Did Henry VIII Have An Affair With Anne Boleyn's Sister?

Summary

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Betwixt The Sheets: The History of Sex, Scandal & Society

Episode Title: Did Henry VIII Have An Affair With Anne Boleyn’s Sister?
Host: Dr. Kate Lister
Guest: Estelle Paranque (historian and author)
Release Date: November 21, 2025

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Episode Overview

In this lively and thought-provoking episode, sex historian Dr. Kate Lister is joined by historian and author Estelle Paranque to delve into one of the most pervasive Tudor rumors: Did Henry VIII really have an affair with Mary Boleyn, sister to his infamous queen, Anne Boleyn? Together, they unravel the tangled threads of myth, propaganda, and real historical evidence. Along the way, they place the Boleyn women’s experiences—and the origins of their reputations—under a critical lens, questioning the reliability of centuries of salacious storytelling.

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Key Discussion Points and Insights

1. Setting the Scene: The Boleyn Family Drama

• [01:47] Kate introduces the episode stating:
  “If there is one Tudor family who had more than their fair share of drama, it was the Boleyns.”
• The show sets out to separate fact from friction, asking what real evidence exists for the alleged affair.

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2. Who Was Mary Boleyn? Debunking Misconceptions

• [06:09] Estelle Paranque emphasizes the importance of understanding Mary as an individual before judging her reputation, beginning with birth order:
  “I do not believe that Mary Boleyn was the eldest daughter.”
• [07:49] Estelle reconstructs the sisters’ early court lives, noting:
  “I assume that Mary Boleyn goes back with Mary Tudor back to England, and Anne stayed in France …only one Mademoiselle Boleyn, and it’s Anne.”
• The widely repeated "English Mare" rumor about Mary’s promiscuity in the French court is discounted as baseless gossip, sourced from biased, anti-Boleyn, and non-contemporary Italians.

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3. Myth-Busting: Mary Boleyn as the ‘Whore of France’

• [09:24] Estelle asserts:
  “There’s no evidence of it. Absolutely zero.”
• [10:20] Kate summarizes this point:
  “So, like, we have already contemporary evidence from the time that Mary Boleyn was going like the clappers over in France.”
  • Estelle replies, “Nothing. And in France, zero… if there had been an English girl playing around … the gossip would have been like mental.”

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4. At the Tudor Court: Marriage, Money, and Muddled Motives

• [12:09] Mary’s marriage to William Carey in 1520 was unremarkable:
  • No rumors then connected her to Henry VIII.
  • Though Henry was present and gave the couple money, this fits his general patronage patterns—“He does give lots of money to other people.” [13:35]
• The timing and context do not suggest favoritism or romantic involvement.

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5. Mistresses and Patterns of Behavior

• [14:14] At the time, Henry’s mistress was Bessie Blount—unmarried, who bore him a son.
• Estelle points out Henry’s lack of interest in married women as mistresses, contrasting his behavior with that of King Francis I of France: “He’s a serial killer. He’s not a womanizer.” [15:52]
• While upending Henry’s image as a notorious womanizer, Estelle clarifies that his extramarital interests were fewer than commonly thought.

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6. The (Lone) Evidence: The 1527 Dispensation

• [17:24] The strongest evidence for an affair is Henry’s request for papal dispensation to marry Anne, claiming he had “known her sister in the flesh.”
• Kate (18:15): “See, that’s quite a smoking gun.”
• Estelle’s Alternative Theory:
  Rather than being a confession, Estelle suspects Henry was seeking legal insurance to escape marriage if Anne, like Catherine, failed to produce a son, reusing tactics he had previously employed:
  • “He’s already thinking about protecting himself… a backup plan in case anything was going quite badly with Anne.” [19:14]

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7. Questioning Motives and Gaps in the Story

• There are no contemporary rumors or specific timings of an affair in the 1520s.
• Later salacious allegations (Elizabeth I’s reign, 1574 Nicholas Sander) are seen as Catholic propaganda meant to discredit the Boleyn line as “whores”—not reliable history.
• Estelle: “Let’s look at the evidence: she was a married woman; we have no evidence of him going after married women… I do not see any problem here; I do not see any evidence.” [21:51]

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8. Mary’s Second Marriage & Life After the Court

• [30:20] Mary’s unapproved marriage in 1534 to William Stafford is attributed to love, not opportunism or palace plots.
• After Anne and George Boleyn’s executions, Mary lived a quieter life, banished from court, probably in relative obscurity until her death in 1543.
• Her descendants were favored by Elizabeth I; her line continues notably to figures like Princess Diana.

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9. Narrative & Legacy: Why Does the Rumor Persist?

• [39:43] Kate asks the key meta-question: “Does it change anything about our understanding of Henry VIII and the Tudors if this affair didn’t happen?”
• Estelle argues the persistence of the affair story serves to pit the sisters against each other, enhance the Boleyn “drama,” and satisfy the public appetite for historical scandal—“I just think people love making Anne Boleyn not liking any women in her life.” [39:59]
• Both conclude the legend likely says more about misogynistic and anti-Boleyn storytelling than the real historical record.

