The “Spanish Match” as it has become known captures a bizarre and sophomoric jaunt from the future Charles I and George Villiers, Duke of Buckingham through Spain and France as they hunted for the next queen of England. The King of Spain’s sister, Maria Anna, was their target, but though the potential alliance went nowhere, they did in fact stumble upon Charles’s future wife – Henrietta Maria of France. The episode’s significance stems from the political impetus behind it, while its now infamy comes from the sheer ridiculousness of the scheme.

As the 1620s dawned, England was in fact without a queen following the death of Anna of Denmark in 1619. The widower James I was on the last leg of his reign, while his eldest son, Henry Stuart, had died back in 1612. His sole remaining child was thus his heir – Prince Charles – while his only surviving daughter, Elizabeth had married Frederick of the Palatinate in 1613. Elizabeth would end up known as “The Winter Queen” by history thanks to a brief stint as Frederick’s queen consort in Bohemia, but they – and their Protestantism – were driven out of power by the Catholic Hapsburgs in 1620.

Elizabeth begged her father and brother for military support, but James preferred a diplomatic approach. Specifically, he believed that arranging a marriage between Charles and Maria Anna of Spain would help encourage the Hapsburgs to withdraw, while an added bonus was the massive dowry she would bring with her, making James less dependent on Parliament (a recurring theme for our Stuart kings). To make the deal palatable, he would offer up an alliance against the French.

In 1621, James summoned Parliament and requested the necessary funding for a potential war with Spain…after all, the alliance only worked if the Hapsburgs believed war with England was a real possibility. But Parliament wasn’t particularly interested in their next king marrying a Spanish princess – in yet another indication for how the 17th century would play out, they instead demanded that Charles marry a Protestant. Offended by what he saw an encroachment of royal authority, James dissolved Parliament and forged ahead with marriage negotiations, blatantly flouting the advice of his ministers.

When the back-and-forth slowed, Charles, worried for his sister, decided to take matters into his own hands. By his side was his father’s “favorite,” George Villiers, Marquess of Buckingham. James’s sexuality has long been debated, but what is fair to say with certainty is that he maintained a series of male favorites that he kept close to him at his courts in both Scotland and England. Buckingham had first caught James’s eye in 1614 and, thanks to the support of courtiers eager to puppeteer access to the King, he soon positioned himself as the royal companion.

But James was growing older and Buckingham’s popularity with the King didn’t extend to the rest of his court. Thus, developing a relationship with Charles was paramount if Buckingham didn’t want to lose his influencer or, entirely likely, be charged with criminal offenses by Parliament after James’s death.

Charles’s idea was to travel to Spain in disguise and essentially take Philip IV by surprise, put his government on the spot and woo Maria Anna personally. Charles was 22, so the ridiculousness of this scheme can perhaps be chalked up to youth – James, on the other hand, should have known better and it remains a complete mystery how he allowed himself to be persuaded to sign on. Regardless, he did, and the two set off for the continent.

Their final destination was of course Madrid, but on their way there they stopped in Paris and visited the royal family at the Palace of the Louvre. There, Charles first came face-to-face with his future wife, Princess Henrietta Maria, then only 13 years old. If they made any impression on one another it’s been lost to history. The two men reached Madrid on March 7, 1623.

Philip IV of Spain was then just shy of 18, king for only two years and the de facto leader of a strict and ornate court that demanded a very particular brand of pomp and ceremony from its monarchs. The young King was shocked to learn the Prince of Wales had unceremoniously landed on his doorstep, but he also intrigued and went out of his way to show all due honor to the man that would eventually become his brother king. A personal meeting with Maria Anna was ruled out, but Charles and Buckingham were set up with their own household and given a suite of rooms in the Alcazar.

As spring turned into summer, the two men took full advantage of a busy court by attending masques, bullfights and games, and purchasing priceless works of art that would later become the cornerstone of Charles’s famous collection. In the midst of this, James elevated Buckingham from marquess to duke.

But the Englishmen, while celebrated, also scandalized their hosts with their familiarity. Buckingham’s proximity to the inner workings of the royal family had made him relaxed in their company – that, combined with their relative informality shocked the Spanish and in fact undermined Charles’s suit with the King’s sister.

As for the infanta herself, she had little interest in marrying a Protestant. Instead, Philip put the full court press on Charles to convert to Catholicism, a notion that angered and offended the Prince. The two left Madrid in October in a huff, and in complete failure despite the celebratory procession that greeted them when they returned to London.

Within two years James would be dead and Charles would be king. His wife would become another Catholic princess, Henrietta Maria, who was, ironically enough, Philip’s sister-in-law through his wife, Isabelle of France. Buckingham, meanwhile, would survive James’s death, but only just. He was assassinate in 1628, his death coming as stark relief to Henrietta Maria, who was no fan of the favorite.

As for Maria Anna, she went on to marry Ferdinand III, the Holy Roman Emperor. Bohemia very much stayed among their many titles.