For much of their courtship, Prince Harry and Meghan Markle’s romance spanned an ocean. Although they are from different countries and radically different backgrounds—one a British royal, the other an American actress—modern travel and technology made their trans-Atlantic romance possible.

It wasn’t always so easy for royals to find matches—or even to see each other in the flesh before their wedding day. Until the advent of photography and advanced transportation, royals looking for a spouse had to rely on portraits and oral reports about their prospective mates. Marriage was a form of diplomacy, tying royal families together politically—often from afar.

“The prospective couple would often be in different countries, with marriage negotiations conducted by proxies,” explains Dr. Susan Foister, Deputy Director and Curator of Early Netherlandish, German and British Paintings at the National Gallery in London. “Portraiture was a vital tool to ensure that a stranger marrying into the royal line was sufficiently personable for royal status, and full-length portraits and full-face images were thought desirable, at least by the English, so any disfigurement could not be hidden.”

This was a big concern, as royal portraits supplied by the potential bride or groom’s own artist often exaggerated the attractiveness of the sitter. In 1795, the future Queen Caroline of England spoke for generations of disappointed royals upon first meeting her fiancé, the Prince of Wales. “I find him very fat, and by no means as beautiful as his portrait.”

Rulers were fully aware of the propaganda value of court portraiture (see, for example, artists’ attempts to soften and disguise the attributes of Spain’s Charles II, who lived with a number of physical issues as the result of inbreeding). To make sure the likeness of a potential mate was accurate, some European royals—almost exclusively male—resorted to sending their own trusted artists on missions to capture the likeness of their potential betrothed as early as the Middle Ages.

“In 1384, the French king [Charles VI]’s advisors sent an artist to Scotland to create an image of Egidia, daughter of Robert II, but before the painter arrived, she had already married a countryman,” historian Retha Warnicke writes in The Marrying of Anne of Cleves. “Artists next traveled to Bavaria, Austria, and Lorraine and, after viewing the miniatures they painted, 17-year-old Charles was said to have fallen in love with 14-year-old Isabella of Bavaria, whom he wed in 1385.”

In 1428, the legendary Flemish painter Jan Van Eyck traveled with a delegation to Iberia to contract a marriage between his patron Duke Philip the Good of Burgundy and Princess Isabella of Portugal. After the agreement was sealed for the couple’s betrothal, Van Eyck painted her portrait for Philip. According to art historian Linda Seidel, in her essay “The Value of Verisimilitude in the Art of Jan Van Eyck“, the now lost portrait provided “eyewitness testimony to the person of the princess so that when she arrived in Burgundy…there would be independent proof of her authenticity through the matching of her image to her person.”

But it was the entitled, obsessive Tudor kings of England who would send their chosen artists on a mad dash across the European continent. In 1502, the widowed Henry VII expressed romantic interest in Giovanna of Aragon, the dowager Queen of Naples. Not only did he want detailed first-hand accounts of her breast size, the smell of her breath, her drinking habits, and the amount of hair above her lips, he also instructed his ambassadors “to enquire for some cunning painter” to create a “very semblance” of her. The Queen refused to have her portrait painted, and Henry remained single.

His son, the legendary lothario Henry VIII, would go to extremes in his search for a royal wife he found physically attractive. “Henry VIII was looking for a fourth wife throughout 1538 and 1539, following the death of his third queen, Jane Seymour, in 1536,” Foister explains. He sent the master painter Hans Holbein, known for his exquisite, realistic portraits to royal courts all over Europe.

“Holbein always traveled with a professional diplomat from the court of Henry VIII, who would have been alive to all the political considerations,” Foister says, “so Holbein could just focus on his work of making an accurate portrait.”

First up was the enchanting and intelligent Christina of Denmark, a teenage widow who “was reported to be very attractive, with dimples when she smiled,” according to Foister. “A portrait by another artist had been sent to Henry, but it was not considered good enough, so Holbein was sent to Christina in Brussels in March 1538.”

On March 12, 1538, Holbein was given three hours to take Christina’s likeness. Holbein then hurried back to England to meet with the king. “We are told that on the day Holbein returned, March 18, 1538, the portrait of Christina he showed Henry pleased [the king] so much that it put him in a much better mood and he had musicians play on their instruments ‘all day long,’” Foister writes.

Marriage negotiations were slow—possibly due to Christina and her family’s wariness of Henry, who had already divorced one wife and beheaded another. However, this did not stop Henry from keeping the famous full-length portrait of Christina produced by Holbein, which is now in the collection of the National Gallery in London. Viewing it today, you can understand why it so captivated the king. Christina as painted by Holbein is a lovely, fresh-faced teenager, whose slight, wry smile hints at an intelligent, cultured character.

With no marriage contract in sight, Holbein was soon off again on a mission to paint other eligible royals, including Louise and Renee of Guise, Anne of Lorraine, and Marie of Vendôme. (If Holbein was able to obtain likenesses of any of these women, they are now lost.) Holbein was then dispatched to Cleves, to paint Anne and Amelia, the two sisters of the strategically important William, Duke of Cleves. Duke William, patriarchal and old-fashioned, was loathe to show his sisters to the English diplomatic party who begged for a better look, asking at one point sarcastically if the men “would see them naked?”

In August 1539, Holbein was finally granted permission to sketch Anne and Amelia. It is important to remember that artists working in foreign courts walked a delicate line—wishing to be accurate while not wanting to insult their hosts. “A portrait usually portrays the sitter as the sitter wished to be seen, perceived, and remembered,” writes art historian Sara N. James. “Think about how you perceive images of yourself, how you choose your Facebook profile portraits, for example.”

Holbein seems to have walked that line with finesse, as his two images—one miniature and one full-size—of Anne that survive attest. “English diplomats disliked the style of clothing and headdresses that Anne and her sister wore, calling them ‘monstrous’,” Foister notes, “and that in the miniature portrait (compared to the full-size one in the Louvre) Holbein seems to reduce the headdress in favor of emphasizing Anne’s face.”

It seems that Henry was pleased with both oral reports and Holbein’s portrait of Anne. A marriage contract was drawn up, and Anne made her way to England. However, not everyone was so convinced by Anne’s portrait. According to historian Allison Wier in The Six Wives of Henry VIII, a nasty little poem began to circulate in the English court:

_If that be your picture
__Then shall we
_Soon see how you and your picture agree.

The court’s cynicism was proven right. When Henry met Anne on New Year’s Day 1540, he was repulsed by her, crying out to his advisors, “I like her not.” However, throughout the ill-suited couple’s short marriage and divorce, it was not Holbein who met with Henry’s rage, but the king’s main advisor, Thomas Cromwell, leading one to speculate that the portraits were a fairly honest likeness.

Most likely, it was that indefinable something that draws couples to one another that was lacking, that indescribable feeling that no artist can capture or create. Henry VIII once shocked the French royal family by suggesting he meet with potential fiancées before a marriage was contracted. No doubt, Meghan and Harry would agree with that sentiment wholeheartedly.