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Notable Quotes

• Estelle Paranque (on Henry VIII’s pattern):
  “He’s a serial killer. He’s not a womanizer—in the same way.” [15:52]

• Estelle (on the affair evidence):
  “The only evidence we have, this dispensation in 1527, is something that happened… I think he’s asking for a dispensation to protect himself again, to say, actually, we’ve been cursed. And also because the Pope is going to change.” [34:07]

• Kate Lister (on the legend’s resilience):
  “If there is one Tudor family who had more than their fair share of drama, it was the Boleyns. I mean, could you even imagine knowing these people?” [01:47]

• Estelle (on historical methodology):
  “If tomorrow we find a true evidence... fine. Then I would, you know, I have no problem saying that she was a mistress. All I’m saying is that let’s look at the evidence.” [21:51]

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Timestamps for Key Segments

• 01:47: Introduction to the “Boleyn drama” and popular perceptions
• 06:09–10:42: Debunking Mary’s “French court” reputation and alleged promiscuity
• 12:09: Mary’s marriage to William Carey; discussion of wedding and court patronage
• 14:14–17:44: Examining Henry’s mistresses and character, challenging the “womanizer” trope
• 17:24–19:14: The 1527 papal dispensation—what does it really mean?
• 21:51–26:02: Alternative interpretations and lack of hard evidence for any affair
• 30:20–37:33: Mary’s later life, second marriage, and family legacy
• 39:43–41:34: Do the facts alter our view of Henry VIII and the Boleyns? Why does the story endure?

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Tone and Atmosphere

Witty, candid, and irreverent. Kate and Estelle blend intellectual rigor with cheeky humor and empathy for the historical women at the center of the scandal. The conversation is peppered with playful skepticism (“He’s a serial killer, but he’s not a womanizer”) and a shared frustration at lazy historical tropes and misogynistic narratives.

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Conclusion

Through close scrutiny of available evidence, Estelle Paranque casts doubt on the long-held tale of an affair between Henry VIII and Mary Boleyn. The rumor, she suggests, is better understood as a product of later political agendas and popular imagination than as solid fact. Both speakers advocate for a reexamination of these women as historical actors in their own right—not merely as scandalous footnotes in Henry’s reign.

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Final Thought from Estelle: “Could we just stop pitting against one another Mary Boleyn and Anne Boleyn? … I’m questioning it, I’m questioning it.” [41:28]

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For More
Find Estelle Paranque on Instagram and YouTube for discussions on Tudor women—“Be nice, even if you disagree with me.” [41:04]

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Transcript

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[Kate Lister]

Hello my lovely betwixters. It's me, Kate Lister. This is betwixt the sheets. I am Kate Lister and you are you. I'm so glad that you're here. Thank you. Thank you for stopping by. Once again, I'll put kettle on. But before I do, I am going to have to warn you. This is an adult podcast spoken by adults, other adults about adulty things in an adult who wake up ragin subjects. And you should be an adult too. Oh God. Do you feel safer? I feel safer. Right, let's get that brew going. Everyone knows that Henry VII was knocking boots with an Sister Mary before their affair got going, don't they? They do. They made a whole film about it, the Other Berlin Girl and that was based on Philippa Gregory's novel of the same name. It is known. Or is it? What if they weren't what if that didn't happen? What is the evidence that we actually have for that? What if it's all Catholic propaganda and Mary never did such a thing? Oh, what then? Well, today we. We are going back to the Tudor court and we are going to attempt to tease out fact from fiction, or rather fact from friction in this case. But what was Mary Boleyn really about? Did she have an affair with Henry? Did she? Well, let's find out. Hello, and welcome back to Betwixt the Sheets, the history of sex scandal in society with me, Kate Lister. If there is one Tudor family who had more than their fair share of drama, it was the Boleyns. It was. I mean, could you even imagine knowing these people? What was their Christmas family newsletter like? Of course, we know all about Anne's rise and then her eventual fall from grace. But what about Mary? What about her sister Mary? She was also knocking about the court, and given that she was A, a female and B, had a vagina, she would have caught the eye of our mate Henry viii and possibly another body part as well. But what evidence is there to the claim that they actually did have an affair? Who was Mary Boleyn? What was her life like? How likely was it that she would have had an affair with the king? Well, joining me today is the always fabulous historian and author Estelle Perrong, who isn't entirely sold on this Mary Henry affair idea. And she is going to help us pull apart some of the theories and apply historical rigor to these claims. So without further ado, let's get on with it. Foreign hello and welcome back to Betwixt the Sheets. It's only Estelle Parank. How are you doing?

[Estelle Perrong]

Hello, Kate. I'm so happy to be here with you again.

[Kate Lister]

So much fun. Last time doing. You are actually here by special request. I requested you to come back because I saw the podcast interview you did with the dashing Dan Snow. Saw because it's now available on YouTube where you just very casually dropped a bomb that I thought, right, well, we're going to have her back on to talk about that because you were talking about Anne Boleyn. Just, just in a few seconds, you just went, yeah, I don't think her sister Mary did have an affair with Henry viii. Boom. Absolute scenes.

[Estelle Perrong]

I know. Like, it's crazy because everyone talk about it and everyone, everyone think that there is something and yeah, I think we need to dive into what we know. I think we need to dive into the sources. Okay.

[Kate Lister]

Kate makes films about this, Estelle.

[Estelle Perrong]

I know, I know. The Other balloon girl. Right? Oh, my God. I. I hate that movie. Oh, my God. Also, like, I just feel like, you know, it was just a way to create this kind of Mary Bolin being the good girl, the good Boland girl, and Anne Boleyn being like, the awful. Yeah. You see what I mean? But first of all, first of all, before we dive into what I think, and you're gonna think it's crazy, and. And I love crazy, but please bear with me, okay?

[Kate Lister]

Because everybody, I have a reserve judgment. Okay?

