Finding love and companionship is difficult for everyone, but it becomes even more challenging when the future of nations rests on your shoulders, as a new Mail podcast explores.
The latest miniseries of the Queens, Kings and Dastardly Things podcast, hosted by historian Kate Williams and royal biographer Robert Hardman, uncovers the cutthroat world of royal matchmaking.
The first episode focuses on serial womaniser Henry VIII, whose pursuit of a male heir led to a trail of broken marriages, severed heads, and shattered alliances.
Long before the age of filters, people could still be duped by a particularly flattering portrait – as Henry VIII discovered when he agreed to marry the German princess Anne of Cleves.

Long before the age of filters, people could still be duped by a particularly flattering portrait – as Henry VIII discovered when he agreed to marry the German princess Anne of Cleves
The Worst First Date in Royal History?
Following the tragic death of his third wife, Jane Seymour, in childbirth, Henry VIII was once again in the market for another queen.
As the pool of eligible candidates was small – they had to be royal, virginal and Protestant – Henry’s advisors assembled a series of portraits of European princesses for the King to peruse like a catalogue.
Having been painted by some of the finest artists from the Continent, these portraits could be highly misleading, as Kate Williams explained.
‘There could be a disconnect between portraits and reality’, the historian told the podcast.
‘They may not have had filters in Tudor times, but they had something much more powerful – artistic genius.
‘One such artist was Hans Holbein, who produced beautiful images of princesses who were perhaps a little more ordinary.
‘It was his skill that led to the most disastrous date in royal history, a real epic fail.’
When an advisor presented Henry VIII with a portrait of Anne of Cleves, a Protestant princess from Düsseldorf, he was initially unimpressed by what he saw.
Despite the lukewarm reaction, she ticked most of the King’s boxes, so Henry instructed Hans Holbein to travel to the princess and paint a new portrait for a proper assessment of her beauty.

Holbein returned to Hampton Court Palace with a ‘splendid’ likeness of Anne, and satisfied, Henry agreed to marry her

The King would famously describe Anne as a ‘Flanders mare’ – comparing his new wife to a work horse

In July 1540, a mere nineteen days after Henry’s marriage to Anne was annulled, he would wed 19-year-old Catherine Howard
Holbein returned to Hampton Court Palace with a ‘splendid’ likeness of Anne, and satisfied, Henry agreed to marry her.
Wanting to appear flirtatious and catch a glimpse of his new bride, Henry planned to disguise himself and board Anne’s boat, now docked in England.
‘Henry’s cunning plan would prove a total disaster’, Williams said.
‘He goes into Anne’s bedroom and embraces her. Anne doesn’t recognise Henry at all – she thinks he’s a servant or a courtier.
‘Henry doesn’t like this. He thinks he’s God’s gift to women in every way and expects any woman who sees him to almost faint with surprise and wonder at his brilliance and virility.
‘Henry believes his majesty should be obvious to everyone – and the fact Anne mistakes him for a man, not a King, is so injurious to his ego, he can never forgive her.
‘On top of this, Henry notices that Anne has a very appealing lady in waiting, a young Catherine Howard.
‘Anne is swiftly told that the marriage should be annulled and should not be consummated.’
The King would famously describe Anne as a ‘Flanders mare’ – comparing his new wife to a work horse.
In July 1540, a mere nineteen days after Henry’s marriage to Anne was annulled, he would wed 19-year-old Catherine Howard.
Despite suffering the sting of a King’s rejection, what happened to Catherine shows Anne may have dodged a bullet.
Catherine would be beheaded two years later, on trumped up charges of adultery and treason.
To hear more stories like this one, search for Queens, Kings and Dastardly Things Now – available wherever you get your podcasts.