In a public ceremony in June of 1525, with both Anne Boleyn and Henry's wife Katherine of Aragon in attendance, Henry VIII created his illegitimate son Henry FitzRoy, the Duke of Richmond. This title was last held by Henry's own father Henry VII, and by creating FitzRoy the Duke of Richmond, Henry was effectively preparing to have an alternate option as his heir to the throne. During Henry's nearly 20-year marriage to Katherine, only one of at least six attempts at pregnancy ended in a healthy, living child, the Princess Mary. That Henry so desperately wanted a male child to succeed him was to govern his thoughts for the remainder of his reign. England had only recently recovered from a very turbulent period of civil war called the War of the Roses. The last thing Henry wanted was any question as to the legitimacy of his heir. Technically, a woman was not barred from the throne and could rule in her own right. Unfortunately, the only example of this occurring ended in disaster, and the queen, Matilda, was disposed. With this in mind, Henry was convinced that if Mary should succeed him, it would be disastrous, and the best that could happen would be that she would marry a foreign prince and therefore bring England under foreign rule.

Of course, the ceremony must have been humiliating for Katherine to attend, since Henry was essentially saying that she had failed to produce a true heir. At this point, the difference in ages between the married couple were evident. Katherine was older, and more pious and sober minded than the gregarious and active Henry. Also, she was well past child-bearing years and Henry lost the affection that he had for her. To add to this feeling, Katherine was actually married previously to Henry's older brother, Arthur, who died soon after the marriage. Although it seems very likely that the marriage between Katherine and Arthur was never consummated, Henry began to feel that his marriage was cursed because he married his "dead brother's widow." In a section of Leviticus in the Old Testament it is said that "if a man shall take his brother's wife, it is an unclean thing... they shall be childless." Of course, Henry conveniently forgot his daughter in this statement, but it can be interpreted that Henry should not have married Katherine. In the midst of all this, he fell in love.

Anne Boleyn was caught quite by surprise by this turn of events, and at first was clearly shocked and not really able to respond to him. After all, he had only recently ended a long relationship with her sister! But Anne was clear from the start that she would never follow in her sister's footsteps. She replied to his urgings by saying, essentially, "Your wife I cannot be, both because of mine own unworthiness, and that you have a wife already. Your mistress I shall not be." Though the words may be spurious, the sentiment rings true. Anne would be Queen or nothing. That Henry's passion grew from a mild flirtation to something more significant is indicated by the 17 existing love letters that he wrote to Anne during the beginning part of their relationship. Henry was not a writer by nature, and that he wrote so frequently to Anne is a testament to the great desire and love he felt for her. The letters survive because at one point, they landed into the hands of the Vatican. Anne's responses to Henry are all lost, probably destroyed after her death.

Anne frequently left court to retire to Hever Castle, firstly to avoid the king and hope he'd give up, and then perhaps to entice him further into action when it became clear that absence did indeed make the heart grow fonder. When Anne was at court, she was still a lady-in-waiting to Katherine, and as the romance became common knowledge, a bitter rivalry between the two women began. But soon Anne was realizing the power she was beginning to receive, and all the jewels, attention and influence she was getting would have been hard to resist for long. As Henry became more deeply attached to Anne, Anne began to see that becoming Queen of England might become a real possibility... one that she couldn't pass up.

The differences between Henry's first and second wife are striking, and are similar to more modern examples of a man going through a "mid-life crisis." As stated above, Katherine was older than Henry, approximately 41 or 42 at the beginning of Henry's flirtation with Anne, and she was approximately 19 or 20. Anne was cultured, spirited and enjoyed many of the same passions as Henry, especially a love of music. Katherine, however, was increasingly turning to religion to help her through the pain and suffering of losing so many children. Katherine became dull and retiring, and increasingly became less and less like her husband. Since she could no longer bear children, Henry stopped visiting her bedchamber and went elsewhere. But Anne was refusing him, so the tension was becoming more and more intense. Had Anne given in, it is likely that she would not have been a real threat to Katherine, but Henry may very well have seeked divorce anyway. If he tried to marry a foreign princess, he may have had better luck getting an annulment. Yet Katherine was still powerful since she was the aunt of the most powerful man in the world, Charles, the king of Spain. When news of Henry's plans reached Katherine, she pleaded with her nephew for assistance. Since the annulment would have been a great slight to Spain, Charles was only too happy to oblige.