[Estelle Perrong]

No, I love it. No judgment. Yeah. But you will be judging.

[Kate Lister]

Okay?

[Estelle Perrong]

And the thing is that I'm not saying it never happened. Okay? I'm not. And first, I'm gonna go back to a few things. I'm gonna go back to who was Mary Boleyn, because I think everyone need to really understand. And also, the first thing that we got wrong about her and why it leads me to my conclusion where it's like, wait a minute. Are we sure that she was Henry VIII's mystery? So let's go back to who she was.

[Kate Lister]

All right, let's do it. Okay.

[Estelle Perrong]

Thomas and Elizabeth Boleyn had three children. It's what we know. Anne Boleyn, Mary Boleyn, George Boleyn. I chose that order because I do not believe that Mary Boleyn was the eldest daughter.

[Kate Lister]

I'm glad you said that because I've often thought it's weird if she was.

[Estelle Perrong]

Exactly. And also, like, so, I mean, some historians make, like, compelling argument of why. And again, I'm not saying that unless we have the birth certificate, obviously everyone is allowed to speculate. But. But for me, sending your second born daughter to Austria and France, wanting her to receive an incredible education, wanting her to learn French to be taught in a certain way, and then your firstborn daughter, well, you're like, I don't really care. That makes no sense to me. And people are like, oh, that's because Thomas Boleyn preferred Dan Boulain. We have no evidence of that. We have evidence that they did get on really well. That doesn't mean she's the favorite. And I think it's just wrong to assume it that way.

[Kate Lister]

So this is Thomas Boleyn because it was Anne who got sent over to France to absorb court life and learn all this stuff and get an education. The whole time, Mary is just back in England kicking up her heels going, why not me, daddy? That's the crux of this.

[Estelle Perrong]

Exactly. Like, I'm your first daughter, you know? And so what's very interesting is that because anne was in Mecala 1 when Mary Tudor, so Henry VIII's sister, was sent to France to marry Louis XII of France, which she didn't want to do. And Anne could not go back in time to England to then to go to France. It was agreed that Mary would take her place in the household of Mary Tudor until Anne arrives in France. And so at some point, you have the two sisters together in France. But we know that Mary Tudor, you know, her short reign as queen of France doesn't last. Louis XII is gonna die. Francis the first is gonna become king of France, and his wife Claude of France, gonna become queen of France. And then what I know for sure, Kate. Okay, there's lots of things that I don't know for sure. But what I know for sure is that Anne Boleyn stayed and Mary Boleyn didn't.

[Kate Lister]

Right. In France.

[Estelle Perrong]

Exactly. What I also knew, like, people said that Mary stayed. So we about like 1515, and people said that she goes back to England in 1519. I have no records of that. I have no records of two Boleyn girls from 1515 to 1519. There's only one Mademoiselle Boleyn, and it's Anne. So I assume that Mary Boleyn goes back with Mary Tudor back to England, and Anne stayed in France. Now, I don't know if you've heard that big kind of myth around Mary Boleyn, that she was the whore of Francis I, that she went through the.

[Kate Lister]

French court like a bad kebab. Yeah, I've heard that. What was she called? The great whore? The English mare.

[Estelle Perrong]

Yeah, the English mayor. Exactly. There's no evidence of it. Absolutely zero.

[Kate Lister]

Well, there is. There is a letter that somebody wrote.

[Estelle Perrong]

Oh, yeah. But that letter is, like, from someone who just, you know, he hates the bullets.

[Kate Lister]

It was years after the fact. Right.

[Estelle Perrong]

It's years and years after the fact. Is Venetian, is Italian, and he's just, like, hating on the Berlin faction, hating on the break with Rome. And so it's so easy for him to make that type of comment. But that's not. Primary source. That's not reliable. Not absolutely not reliable. And there is nothing in the French sources that says that Mary Boleyn was the mistress or had anything with France. And I don't even believe she stayed long enough to have anything with Francis the First. You know, she goes back to England, so that's one thing. Right?

[Kate Lister]

So, like, we have already contemporary evidence from the time that Mary Boleyn was going like the clappers over in France.

[Estelle Perrong]

Nothing. And in France, zero.

[Kate Lister]

Right.

[Estelle Perrong]

And trust me, if there had been an English girl playing around, like, I mean, let's you. We know the French, right. The gossip would have been like mental.

[Kate Lister]

Yes. Like, come on, someone would have said something. I'm with you there. Okay. Yeah, you've convinced me of that one.

[Estelle Perrong]

I even think that we would have had comments about it later on by Catherine de Medici and Elizabeth I. You know, like we would have something that is much more convincing than this.

[Kate Lister]

Quite shocking because I don't know how old she was, but I think she was very old. She's like 15, 16ish. At the time. Would that have been quite shocking for a well to do born English woman to suddenly kick up her heels with.

[Estelle Perrong]

With the king of France, you don't think. There is very little evidence when it comes to Francis I approaching his wife's also his queen's household and ladies in waiting. He has enough women. Right. He's a total womanizer. He's totally like partying and doing all the things that he shouldn't be doing. He's not a great husband, I'll give you that. You have to understand that Claude, his wife, the queen of France, is staying. Usually, usually she's sometimes with her husband, but usually she's away. Right. I do not see how he would have had enough time anywhere to spend some time with the Boleyn girls and do anything with them. And one of them, as I said, is for sure returning back to England because in the records there's only one Boleyn girl.

[Kate Lister]

Okay, well argued, Estelle. Well argued. Right?

