Isabel of Valois’ wedding, for all its royal pomp and circumstance, was the stuff of nightmares.

The occasion began with a thirty-two year old king and his thirteen year old betrothed. King Philip II of Spain would soon be head over heels for his young bride, despite being nineteen years her senior. Of course, the lovebirds wouldn’t meet until after their wedding. 16^th century sensibilities were unperturbed by missing husbands, and Isabel married Philip in a proxy wedding at the Notre Dame de Paris. Fernando Álvarez de Toledo, the forty-two year old “Iron Duke” of Alba, stood in for the absent king. Isabel took her arranged marriage and middle-aged pseudo-groom quite well, especially considering many of us at her age are deep in the throes of braces and middle school.

The wedding only worsened when Isabel’s father, King Henry II of France, thought he’d prove he could keep up with the kids in the celebratory tournaments. Like any doting father, Henry honored his newly-wed daughter with a round of jousting. Unfortunately, Henry picked the wrong opponent in his captain of the guard, the Duke of Montgomery. His eye was skewered with the duke’s spear and he suffered the injury for ten days before dying. The astrologer Gaurico would later boast having foretold the gruesome death, though in reality he had described Henry’s fate as “a most happy and green old age.” The only bright side to the wedding was the first meeting between Isabel and Sofonisba Anguissola, her future lady-in-waiting and art instructor. Unfortunately, making the acquaintance of a talented tutor doesn’t do much to distract from the pain of freak jousting accidents, especially when they’re in the family.

In Spain, Isabel would study under Anguissola, who enjoyed court favor to rival that of Anne Vallayer-Coster and Diego Velázquez. Not all of the queen’s friendships, however, would be so innocuous. Her relationship to the king’s son was of particular interest to court gossips, who found her unique gift for calming the volatile prince suspicious. The queen and king of Spain remained close, however, until she passed in 1568, and legend has it that her death date was the first and last day anyone saw Philip cry.