Back in May we covered Anne Boleyn’s trial and execution, so it seems only right we cover happier times in her life, or at least the rise that made her so famous. Today we’re going to address the question of when she first caught Henry VIII’s eye and what exactly those early months and years looked like. With the benefit of hindsight we so quickly jump from Anne arriving at Henry’s court to the political battles of the divorce, but there was a lull in-between that helped dictate where the ugly mess ended up. The “when” is important, too, because it speaks to what everyone’s motivation was – Anne’s, Henry’s and the councilors at the center of court.

For those that know their Tudor history, the terrain of Anne Boleyn can start to feel old. She means something to a great many people and she is one of those historical figures where even the smallest details can become centers of heated debate – her birth year, for example, can still send people into a tizzy.

But a few years ago I read something about this courtship that jumped out at me. It wasn’t necessarily new information, so much as framing a fact I had taken for granted as important to how we think about this woman and this relationship. Henry and Anne wrote to one another for years, particularly in the early days when they were often separated. Those letters, or what remains of them, have become the pillar on which we base our interpretation of their dynamic, timing and motivation. They are, however, one-sided – only some of Henry’s letters to Anne survive and none from her. As a result, our sense of their courtship is incomplete and wholly lacking Anne’s voice.

And the letters themselves, written at the height of Henry’s newfound ardor, have made the absence of Anne’s response feel like noise when in fact it isn’t. As Henry pours out his heart, her silence feels pointed, creating a vacuum on which we have painted a portrait that is barely human. She has become the archetype of the “other woman,” the second wife, the younger, glamorous model who sailed in from France with sophistication, education and European worldliness. The gap between his letters starts to sound like a studied seduction from a woman who knows exactly what she’s doing – in other words, playing hard to get.

But Anne did respond. She was also a young woman in her 20s with a background that prepared her to be a courtier and perhaps marry a nobleman, but in no ways grounded her for the role of royalty.  We have no idea what she thought of Henry’s attention in those early days. We have no idea if becoming queen was a motivation of hers until the wheels of the machine were in motion. We are left with analyzing her actions and movements and applying them to a series of portraits, some of which are copies from after her death, of a slim, dark-haired woman the painter has lent a Mona Lisa smile.

So first, some very basic background: Anne was the daughter of Thomas Boleyn and Elizabeth Howard. The Howards were closely tied to the Tudors, chiefly by the marriage of Thomas Howard, 3rd Duke of Norfolk and Anne of York, daughter of Edward IV and sister of Henry VIII’s mother, Elizabeth. The 3rd Duke’s father, the 2nd Duke, rose up the ranks quickly during the reigns of Henry VII and early years of Henry VIII and had a champion in Katherine of Aragon. He died in 1524, his title and power transferring to his son, Anne Boleyn’s uncle.

As a child, Anne was sent abroad, joining the households of Margaret of Austria, Duchess of Savoy (aunt of Charles V, Holy Roman Emperor) and Claude of France (daughter of Louis XII and wife of Francis I). She spent her adolescence the charming pet of her mistresses and was, by all accounts, well-liked and successful. She was also exceedingly well-educated for a girl thanks to an exposure to the humanist and reformist thinking that were sweeping Western Europe and soon to reach England. Unsurprisingly, she developed certain French mannerisms and courtly graces that helped set her apart from other women once she returned home early in 1522.

And as for the England she entered as a young adult, Henry VIII had been on the throne for about 13 years, the same amount of time he had been married to his brother’s widow, Katherine of Aragon. A series of miscarriages and stillbirths had been offset by the birth of one healthy child, Princess Marry, in 1516 who remained her father’s sole legitimate offspring. He also claimed one bastard son, Henry FitzRoy, via his mistress, Elizabeth Blount. By now the chances of Katherine delivering the longed-for heir were remote – she went through her last pregnancy in 1518 and never conceived again.  For a man as aware of his role and reputation as Henry was, the absence of sons was a humiliating blow, one which was soon to beg the question: Surely, there is something wrong with this marriage, not me?