[Estelle Perrong]

Yeah. I think on that one, I think that one is kind of easy. Bear with me because it will help me make my case for the next one.

[Kate Lister]

We are ready and waiting. Here we go.

[Estelle Perrong]

So I give you a bit more context as well. Mary Boleyn comes back and in 1520, she's. She has an arranged marriage with William Carey. Okay, now that's where it becomes very interesting for me at the time. We have no rumors when she's getting married. There are no rumors at the time.

[Kate Lister]

Okay. When she's marrying, was it William Carey? There's no connection with Henry viii?

[Estelle Perrong]

No.

[Kate Lister]

He was at their wedding though, wasn't he?

[Estelle Perrong]

Yes. And he's giving them money.

[Kate Lister]

That's all the proof I need, quite frankly.

[Estelle Perrong]

But they'll do things. But Kate, like, I think it's interesting because people start like making assumptions here. Again, I'm not saying it's. I'm not saying it's impossible. Right. I'm Just saying, you need to bear with me in terms. Let's just go through the facts and then let's try to understand them. Okay. And there's a lot, obviously, of my interpretation of these facts. All right. But bear with me. What we have here is a king that. Let's not forget that Thomas Boleyn is very important now at court. And he has one of his daughters in France, or she used to be in France, and she's going to come back. The other one got a good match. She's married to William Carey. Cary is someone that Henry VIII himself really respect and really liked. So he worked for the king before. And now we have, as term of evidence of Henry V giving lots of money to the couple. He does give lots of money to other people.

[Kate Lister]

Okay, okay. So it's not an outlier.

[Estelle Perrong]

I mean, if you're just looking at that, for me, there's nothing truly shocking that he's favoring Thomas Boleyn and his family and William Carey that he really liked and that had worked for him before and giving him money, being there at their wedding. I do not see here any kind of problem. What I know is that at that time, when 1520, 1521, 22, 23, 24, 25, there is no big rumor, and I'm going to tell you why as well. There's no big rumor of him having Mary Bolin as his mistress. He has another mistress.

[Kate Lister]

Oh, it's Bessie, isn't it?

[Estelle Perrong]

Bessie Blunt. Yeah.

[Kate Lister]

Okay.

[Estelle Perrong]

And that woman is not married.

[Kate Lister]

Interesting.

[Estelle Perrong]

And that is important as well, you. That people are just assuming. Do you really think it's easy to just. You have the choice of mistresses and you're going to choose a married woman?

[Kate Lister]

I mean, he wouldn't be the first, but I'll grant you, it throws up some problems.

[Estelle Perrong]

It wouldn't be the first, but, like, he has already one that is not married and is going to give him a son.

[Kate Lister]

Good point. Okay. When did Mary even arrive at the Tudor Cup? Before she got married.

[Estelle Perrong]

So that's the thing is, like, people say she comes back from France in 1519, and then, you know, in 1520, she marries William Carey. So then she's kind of like part of the court life, because William Carey is very much part of the Henry vii. She's got life.

[Kate Lister]

She's got like a year or so before she gets married. Ish. Yeah. Okay.

[Estelle Perrong]

She had way more than that because she was in England way longer. She did not stay in France until 1519. She went back in 1515.

[Kate Lister]

Okay, okay.

[Estelle Perrong]

So she gets married. Bessie Bland is going to give a son to Henry in 1519, and then she's going to marry herself, you know, someone in 1522. And that's where it gets very interesting in many ways, because people are saying that's at that moment that Henry VIII would have gone closer to Mary Boleyn. But again, I'm making the point of, why would he have chased a married woman? Not unheard of, but it's not something that he did before.

[Kate Lister]

Does he do it. Does he do it with anybody else? Is there any evidence with his behavior about him chasing married women?

[Estelle Perrong]

No.

[Kate Lister]

Interesting.

[Estelle Perrong]

No. Also, I mean, I hate Henry Diaz, but I'm gonna say it anyway.

[Kate Lister]

Okay.

[Estelle Perrong]

Gosh, it's so hard for me, guys. I told you I was going to make you laugh today. He's a serial killer. He's not a womanizer. In the same.

[Kate Lister]

It's a low bar, everybody. But he's. Oh, dear. He's a serial killer, but he's not a womanizer.

[Estelle Perrong]

It came across so badly. But please bear with me here. What I'm saying is that, you know, when I talk about Francis the First, and he's, like, basically screwing anything that he gets. Henry VIII is not the same Henry, isn't he? He's not happy, but more than you'd think.

[Kate Lister]

More than this, like, womanizing, wenching, eating, like, raw, like, you know, cooked meat and all this kind of reputation he's got, when you actually get into it, he didn't have that many.

[Estelle Perrong]

I mean, there's six wives, and he's gonna kill two of them, and he's gonna kill five more women. So, I mean, he's a horrible, horrible. He's a psycho. He's a monster. He's a. He's a serial killer. He's a. He's a misogynistic bastard, you know? Okay, the. The podcast is not about him, but. But you see, you get my point. But he's not a womanizer.

[Kate Lister]

Okay.

[Estelle Perrong]

And so I do not see why he would have been so interested in Mary Boleyn. Right. There's no thing about Mary in any records. Sorry to say that. I'm sure I'm upsetting her now, if she's a ghost or something. But there's nothing very special about her, like you say. I don't see why he would have, like, you know, created so much problems for me. It makes absolutely no sense. Okay.

[Kate Lister]

Okay.