And so began the great stalemate called the "Great Matter." It was to last for almost seven years. Since Henry needed to seek the Pope's permission to get an annulment from Katherine, and since Charles effectively had control over the Vatican, Henry had a very long wait, indeed. The tension can be illustrated by a legend that occurred during this time. Apparently, Anne and Katherine were playing a game of cards. When it became obvious that Anne needed a king in order to win, and when she received one, Katherine proclaimed, "My lady Anne, you have good hap to stop at a king, but you are not like the others, you will have all or none." Anne, like Henry, had a long wait ahead of her, and the strain of the pressure of such a position was beginning to show. She became increasingly irritated at the lack of progression, and since Henry was relying on Wolsey to solve the situation, she couldn't resist trying to show Wolsey up as a failure to the king.

The time between Henry's pursuit of Anne and their eventual marriage almost seven years later was fraught with difficulty. Wolsey's initial attempts to seek a dispensation for the annulment were all fruitless, and Wolsey was falling further from Henry's regard, much to Anne's delight. She and her faction, or partisans, were beginning to see the political power Anne had, and Anne became bolder, suggesting that Henry read previously banned texts regarding politics and religious reform. That Henry listened to Anne is a testament to his attachment to her, and also that he was a king who was easily led. Trouble also came when Anne became seriously ill in June of 1528, with a disease called the Sweating Sickness. Henry was not willing to risk getting the disease himself by visiting her, but sent his best physician, Dr. Butts, to her aid. Fortunately for Anne, but not for Katherine, she survived. Further problems came when the Vatican was attacked by the Spanish in 1527, and while the English and French joined forces in aid of the Pope, in 1529, they were completely defeated. The result, of course was that the Pope couldn't possibly offend the Spanish king by divorcing his aunt from the king of England. In an effort to appear helpful, the Pope, through Wolsey's constant demands for action, sent Cardinal Campeggio, a papal representative, to England to hold a court ruling on the annulment. This hearing, the Trial of Blackfriars, began on May 31, 1529.

Both Henry and Katherine were required to attend the trial, with Anne hidden in the background, not seen. She was not supposed to have been seen publicly as any reason for the annulment, so she was kept away from the proceedings that were supposed to shape her future. When Katherine was called into court, she made a passionate plea, begging Henry on her knees not to proceed with the hearing, stating "I take God and all the world to witness that I have been to you a true, humble and obedient wife, ever comfortable to your will and pleasure... And when ye had me at first, I take God to my judge, I was a true maid, without touch of man. And whether this be true or no, I put it to your conscience." However, Henry's conscience was hardly worth appealing to, since he was determined to be rid of her. The trial continued, although it was obviously not going to be resolved, and Campeggio retired the proceedings until October 1; another stalemate for all involved. The person to suffer the most for this was Cardinal Wolsey, who assured the king and his "Lady" that the trial would be a success. On October 9, he was charged with preamunire, dismissed as the Lord Chancellor (Sir Thomas More replaced him), and sentenced to imprisonment. In disgrace and in poor health, he died a year later on November 29, 1530, narrowing missing trial and execution for high treason.

Now Anne had complete control over the king's inner thoughts. She helped advance two men who were to figure greatly in securing her marriage and also her downfall, Thomas Cranmer, her own family chaplain, and Thomas Cromwell, an unscrupulous lawyer who had served under Wolsey. It was Anne and Cromwell who suggested that change might only ever happen if Henry broke ties with Rome, and declared himself the Supreme Head of the English Church. Meanwhile Anne took out her frustration that Henry continued to see Katherine, berating him once by stating, "Did I not tell you that when you disputed with the queen she was sure to have the upper hand? I see that some fine morning you will succumb to her reasoning, and that you will cast me off. I have been waiting long and might in the meantime have contracted some advantageous marriage... But alas! Farewell to my time and youth spent to no purpose at all." What Anne was eluding to is that time was running out, and she might have had children by now, something meant to spur the king on to further action. In 1531, Henry finally left Katherine, taking Anne with him. Katherine continued to call herself queen, and indeed queen she was still, for Henry would take another two years before he finally broke with Rome and created the Anglican Church of England. In 1532, things came to a head.

The Archbishop of Canterbury died in August of that year, and remarkably, the Pope agreed to the placement of Thomas Cranmer in this role. Also, Anne took the huge step of allowing Henry to her bed, and around December of 1532, she became pregnant. This forced Henry to act, since the last thing he wanted was another illegitimate child. In 1533, things finally turned around.