Edward III and his wife, Philippa of Hainaut are best-remembered for their plethora of sons, but between them they also produced five daughters, the eldest of whom was Isabella of England. Believed to be her father’s favorite, Isabella was born at Woodstock Castle on June 16, 1332 and named for her paternal grandmother, Isabelle of France.

She joined in the nursery her elder brother and her father’s heir, Edward, and in 1334 they were joined by a younger sister, Joan. In youth, these three formed a slightly more senior trio of royal children as their mother continued to produce siblings at a regular clip. Surviving records detail opulent decorations, from fur blankets to silk wall hangings to jewel-encrusted clothing.

Considering royal women, particularly eldest daughters, were often betrothed as children, it would have been a fair assumption that Isabella’s actual time spent in England with her family would have been limited. Such was not the case: In 1335, when she was three, Isabella was betrothed to Prince Pedro of Portugal, but the arrangement fell through and he was later betrothed to Joan instead. In 1338, a second match was identified, this time with the Count of the Flanders’ eldest son, Louis. It, too, fell apart.

In 1340, the three children left the royal household to continue their education in the home of William and Elizabeth St Omer, a standard practice at the time, though it was less usual for brothers and sisters to make the transition together. Here, Isabella was in negotiations to marry Henri, eldest surviving son of John III, Duke of Brabant, in 1344, but it turned out to be yet another false start.

Three years later Isabella was 15 and Louis of Flanders, who had inherited his father’s title, circled back. The match was slightly more complicated by then because the pivotal Battle of Crecy had been fought between England and France resulting in an English victory and the death of Louis’s father. Reportedly, he was in no rush to wed the daughter of the man he held responsible for his father’s demise, but given Isabella’s favor with her father and the significant dowry she would bring with her, it was an offer he couldn’t lightly refused.

Well, that and Flanders and England maintained a mutually beneficial trading relationship and the Flemish people would be damned if their lord was going to pass up bringing home an English princess. Under immense pressure at home, Louis agreed to marry Isabella on March 1, 1347 at Bergues in northern France, with a wedding date fixed for the following month.

When a contract had been signed, Edward and Philippa held a celebratory hunt for the party that ended in Louis taking the opportunity to ride off, straight for the court of King Philip VI of France where he quickly married Margaret of Brabant (daughter of John III) that June.

Isabella was effectively jilted, which begs the question of why so many arrangements fell through and did she care? To be fair, princesses in her position were usually betrothed at least a few times during their childhood – as years passed waiting for the children to grow up the politic needs shifted and alliances that once seemed attractive lost their luster. The situation with Louis, while scandalous, could also be blamed on the consequences of Crecy, which Isabella had nothing to do with. So, to a certain extent, nothing was particularly amiss.

She wasn’t known to be a beauty – her hair and eye color were dark in a time when it was fashionable to be blonde and blue-eyed. Her complexion, which ideally should have been “fair” was described as “sallow.” Even so, her enormous wealth and the alliance with her father should have offset these drawbacks. It is worth mentioning, too, how incredibly spoiled the girl was becoming, her father’s clear favor of her over her sisters noticeable even from the driest of financial records.

Some of this had to do with Isabella’s status as the eldest unmarried daughter, but given how close she was in age to Joan, who was not shown the same appreciation, it remains marked. She maintained a posse of ladies-in-waiting and servants, more than three times the amount as Joan. She presided over tournaments and was fawned over at court – all in all, it was a pleasurable existence, so perhaps she could be forgiven for not particularly wishing to leave.

And apparently she didn’t. In 1351, now 19, she was again betrothed to Bernard, heir of Sieur d’Albret of Gascony. Given her status, it wasn’t a particularly lofty match, indicating it may have been Isabella’s preference or her parents’ wish to simply marry her off quickly – 19 being “old” by Medieval standards. In November of that year, five ships laden with her retinue and goods were provided to carry her to Gascony and at the last-minute Isabella refused to board, staunchly rejecting the proffered marriage.

No explanation was given, but bizarrely Edward doesn’t seem to have punished his daughter or publicly displayed any anger. Instead, she was given possession of her entire trousseau, including the money, lands and finery she had been gifted. Over the next few years, now an adult, she was given her own residence in London, a landed estate, manors and a new suite of rooms at Woodstock, her birthplace. Remarkably, she spent her 20s living the life of a single woman with independent wealth (well, to the extent that was possible).

In 1360, now 28, Isabella met Enguerrand VII, Lord of Coucy, a Frenchman brought to the English court as a hostage for King Jean II of France, a still-lingering consequence of the Battle of Poitiers five years before. At some point over the next few years, Isabella seemingly fell in love and, in fact, it’s quite possible they fell in love with one another. They were married at Windsor Castle on July 27, 1365 and were allowed to travel to France together that fall. The following spring, Isabella gave birth to her first child, a daughter christened Marie.

The next month the family returned to England and Edward, delighted to see his daughter and granddaughter, made Enguerrand the Earl of Bedford, in addition to his French titles. Isabella gave birth to a second daughter, named Philippa after her mother in 1367 and the couple soon returned to France.

Presumably Enguerrand expected Isabella to primarily remain with him in Coucy, or to follow him as he traveled to fulfill his military duties. Certainly that was the template that a number of royal and noble wives followed, including the wives of Isabella’s brothers. Isabella, on the other hand, returned to England every chance she could, usually without her husband. She seemed to have little interest in taking up the mantle of “wife” or mistress of his household and lands, and instead preferred the role of Edward’s favorite daughter.

Enguerrand, for his part, was in a politically sensitive situation given his French background and his English wife, and he sought to remain as politically neutral as was possible as the Hundred Years’ War carried on over the rest of the 1360s and 1370s. The couple traveled to England together in 1376 when Isabella’s elder brother, Edward, took ill and died, but the tide turned irrevocably when Edward III died in 1377, the English throne passing to his still-underage grandson, Richard II.

Enguerrand acted quickly and decisively to sever all of his ties with England. It’s likely that with his father-in-law gone he no longer felt beholden to honor his marriage or the gifts he had been given through their alliance – it’s also possible the timing allowed him to make final an unofficial separation that had already existed between him and Isabella. In any event, Enguerrand took their eldest daughter, Marie, and maintained a residency in Coucy, while Isabella stayed in England with their younger daughter, Philippa. While Enguerrand wrote to Philippa, he never saw her or Isabella again.

The only financial constraint placed on Isabella by her marriage was that her properties were held within a trust, but she was able to spend their income as she pleased.

Isabella died in the spring of 1379 and was buried at Greyfriars Church Newgate in London.

Enguerrande remarried to Isabelle of Lorraine in 1380 and had one more daughter before dying in Bursa while a prisoner of war in 1397.

Their daughter, Marie, married Henri of Bar, Marquis de Pont-à-Mousson in 1384 and had two sons before dying in France in 1405.

Philippa married a close friend of her cousin, Richard II, Robert de Vere, 9th Earl of Oxford in 1376, when still a child. In 1387 de Vere was granted an annulment and began an affair with a lady-in-waiting of Richard’s wife, Anne of Bohemia. Philippa’s uncles were livid and her mother-in-law sided with her, taking her into her household for protection. De Vere was exiled from England the following year and in 1389 the annulment was revoked by the Vatican. De Vere died in 1392.

When Richard II remarried Isabelle of Valois a few years after Queen Anne’s death, Philippa became an attendant and even followed her to France after Richard’s death. She died in 1411, likely having returned to England after Isabelle died in childbirth in 1409, if she hadn’t already.