[Estelle Perrong]

Now, what's very interesting is the fact that in 1527. So the evidence we have of the affair, it's in 1527. So remember from 1520 or all these years that I mentioned before, there's nothing about it, but in 1527, there's love letters.

[Kate Lister]

There's no rumors. There's smoking gun.

[Estelle Perrong]

There's going to be a rumor. But that comes later on. That comes when it's tried to discredit Elizabeth I. So it's much later on saying that actually he was the father of her cousin. Right. Henry Curie. So in 1527, he did something that gives the strongest claim to this affair. Okay. He's gonna ask for a dispensation from the Pope to be able to marry Anne, saying that he had known her sister in the flesh.

[Kate Lister]

Okay, see, that's quite a smoking girl.

[Estelle Perrong]

Yeah, but. Okay, let me make my case first.

[Kate Lister]

Yes, please continue.

[Estelle Perrong]

You need to come to flow with me with this.

[Kate Lister]

I'm flowing with you, baby.

[Estelle Perrong]

Let's go.

[Kate Lister]

Right.

[Estelle Perrong]

Tell me, when did he do the exact same thing exactly at the same time? About 15:27. He's also saying that the reason why he wants a divorce is because Catherine of Aragon had slept with his brother.

[Kate Lister]

Oh, yes.

[Estelle Perrong]

So he wanted an annulment of his marriage. In my head, it is not far fetched. And I know that some people are going to attack me about come, come at me. It doesn't matter. I'm just saying prove me wrong. Give me more evidence. Because so far the two evidence we have is him saying in 15 minutes 27, actually, I have had sex with your sister Mary. So I need dispensation. Well, I think it's not too far fetched to think that he's already thinking about protecting himself in case it doesn't go well with Anne Boleyn.

[Kate Lister]

I'll be back with Estelle after the short break.

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[Estelle Perrong]

Can I make my sight softer?

[Marc Maron]

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[Kate Lister]

Oh, so you're thinking that Mary was a backup.

[Estelle Perrong]

I'm thinking that he's thinking I sounded like a nedbar. No, come on.

[Kate Lister]

Come on. Madder theories have Been put forward with less evidence. Let's go for it.

[Estelle Perrong]

I'm thinking that he was thinking he's gonna get off this marriage with Catherine of Aragon thanks to this. The fact that she slept with. Well, she didn't. But the fact that she might have slept with his brother and a way for him to protect himself in case there's any problem with Anne, in case he needs to get rid of her as well later on because she has the same problem as Catherine. He needs a thing. And so he uses the kind of same argument. And the reason I say that is because obviously, like, well, the dispensation is not going to be granted because we know that the Pope can't grant it. But also it's what we talk about evidence. For me, there's this. That's the only strong evidence that would actually. Yes, you're right. Convince us that, yes, maybe Mary was his mistress. But what I don't understand is why did he wait for so long? Why is there exactly no record of when she was exactly his mistress? Why was he not more specific about what time she was mistress? Why is there no more rumors and discussion about it? And the rest that we have is much later on is on Elizabeth I's reign and it's by Nicholas Sanders in 1574 that is making that claim that basically any bull and women are whores. Right? Yeah, even discussion. Also, Kate, isn't it crazy? I'm sorry, but I'm gonna continue with this because I really believe in it. Like in a way, you know, it's not just Mary Boleyn. There are like, then there are rumors that actually Elizabeth Boleyn, the mother of Anne and Mary, was also his mistress.

[Kate Lister]

Oh, I have heard that one.

[Estelle Perrong]

Yeah. But that's all absolutely not true. No evidence, not nothing. And I think that he thought that maybe like this, he didn't want to put the dispensation on Elizabeth Boleyn, but more on Mary Boleyn. So that for Elizabeth Boland, there's absolutely no evidence. But you see, or not understanding Henry, Henry was calculating. It is his reformation. Not on a religious level, on a political level, on making money, on being powerful. It's on him. The way he treats his women, the way he treated his wife, the way he thought about women. I mean, when you really look at it, the way he refused to arrange marriages for his daughters, the way he was so controlling for me, it's not far fetched to think that he was trying to protect himself. Of like, imagine the Pope would say yes, then the Catholic Church would recognize, obviously, the marriage, but then he would have a backup plan if in case Anne does like, which he did like. Did like Catherine not giving him a melee and say, wait a minute, actually. And then he will have gone back and said, actually, I need an annulment. Because now I realized that though you've given me a dispensation for this because I slept with her sister. I think that's now why we've been cursed. And so I needed another annulment. I think that. I think that was the end game. And why I think it's so close or why do I think that it is possible is because we have nothing else now. If tomorrow we find a true evidence of like. Exactly. We have Henry giving money not to William Carey, but like also Mary directly. Or we have a letter that he says to Thomas Boleyn, you know, your daughter Mary is such a delight and I loved spending the night with her. Fine. Then I would, you know, I have no problem saying that she was a mistress. All I'm saying is that let look at the evidence, she was a married woman. We have no evidence of him going after married women. He give money to William Carey. Of course he was going to give. William Carey was a very good courtier to him, very loyal. He really liked him. He also really liked Thomas Boleyn. I do not see any problem here. I do not see any evidence. But the only evidence we have, this dispensation in 1527, is something that happened. He tries to do exact same thing to get an annulment for the dispensation he got before with Arthur and Catherine. And I think he's just trying to reproduce this situation for him to give him a backup plan in case anything was going quite badly with Anne, which in the end he wouldn't need. But that's another. Obviously another story. But do you see why I think there's so little.

