Anne Boleyn meets and falls in love with Henry Percy of the Cardinal Wolsey retinue

The American historian Retha M. Warnicke writes that Anne was "the perfect woman courtier...

her carriage was graceful and her French clothes were pleasing and stylish; she danced with ease, had a pleasant singing voice, played the lute and several other musical instruments well, and spoke French fluently... A remarkable, intelligent, quick-witted young noblewoman... that first drew people into conversation with her and then amused and entertained them. In short, her energy and vitality made her the center of attention in any social gathering."
During this time, Anne was courted by Henry Percy, son of the Earl of Northumberland, and entered into a secret betrothal with the young man. Thomas Wolsey's gentleman usher, George Cavendish, maintained the two had not been lovers. It thus seems unlikely that their relationship was sexual.[39] The romance was broken off when Percy's father refused to support their engagement. According to Cavendish, Anne was sent from court to her family’s countryside estates, but it is not known for how long. Upon her return to court, she again entered the service of Catherine of Aragon.

Anne, however, had fallen in love with Lord Henry Percy, heir to the earl of Northumberland. They were secretly engaged and planned to marry. As Cavendish's account makes plain, Henry ordered Cardinal Wolsey to end the engagement. The Cardinal did so, thus earning Anne's lasting enmity.

Throughout history, people have wondered how and why Anne held out for so many years before surrendering to Henry. It must have been a challenge, as Henry was King of England, and a very persuasive suitor. Other women had succumbed to his charm and physical attraction. What made Anne behave so differently?

There are several possible explanations. One involves Anne's love for Henry Percy, a young man she met right around the time King Henry noticed her. Henry Percy was the son of the powerful Duke of Northumberland. Young Percy returned Anne's affections, and the two planned to marry, provided they could obtain their parents' permission. Henry Percy was a member of Cardinal Wolsey's staff, and saw Anne as often as possible when they were both at Court.

When Cardinal Wolsey found out about Anne and Henry Percy's plans, he refused to let them marry. Lord Northumberland, Percy's father, also forbade the match, claiming that he had planned to marry his son to the daughter of another high-ranking family. Both Cardinal Wolsey and Lord Northumberland felt that the Boleyns were not prestigious enough to be joined to the Percy family in marriage. It is not certain whether King Henry was behind this, or whether Cardinal Wolsey acted on his own. In any event, the marriage request was denied.

Anne Boleyn and Henry Percy were devastated when they heard the news. Percy was called back home and forced to marry the woman chosen by his family. Anne became bitter and angry, possibly for all her life, that she was denied her true love in marriage. It is not unlikely that she resented King Henry for his role in this, and held it against him for many years.

Anne Boleyn's first documented appearance at Court was at a masque, on 1 March 1522. In 1522, Anne Boleyn met and fell in love with a wealthy young noble called Henry Percy. Henry Percy was a member of the Cardinal Wolsey retinue. The were betrothed but the cuople were split up by Cardinal Wolsey. Henry Percy was forced into a loveless marriage and Anne never forgave Cardinal Wolsey.