 During his first marriage to Catherine of Aragon , Henry conducted an affair with Mary Boleyn , Catherine 's lady @-@ in @-@ waiting . There has been speculation that Mary 's two children , Henry and Catherine Carey , were fathered by Henry , but this has never been proved and the King never acknowledged them as he did Henry FitzRoy . In 1525 , as Henry grew more impatient with Catherine 's inability to produce the male heir he desired , he became enamoured of Mary 's sister , Anne , then a charismatic young woman of 25 in the Queen 's entourage . Anne , however , resisted his attempts to seduce her , and refused to become his mistress as her sister Mary Boleyn had . It was in this context that Henry considered his three options for finding a dynastic successor and hence resolving what came to be described at court as the King 's " great matter " . These options were legitimising Henry FitzRoy , which would take the intervention of the pope and would be open to challenge ; marrying off Mary as soon as possible and hoping for a grandson to inherit directly , but Mary was considered unlikely to conceive before Henry 's death ; or somehow rejecting Catherine and marrying someone else of child @-@ bearing age . Probably seeing the possibility of marrying Anne , the third was ultimately the most attractive possibility to the 34 @-@ year @-@ old Henry , and it soon became the King 's absorbing desire to annul his marriage to the now 40 @-@ year @-@ old Catherine . It was a decision that would see Henry reject papal authority and initiate the English Reformation . 