[Kate Lister]

I see what you're saying is that he was already thinking about who brothers and sisters and husbands and wives all sleeping together because he had to argue why he shouldn't be allowed to marry. He didn't have to be married to Catherine anymore is because Catherine was married.

[Estelle Perrong]

To his brother and he brought a dispensation for that.

[Kate Lister]

He brought the dispensation. The thing is, like, if he goes on record going, yeah, I did have sex with Mary, so I should be allowed to marry her sister as well. It was like, is he lying to the Pope if he says that? If, like, would that be. He is.

[Estelle Perrong]

I do not think he would care.

[Kate Lister]

You don't think that he would. See, that's interesting. Okay.

[Estelle Perrong]

I don't think he would care at all.

[Kate Lister]

I mean, he has been telling porcupiers to the Pope kind of the whole way through because he was going, look, I need to divorce my wife because of spiritual matters. And then the Pope found a load of love letters that he'd written to Anne Boleyn and, like, talking about her tits and was like, I don't think this is a spiritual matter, Henry. Thank you very much.

[Estelle Perrong]

It's definitely not.

[Kate Lister]

I mean, so he's not above. He's not above lying to the Pope, is he?

[Estelle Perrong]

No, absolutely not. And also, I'm saying, are we allowed to just say that this rhetoric around the Bullen women. I just think that maybe we need to stop seeing these women, Mary and Anne, as these whores of England. Right. And that's my problem. I think it's just used and used and used against, then later on against Elizabeth the first, mostly. Right. It's like to tell her that all the women in her family were whores. Right? Were awful. Her lineage, or Bullen lineage is awful. And I'm just saying. Hang on, slow down. Who is saying. Who is saying that she was a mistress? And even if she was. Even if she was like, I'm just wondering why we know so little about.

[Kate Lister]

It, if you're right, that Henry was kind of viewing the sister as a backup plan. Could. And we are in speculation territory now, but we've passed that point a long time ago, so I'm gonna keep going. Could that explain this kind of weird move that Mary does slightly later where she gets married without the king's permission and without her sister's permission to a guy who is slightly below her station and kind of throws everyone this curveball that she just literally turns up and goes, oh, this is William Stafford over here. We've got married. Sorry, Forgot to tell anybody. That's always a weird move that she did.

[Estelle Perrong]

Okay, so that's an interesting one because, like, I would not have necessarily, like, link the two together. I think the story with William Stafford and Mary Boleyn, I would go with. This time, I would go with, like most historians and people think is that obviously it must have been a love match. Did you think that in a way they would not get upset with her because they owed her or something? Like, you know, in a way that, you know, by. By letting Henry saying that they had an affair. It was. She was giving him a safety net in case everything was going wrong. And then he could go back and say, oh, yes, you gave me a dispensation, but actually I should get an annulment because we see again, I've been cursed again for sleeping with the same flesh and blood. And my part, you know, like all of this that, you know, he tries to do with. With Catherine of Aragon and Arthur, I don't know, I think it's. For me, I think it's. Here it's more memorable and being in love with William Stafford and not wanting to let anyone tell her what to do.

[Kate Lister]

Oh, hang on a minute.

[Kerrygold Advertiser]

So.

[Kate Lister]

So when you said that, he said what he said so he could have a backup plan. You're not thinking that he wants to eventually marry Mary if the thing with Anne doesn't work out? You're thinking that in case he wants to divorce Anne, he's got something record to say I was not the sister. Yeah, that makes a bit more sense now. Okay.

[Estelle Perrong]

Because it sees you as well, Kate. You know, think about it. The Pope is going to change again. So then he can always blame on the other Pope. It's what he did. It's actually what he did with Arthur and Catherine. We have to understand, to get married to Catherine of Aragon, he got a dispensation saying that she was the wife of his brother. She promised that nothing happened. But then. But then he goes back and he said I should have an annulment because it's clear that actually she lied to me. Something happened because we've been cursed. And you know, it's in the Bible, if you sleep with your brother's wife, you will not have. I think it's children, but what he means here is sons. And I think here, at the same time, he's thinking, oh, my God, I need to protect myself. I don't have another brother for Anne, so what I'm going to do, he said, I slept with her sister. I'll get a dispensation for that. Why would he need a dispensation for that as well? Like, I have no clue. Why would it be a problem anyway?

[Kate Lister]

I don't know.

[Estelle Perrong]

There would be no problem. And then say, oh, the Pope who gave me the dispensation because he thought, let's. We need to go back in 1527 when he does it, when you're back there, he thinks that the annulment is going to be given to him. The sack of rome comes in May 1527. He doesn't understand quite clearly how much Charles V is going to have control of the pop. So he thinks that he. He's always had a good relationship, so he thinks it's an easy way for him to do it. Do you see? I mean, I do. He also wants a protection. He wants to be able to get another annulment in case Anne doesn't give him sons. That's what I think. That's what I think it's all about. Because what bugs me is that we have nothing else concrete. Okay, maybe. I don't know if we have contemporary rumors in the 1520s. I don't know. We don't. As I said, we don't have a starting date and an end date for. We just say in the 1520s, Mary Boleyn and Henry VIII were sleeping together. Okay, when? How so? You telling me that he was going to William Carey's house, screw his wife, give them money for that? So she's a whore and everyone's happy. No one mentions anything, and no one mentions everything. And there's no starting date and an end date. And also, I go back to my first. First point. Why does he need to do that with a married woman? He never did before. Bessie was not married when he was with her.