Anne, however, didn’t swan into London looking to catch a king, however it was expected that she would do her time at court before marrying a nobleman of her father and uncle’s choosing. One early candidate was her cousin, James Butler, future Earl of Ormonde, which would have seen Anne sent off to Ireland. The match, which had the blessing of Cardinal Wolsey, fell apart for unknown reasons.

Soon after this, Anne developed a relationship with Henry Percy, heir to the earldom of Northumberland. Had that marriage gone ahead, it would have been quite the coup for the Boleyn family and, indeed, it was what the couple appears to have wanted. And it is here where we truly delve into a debate of timing, for there are only a few things that we know:

• Anne Boleyn was at Henry’s court by March 1522
• Certainly by 1526, Henry was in hot pursuit of Anne
• Henry Percy was married to Mary Talbot by (at the very latest) the summer of 1526
• And thus, somewhere in-between Anne’s arrival and Percy’s marriage, the two had a relationship that may or may not have caught Henry’s attention, but certainly prompted Cardinal Wolsey to put the kibosh on it

Historian David Starkey argues that Percy’s marriage to Mary Talbot definitely happened by August 1526, but likely happened a year earlier in August 1525. This is actually over a year later than where it’s usually dated.

Yet another bumper rail on how this relationship is considered is the question of Henry’s relationship with Mary Boleyn, Anne’s sister. The traditional narrative is that the two had a multi-year long sexual relationship during which Henry might have fathered Mary’s two children, Katherine and Henry Carey, who took the surname of Mary’s husband. More recently this has been challenged by those who argue there is little evidence to suggest that Mary’s relationship with Henry was anything more than fleeting and, certainly, it’s worth considering why Henry didn’t jump at the chance to acknowledge yet another son, even if a bastard, as another sign of his potency. He acknowledged Henry FitzRoy, why not Henry Carey?

Regardless, Mary was pregnant with her son by the middle of 1525, which is generally marked as the demise of her relationship with the King and the beginning of his infatuation with her sister.

In light of this relationship, most historians date the launch of Henry and Anne with 1525/1526 and that’s rather critical. If you allow that Henry didn’t become interested in Anne until one of those years, then his concerns about his marriage pre-date their relationship. Prior to 1525, Henry was consulting questions as to the validity of his marriage and it then poses the question: What would have happened to Katherine of Aragon had Anne Boleyn never entered the scene? Certainly there would still have been complications given her familial ties to the Holy Roman Emperor, but would the idea of an annulment have garnered more domestic support had Henry’s councilors thought the end result was another lofty foreign alliance and not the rise of an unknown woman with ties to the Howards?

Starkey posits that Anne had caught Henry’s eye earlier. That as early as the Christmas season of 1524/1525, Henry decided he wanted Anne as his mistress and asked Wolsey to break Percy and Anne up. Following his timeline, Anne and Percy had fallen in love and decided to marry sometime in 1524, Wolsey brought the matter to Percy’s father, the Earl of Northumberland, around June 1525 and the Earl stepped in and had his son married to Mary Talbot by August.

And yet another of Anne Boleyn’s biographer, Joanna Denny, puts forth an entirely different timeline. She states a more classical interpretation that Henry Percy and Mary Talbot were married much earlier, in the winter of 1524, pushing his relationship with Anne to 1523. Her evidence for this is a letter from the Earl of Northumberland dated in the summer of 1523 that complains about the expense of traveling to London to sort out his son. If true, it begs the question, what was Anne doing between 1523 and 1525? Denny believes she had been removed from court by her father and sent back to Hever Castle, their home, until the scandal died down from the fallout of the Percy connection.

What we do know for certain is that by the autumn of 1525, Anne was back at court as a lady-in-waiting to Queen Katherine and by the following year, an emotional affair would develop quickly.

