 In 1526 , after eighteen years of marriage , Henry started to pursue the affections of Anne Boleyn , the sister of his former mistress , Mary Boleyn . At the same time , he became troubled by what became known as the King 's " great matter " , that is , finding an appropriate solution for his lack of male descendants . He found several possible options . He could have attempted to legitimise his illegitimate son Henry FitzRoy , but this would not be easy and would require the Pope 's intervention . He could have married his daughter Mary off and hoped for a grandson ; this was not seen as a real option , because Mary was a sickly child and was unlikely to conceive before Henry 's death . Finally , he could somehow reject Catherine and marry a bride more likely to bear children . Probably seeing the possibility of marrying Anne , the third was ultimately the most viable option to Henry , and it soon became the King 's wish to dissolve his marriage . 