[Kate Lister]

Take me to Mary's second marriage then, because I interrupted you and you were.

[Estelle Perrong]

On a roll there, William Staff. I just think it's more of a love story where she was like, she didn't want to take the risk of them saying, he's not high enough for you, and so she just did what she wanted to do. Also, I think by that point, you know, Mary Boleyn was like, you know, of course she gets banished and she's not, you know, and it's quite hard for her. But at the end of the day, in many ways, it gives her protection to be away from all this madness anyway, because, you know, she does. This is like in 1534. She gets married to William Stafford in 1534, and Anne Boleyn had given birth to a girl still getting pregnant, but, you know, there's still the. Oops, that's.

[Kate Lister]

And Mary Boleyn's first husband. I forgot to even ask you about him. He's dead now, presumably if she's married someone else.

[Estelle Perrong]

Yeah, yeah, okay. Yeah, he's dead. Yeah. He died, I think, late 15. 1520s. I think he even dies before Henry made the claim that she. He had slept with. With Mary.

[Kate Lister]

Interesting. Okay, so you think that she really.

[Estelle Perrong]

Did love William Stafford, Mary Boleyn? Yeah, I think. I think she did. Yeah.

[Kate Lister]

Yeah.

[Estelle Perrong]

I mean, obviously I wasn't there and. But I just think that what are the other reason for her to. To marry under her status?

[Kate Lister]

It was a dumb call. And then she didn't even tell anyone about it. And then obviously, they got really mad. And one of the surviving letters we have of hers is her writing to. Is it Thomas Cromwell, you know, going, oh, please let me back. I won't do it again? And you're sort of reading through it and, like, I've gotta say, you know, I've never been in that situation, so maybe she was just panicking when she was writing it. But, like, she doesn't come across as particularly bright in that letter.

[Estelle Perrong]

Yeah, I mean. I mean, who does? Maybe it's just her emotions, you know, taking the best out of her.

[Kate Lister]

She's very, very emotional. She's flirting with danger when she's writing it because she says something along the lines of, like, oh, you know, we can't all be queen, or something like that. It's like a weird. Like, she. It's alarmingly close to, well, treason if she's not careful.

[Estelle Perrong]

Exactly. But also, you know, I think that we love the idea that Maribelin was actually the first mistress, like the first Boleyn mistress to Henry viii, and that Anne was the clever one for saying, because how you treated my sister, now I want to be queen. You know, that's the whole. That's the whole kind of story. Right. The storyline, me. I would say that Anne could have said the same about Bessie Blunt. I don't think she would have used her sister. I think she would have said, well, you have a mistress. She gave you a son. I don't want to be in that position.

[Kate Lister]

Yeah, do you?

[Estelle Perrong]

So in. I don't think that we need, like, to. To people, the two sisters against one another. I'm not saying it's not possible. I'm not saying that Mary. I'm 100% sure that Mary Boland was not Henry, this mistress. I'm saying I have a doubt. And my reasons for it is because of these three reasons. The first one is he's not a womanizer and usually didn't go after married women. The second is, like, the money evidence for me is not a real evidence. And there are no other evidence at the time in the 1520s about Mary and Henry. They're not even seen together. Being seen together.

[Kate Lister]

Did people know about Bessie?

[Estelle Perrong]

Yeah.

[Kate Lister]

Yeah, they did. Okay.

[Estelle Perrong]

And also, he elevated her. He gave her a lot. Well, of course she gave her son, but, you know, like, he was obviously. And that's what people say. Oh, but he was giving Lots of money to the couple, but he was giving lots of money to his courtiers as well. So is it the couple or was it William Carey? Who knows? And then. And my third one is the fact that I find it very interesting that in 1527, he uses his brother as a way to get rid of Catherine. And I know he's smart. He's a smart serial killer. He's thinking, okay, but what if Anne is not going to give me what I want? And then, you know, we're married, the Catholic Church, I will need something. And I think he's asking for a dispensation to protect himself again, to say, actually, we've been cursed. And also because the Pope is going to change. You can always say, oh, but you know, the. The former Pope, he didn't really know what he was doing. You're a better one. And you know what? I'm saying that now we've been cursed. We didn't have son. And I've just said I slept with her sister. With her sister. So I think it's a problem. My question is, though, I've never heard any problems about that. Like, it would have been a problem if Arthur and. And Henry's here. That's a problem, because they are brothers. But Anne Boleyn and Mary. I do not.

[Kate Lister]

That was the biblical verse, wasn't it, that he was citing? It's like, you shall not lay with your brother's wife. Not. You shall not lay with the woman you're trying to knob sister. That's. That's not.

[Estelle Perrong]

There's no. There's no. Yeah, exactly.

[Kerrygold Advertiser]

Right.

[Estelle Perrong]

So I don't know why it was a dispensation. I think it's weird that he comes up with it in 1527. Obviously, it happened before. I don't know. I just. I'm just saying, if it happened, if it's true, if Mary Boleyn is the mistress of Henry viii, fine. I'm not. You know, I'm happy for people to prove to me that.

[Kate Lister]

Give me more evidence.

[Estelle Perrong]

I need a bit more. I just need a bit more. Because then Nicholas Sander is 1574, and it's a direct attack on.

[Kate Lister]

Yeah, he doesn't care. Well, he doesn't get. He never. He never even met her, did he?

[Estelle Perrong]

The.

[Kate Lister]

The guy who called her the big.

