While with Catherine of Aragon, Henry had multiple mistresses, one of his mistresses ended up being his second wife. She is easily the most well-known wife, which is strange considering she’s the wife we know the least about.
Henry’s second wife was Anne Boleyn, the second child of Sir Thomas Boleyn and Elizabeth Howard. She was born in England circa 1501 and in, what we believe to be, 1513 she moved to France to serve as a lady-in-waiting for Mary Tudor, Henry VIII’s sister, during her marriage to King Louis XII. After Louis died, Anne stayed in France for seven years to be a lady-in-waiting for Queen Claude, the wife of the new king, Francis I.
While in France, Anne learned all the skills that were expected of a lady at court. These skills also allowed her to form a close connection with the French and English royal families.
When Anne returned to England in 1522, she and her older sister, Mary, became ladies in waiting for Catherine of Aragon, King Henry VIII’s first wife. Anne would be Catherine’s lady-in-waiting for seven years before she was removed from her position.
Henry VIII, who was 34 at the time, first became infatuated with Anne, 25, in the year 1526 and he needed to be with her. She resisted Henry’s (word for like pushing and yeah) for her to become one of his many mistresses because she only wanted marriage. Over the next year, Henry’s desire for Anne continued to grow as well as his need for a male heir. In 1527, Henry would ask to annul his marriage to Catherine of Aragon in order to be with Anne Boleyn.
Henry would be secretly married to Anne in January of 1533. Anne, at the time, was three months pregnant with their first child, Elizabeth I, one of the most famous queens in England history. Henry and Anne’s marriage was bigamous, the act of marrying someone while already legally married to another, since his marriage to Catherine of Aragon was not annulled until May of 1533. After the annulment between Henry and Catherine, Anne would be escorted by river to the Tower of London, where she prepared for her coronation. Anne was crowned Queen in Westminster Abbey on June 1, 1533, when she was six months pregnant. Elizabeth I would be born on September 7, 1533.
During Anne Boleyn’s time as Queen, she always supported the King’s decision; all of his new religious and political policies. She would also promote new educational identities for monasteries, since they were no longer under the protection of the Catholic Church. She was also the first royal patron of the great court artist Hans Holbein, a German-Swiss Northern Renaissance artist who painted not only Anne, but two more of Henry’s future wives.
Henry and Anne would try to have kids multiple times, as Henry still craved for a male heir, but they would experience a loss in the year 1534; resulting in Henry beginning to grow superstitious that since his and Anne’s marriage was bigamous, they were cursed to only have female children. This resulted in Henry growing further from Anne, slowly beginning to find a new wife.
In 1535, Anne would be pregnant again. During this pregnancy, Anne began to grow worried about the consequences of either: losing the baby or the baby being a female, since Catherine of Aragon, Henry’s first wife, would die in January of 1536, Henry would be able to marry a new woman, rather than his ex-wife. He chose to continue to be with Anne Boleyn until she gave birth. A few days after Catherine’s death, Anne would give birth to a stillborn male child.
Since Anne failed to give Henry a male heir, he started to find someone who will.
As Anne was dealing with the loss of her second child, Henry would begin to court a new woman, Jane Seymour. Henry would give Jane gifts like a locket with a painting of herself in it, which Anne ripped off her neck in a fit of rage. As Henry continued to send gifts to Jane, she started to reject him stating that if he must send her gifts, he should wait until they were married, using the same tactic that Anne used to be with Henry originally.
Henry decided that he wanted to pursue Jane as a hope to get a male heir. On May 2, 1536, Henry had Anne sent to the Tower of London with a charge of adultery with various men and even incest with her own brother, George Boleyn. Anne would beg for Henry and try to prove her innocence, but Henry, now besotted with one of Anne’s own ladies-in-waiting, ignored her protestations. Henry ultimately decided that Anne’s fate would be execution.
On May 6, 1536, Anne would write her final letter to Henry. The letter read:
Sir,
Your grace’s displeasure and my imprisonment are things so strange to me, that what to write, or what to excuse, I am altogether ignorant. Whereas you send to me (willing me to confess a truth and so obtain your favor), by such a one, whom you know to be mine ancient professed enemy, I no sooner received this message by him, than I rightly conceived your meaning; and if, as you say, confessing a truth indeed may procure my safety, I shall with all willingness and duty, perform your duty. But let not your grace ever imagine that your poor wife will be brought to acknowledge a fault, where not so much as a thought ever proceeded. And to speak a truth, never a prince had wife more loyal in all duty, and in all true affection, than you have ever found in Anne Boleyn – with which name and place I could willingly have contented myself, if God and your grace’s pleasure had been so pleased. Neither did I at any time so far forget myself in my exaltation or received queenship, but that I always looked for such alteration as I now find; for the ground of my preferment being on no surer foundation than your grace’s fancy, the least alteration was fit and sufficient (I knew) to draw that fancy to some other subject.
