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

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.

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.

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.

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.”

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.

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.

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]

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]

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.

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.

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]

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?

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.

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.

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]

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