[Estelle Perrong]

No. But he said, like, they've always been rumors, you know, even Eustace Sheppy, you know, he's so. He's so. How do you say it? You know, he attacks Anne Boleyn in most of his letters.

[Kate Lister]

Oh, he would have mentioned something, wouldn't he? Even I know Chapuis was an elite gossip.

[Estelle Perrong]

Yeah. And also, like, he. I don't have a huge record. Like, I mean, I haven't gone through all his letters, like, you know, all of them, but I. On top of my head, I can't remember anything about Mary.

[Kate Lister]

What happens to Mary Billing then? Just to round this off, because I often think, like, whatever she was up to, she was clearly at the center of this, like, kind of dragged into this court madness, intrigue, even if she wasn't having an affair with Henry viii. And then your sister gets accused of shagging your brother, and then they both get executed. I mean, what do you do? Where do you go?

[Estelle Perrong]

Well, the truth is, like, we have so little records on Mary Boleyn. Right. Like, we have so little on her. And all we know is that obviously she lost her sister and her brother, but also before that, she was banished from court. She's. You know, the family doesn't really want to talk to her anymore. We have no records, as far as I know, of her going back to Hever Castle. You know, her parents are gonna die. They don't last long. And Mary dies in 1543, I think. But there's no much record of her. She's not in Hever Castle where she grew up with Anne. She's probably spent more time at Hever Castle than Anne. There's little evidence regarding, like, what's happening to her. However, we know that obviously she gives birth to Catherine Carey, who is Mary Sir Francis Knollys. And she's gonna have lettuce Knollys. And that side of the family is, in a way, doing well. You call it doing well being a betrayal bitch. But Lettuce Knollys is a betrayer. But that side of family is very much favored by Elizabeth I. Catherine Carey is in the household of Elizabeth I. And then obviously, lettuce not list later on. So in a way, she keeps quiet. She removes herself from everything.

[Kate Lister]

Get your head down.

[Estelle Perrong]

Yeah, I think it's quite probably very tragic the. The end of her life where she lost everyone, you know, her sister, her brother, then her mother, then her father. So there's not much, but what we know is that her family obviously continues. Right. I mean, that. That's from that side of the fact. It's through Mary Boleyn that, you know, Diana, like, was Prince Diana was.

[Kate Lister]

Yeah, yeah.

[Estelle Perrong]

You know, a descendant and everything. So.

[Kate Lister]

I'll be back with Estelle after the short break. Hi.

[Kim from Pen Holderness]

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[Estelle Perrong]

Can I make my site softer?

[Marc Maron]

Can I make my site firmer?

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[Kate Lister]

Does it change anything about our understanding of Henry VIII and the Tudors if this affair didn't happen? I mean you know, apart from the facts like you know, you might have to like rejig a few things but like does it disrupt the narrative? I'm just curious as to why you think we're so ready to believe it.

[Estelle Perrong]

I don't think it changes much if it happened or if it didn't happen. I think it just changed the storyline of having the bull and horse so he gives the and also like putting so much rivalry between the two sisters which I don't again we don't have enough evidence for me to to agree to that. You see, I mean like people were saying oh yeah they didn't like each other or didn't get on. I think people just love making ambulance not liking anyone any women in her life. You know, like that's why she's also pitted against Jane Boleyn, you know her sister in law and and all of this and I think there's so little evidence now again and anyone listening to us, I am not saying that Marybolin was not for sure 100 sure. Not Henry VIII's mistress. I'm just saying, do we know enough to be sure that she was well argued?

[Kate Lister]

Estelle, you have been marvelous to talk to. I'm sure that we'll have a lot of people doing a lot of thinking after this one and if they want to know where they can find you. Where are you?

[Estelle Perrong]

Well, I'm on Instagram.

[Kate Lister]

Leave her alone. Don't physically seek her out.

[Estelle Perrong]

I'm on this.

[Kate Lister]

Be nice.

[Estelle Perrong]

Yeah, be nice. Be nice. Even if you disagree with me. But I'm on Instagram and YouTube. I'm happy for you to disagree with me. You know, I know a lot of people really believe in that affair. Lots of historians do. I'm just questioning if I've missed anything that is so big, please let me know. But, like, I do. I do. Could we just stop pitting against one another? Mary Boleyn and Anne Boleyn.

[Kate Lister]

You're just disrupting the narrative slightly. Just questioning it.

[Estelle Perrong]

Yeah, I'm questioning it. I'm questioning it.

[Kate Lister]

Right. She's just got some questions, that's all.

[Estelle Perrong]

I'm a lad.

[Kate Lister]

You have been marvelous to talk to. Thank you so much for coming on.

[Estelle Perrong]

Thank you so much for having me, Kate.

[Kate Lister]

Thank you for listening. And thank you so much to Estelle for joining us. And if you like what you heard, don't forget to, like, review and follow along wherever it is you get your podcasts. I know everybody always asks you to do that, but it does actually help. Coming up, we have got an episode on the truth about mythical women and another on the origins of Aphrodite all coming your way. If you would like us to explore some subject or if you just wanted to say hello, then you can email [e-mail] this podcast was edited by Tim Arstle and produced by Stuart Beckwith. The senior producer was Freddie Chick. Join me again. Betwixt the sheets. History of Sex scandal in society. A podcast. A history hit. This podcast contains music from Epidemic Sound.

[Jonathan Fields]

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[Estelle Perrong]

Can I make my site softer?

[Marc Maron]

Can I make my site firmer?

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