You have chosen me from low estate to be your queen and companion, far beyond my desert or desire; if, then, you found me worthy of such honor, good your grace, let not any light fancy or bad counsel of my enemies withdraw your princely favor from me; neither let that stain – that unworthy stain – of a disloyal heart towards your good grace ever cast so foul a blot on me, and on the infant princess your daughter.
Try me, good king, but let me have a lawful trial, and let not my sworn enemies sit as my accusers and as my judges; yea, let me receive an open trial, for my truth shall fear no open shame. Then you shall see either my innocency cleared, your suspicions and conscience satisfied, the ignominy and slander of the world stopped, or my guilt openly declared. So that, whatever God and you may determine of, your grace may be freed from an open censure; and my offense being so lawfully proved, your grace may be at liberty, both before God and man, not only to execute worthy punishment on me as an unfaithful wife but to follow your affection already settled on that party for whose sake I am now as I am, whose name I could some while since have pointed unto – your grace being not ignorant of my suspicions therein. But if you have already determined of me, and that not only my death, but an infamous slander must bring your the joying of your desired happiness, then I desire of God that he will pardon your great sin herein, and likewise my enemies, the instruments thereof; and that he will not call you to a strait account for your unprincely and cruel usage of me at his general judgment-seat, where both you and myself must shortly appear; and in whose just judgment, I doubt not (whatsoever the world may think of me), mine innocency shall be openly known and sufficiently cleared.
My last and only request shall be, that myself only bear the burden of your grace’s displeasure, and that it may not touch the innocent souls of those poor gentlemen, whom, as I understand, are likewise in strait imprisonment for my sake. If ever I have found favor in your sight – if ever the name of Anne Boleyn have been pleasing in your ears – then let me obtain this request; and so I will leave to trouble your grace any further, with mine earnest prayer to the Trinity to have your grace in his good keeping, and to direct you in all your actions. From my doleful prison in the Tower, this sixth of May;
Your most loyal and ever faithful wife,
Anne Boleyn.
On Friday, May 19, 1536 before a crowd of up to 3,000 spectators, Anne, who was 35, was led to the scaffolds on Tower Green. She calmly delivered a speech in which she accepted her fate and asked all present to pray for Henry. She took off her French hood and knelt before the beheading block, the sword taking her life a few moments later.
Sources:
Anderson, M. T., et al. Fatal Throne: The Wives of Henry VIII Tell All. EMBER, 2020.
Anne Boleyn | Biography, Children, Portraits, Death, & Facts | Britannica, www.britannica.com/biography/Anne-Boleyn. Accessed 11 Feb. 2026.
Anne Boleyn, departments.kings.edu/womens_history/anneboleyn.html. Accessed 11 Feb. 2026.
Anne Boleyn | Tower of London | Historic Royal Palaces, www.hrp.org.uk/tower-of-london/history-and-stories/anne-boleyn/. Accessed 11 Feb. 2026.
“Anne Boleyn Letter to King Henry VIII 6 May 1536.” English History, 17 Jan. 2022, englishhistory.net/tudor/letter/queen-anne-boleyn-letter-king-henry-viii/
“Anne Boleyn.” Wikipedia, Wikimedia Foundation, 25 Jan. 2026, en.wikipedia.org/wiki/Anne_Boleyn#:~:text=At%20the%20court%20of%20Margaret,for%20women%20of%20her%20class.
“Hans Holbein the Younger.” Wikipedia, Wikimedia Foundation, 1 Feb. 2026, en.wikipedia.org/wiki/Hans_Holbein_the_Younger.
“The History behind the Fiction: Anne Boleyn’s Brothers – Alison Weir.” Hachette UK, 6 Feb. 2020, hforhistory.co.uk/h-for-history-posts/2017/05/15/history-behind-fiction-anne-boleyns-brothers-alison-weir/.
The Six Wives of Henry VIII. Meet the Wives. Anne Boleyn | PBS, www.thirteen.org/wnet/sixwives/meet/ab_handbook_fate2.html. Accessed 11 Feb. 2026.
Theanneboleynfiles. “Anne Boleyn and the French Court 1514-1521.” The Anne Boleyn Files, 22 Feb. 2016, www.theanneboleynfiles.com/anne-boleyn-french-court-1514-1521/#google_vignette.