To fill the vacancy at court, discussions were held regarding which princesses were available and what political benefits might be obtained. Henry is reputed to have suggested the cynical equivalent of a shape-up, all the potential princesses should be lined up at Dover and he would pick the one that best suited him.
The more usual alternative was to send the court painter to bring back a “true likeness” of the potential princesses. Hans Holbein set out on this task, and drew many of the potential candidates, each of whom for political reasons or because they married some other person, turned out to be unavailable. Meanwhile Henry feared his relations’ potential interests in taking his crown from him or his descendants, and there was widespread “taking to the Tower,” questioning and some executions.
Discussions continued around the question of the next queen, Holbein was sent to make a portrait of Anna of Cleves, Thomas Cromwell signed their marriage contract in October 1539, and in January 1540 Henry married her in his palace at Greenwich. From the outset he turned against her, there were varying excuses, none of which seems to have been supported, but she was dismissed from the court in June, and by mutual consent the marriage was annulled on the grounds of non-consummation in July of the same year.
Remarkably, once the ill-fated and ill-chosen match was dissolved, Henry and Anna became good friends. She was accepted at court, was on good terms with Mary and Elizabeth, and was given substantial properties. She outlived Henry and his subsequent wives, though she was only 41 when she died.