking pad. So exciting. And guys, next month we will be back with a giveaway. And we just appreciate everyone who entered so, so much. So thank you all, truly.

[B]

Thank you. Love you guys. Thank you, everyone.

[A]

Love you.

[B]

Bye.