To me, the two biggest questions are how long was Henry involved with Mary Boleyn and was Henry really the reason Anne and Percy were pushed apart? I don’t have a concrete opinion of either at this point, for it’s not completely out of the realm of possibility that Wolsey nixed the marriage for reasons that had nothing to do with Henry. I also admit that I haven’t paid too much attention to the new scholarship on Mary Boleyn – it’s on my list (and my bookshelf, for that matter), but I haven’t yet had a chance to delve in. That said, annual grants were made to Mary’s husband between 1522 and 1525 and then stopped, suggesting that they may very well be related to Henry’s relationship with his wife.

So, let’s reference Eric Ives, the godfather of Anne Boleyn scholarship. He believes that Anne’s and Percy’s relationship took place in 1523 and was interfered with by Wolsey that summer. He acknowledges the possibility that even so, Percy and Mary Talbot didn’t marry until August 1525, per Starkey’s argument. He also says that Wolsey’s stance on the relationship likely had nothing to do with Henry and certainly nothing to do with his feelings for Anne, for in 1523 he was still involved with her sister.

This does not, however, address the question of when, then, did Henry notice Anne. And in fact, given that he was sleeping with Mary Boleyn, it’s unlikely that Henry didn’t know who Anne – and the entire Boleyn family – was. Thus, this was not love at first sight, the way it is sometimes portrayed in television dramas of the relationship. So, taking into consideration all of the above, here’s a rough timeline accounting for multiple conflicting views:

• March 1522 – Anne makes her debut at Henry’s court
• 1522/1523 – A potential marriage with James Butler is in play and may have gone as far as a betrothal
• Late 1522/first half of 1523 – Anne and Percy are involved and marriage is under discussion despite Percy’s earlier pre-contract with Mary Talbot
• Summer 1523 – The Earl of Northumberland, at the behest of Wolsey, comes to London to sort out the matter
• June 1525 – Mary Boleyn becomes pregnant with her son
• August 1525 – Legal complications thanks to Percy and Anne having made some sort of commitment to one another delay Percy’s wedding to Mary Talbot until this point
• Second half of 1523 – second half of 1525 – Unknown time for Anne. She may have left court and been living at Hever; she may have remained at court the entire time. Or some mix of the two.

This doesn’t rule out Starkey’s theory that Henry became interested in Anne as early as Christmas 1524. Interest doesn’t necessarily preclude him with sleeping her sister and it’s entirely possible that his affair with Mary Boleyn ended earlier, her son having been fathered by her husband.

Certainly, if Starkey is correct, then if Anne was sent from court by her parents in the wake of the Percy drama, then she was back by late 1524, making her absence about a year long – more believable than a two-year-long hide out while her sister was still in the King’s favor. It also provides just the right amount of time for Anne to have begun a flirtation with the poet, Thomas Wyatt, yet another admirer of Anne’s.

No matter what the build up, we will never know exactly when Henry first approached Anne. We do, however, know that in the beginning he was looking for a mistress, not a wife – whatever his concerns were about Katherine of Aragon and their marriage, his mind had not yet jumped from anxiety over the succession to sourcing the next queen from his court. And because of this, I’m having a hard time making the jump to Henry propositioning a woman whose sister he was still actively sleeping with, a strong argument for the relationship being over by the time Mary conceived her son OR for the “approach” not happening until later in 1525. If the latter, then how likely is it that Henry, who liked shiny things and wasn’t known for his patience, waited several months to end things with Mary and pursue Anne?

In my opinion, therefore, it is highly likely that Henry Carey was not the son of Henry VIII.

And what does all of this mean? Well, as Ives put it in his biography, by 1526, when the relationship between Henry and Anne was in full swing, Anne had a broken betrothal, a failed romance and a flirtation with a poet to her name. That the next man in her life was the king of England was, needless to say, a surprise to many.