If there was one element that impacted the psychological makeup of Edward VII more than any other it was the fact that he was a disappointment to his parents, Queen Victoria and Prince Albert. That’s not conjecture – it was something they took pains to verbalize to him, write to him and discuss about him to others. His complete and total failure to meet their exacting and lofty standards for a perfect prince and heir was so plainly understood by the entire Royal Family and the Queen’s government that it practically howls off the historical record.

But whatever the young Edward VII, or Bertie, was or wasn’t, his parents were uniquely cruel to him. In August 1861, Bertie was finishing up a summer at the military camp at Curragh in Ireland and his parents were visiting him there to see what he had accomplished. He hoped that he might show off his ability to command a company, but that was quickly set aside when a colonel told him, “You are too imperfect in your drill, and your word of command is not sufficiently loud and distinct.”

Days later, passages appear in Bertie’s diary that mark three distinct engagements at Curragh, dated on September 6, 9 and 10 – “N.C. 1st time, N.C. 2nd time, N.C. 3rd time.” This, my friends, is how the future Edward VII lost his virginity.

Now, lest you think this post has gone downright tawdry, may I instead remind you that the Victorian Era garnered its reputation the old-fashioned way. I wish that this post was a wholly unnecessary view inside a historical figure’s personal life – instead, it had a lasting impact on Bertie’s relationship with his mother and, God help us all (but especially his future wife), his relationship with women.

N.C. stood for Nellie Clifden, a woman who has been described as a great many things in the 150+ years since she found her way into the Prince of Wales’s bed, but was technically an “actress.” The brief sexual liaison came just as Bertie’s parents had decided it was time for him to marry. He was 19, but his elder sister, Vicky, had already married a Prussian prince, moved to Berlin and had two children. Arrangements were in the works for his younger sister, Alice, to marry another German prince the following year. And since he was the heir to the throne and the succession lay with him, then yes, his parents reasoned, it was time for him to settle down.

Beyond that, his parents thought a wife might force Bertie to mature. He had completely failed their academic regimen, the methods of which included beatings, solitary confinement and regular humiliation. He showed little to no interest in the subjects in which they demanded he show unique and earnest passion. He was not a scholar, not an intellectual or the human personification of perfection his parents believed could be reached if they approached parenting like a chemist trying to concoct a particular potion.

What he was was enormously kind, empathetic, a shrewd study of people and charming. He had all the makings of a politician or diplomat, if only he had the opportunity or the confidence. His parents, but especially his mother in later years, allowed neither. He also had a stubborn streak – and as he grew older, an obstinate independence. He took pleasure in the pastimes that would shock his parents – smoking, gambling and women. He knew he would never truly please his mother so he mostly stopped trying, only appeasing her when he directly needed her. If it was callous, it was a mutual callousness – it was a detachment Queen Victoria deserved based on the mothering she offered.

In short, he became the very thing by which his parents were most horrified – a London society darling.

First there was Nellie, but she was pivotal. She was the inverse of the sort of woman he would be expected to marry and formally socialize with, found for him by the sorts of friends his parents had tried to keep him from. In other words, perfection for a 19-year-old boy.

His parents were dangling German princesses before him, but he had discovered “actresses.” Desperate, they even showed him a Danish princess – less ideal for political reasons, but a genuine beauty who they thought might catch their son’s eye. Bertie was unmoved, uninterested in marriage and downright horrified by the idea of looming fatherhood.

That fall he wrote a letter to his friend Charles Carrington, which read:

“I hope that you will continue to like Cambridge […] and I trust that you will occasionally look at a book, which at present (entre nous) you have not much done. You won’t I’m sure forget those few hints I gave you regarding certain matters, and I have not forgotten those you gave me at the same time. I am glad to hear that our friend is in good health as I had not heard anything about her for some time […] P.S. You won’t I hope forget your promise not to show anybody any of my letters.”

Oh, in case you missed it from the Prince’s skilled games of stealth, that letter is about Nellie.

He continued to see her fleetingly throughout the autumn – rumor has it that on the occasion of his 20th birthday party he even snuck her into Windsor Castle. That last bit may have been one move too brash, because three days later a courtier came to Windsor and told Albert what his son was up to. And Albert, though he later told Bertie that he hadn’t, did in fact tell Victoria. They handled it as only they could.

Albert wrote a letter, noting that he was writing “with a heavy heart, on a subject which had caused me the deepest pain I have yet to feel in this life.” His version of giving his adult son “the talk,” included:

“To thrust yourself into the hands of one of the most abject of the human species, to be by her initiated in the sacred mysteries of creation, which ought to remain shrouded in holy awe until touched by pure and undefiled hands […] At your age, the sexual passions begin to move in young men and lead them to seek explanation to relieve a vague suspense and desire. Why did you not open yourself to your father? […] I would have reminded you [of …] the special mode in which these desires may be gratified […] by […] the holy ties of Matrimony.”

Note from me to you: I laughed out loud three times transcribing that.

Anyway, Bertie responded to his father’s letter with an earnest apology, though he refused to give up the names of his friends who had introduced him to Nellie. His father’s next letter read:

“You must not, you dare not be lost; the consequences for this country and for the world at large would be too dreadful! There is no middle course possible […] You must either belong to the good, or to the bad in this life.”

The following week, Albert visited Bertie at Cambridge and the two went for a man-to-man talk in the rain and stayed up hashing it out until 1 am. By the time Albert returned to Windsor, he was ill. He soldiered on through his work and engagements until December 7 when finally his physicians offered a diagnosis: Typhoid. He died on December 14.

Bertie was only summoned to his sickbed at the last minute by Alice, because his mother refused to write him. As Queen Victoria plunged into the depths of her mourning, she was unable to separate out her son from the last weeks of Albert life, blaming him for causing her husband pain, forcing him to make the trek to Cambridge and putting any of them in the situation of being the subject of gossip.

For years, Bertie’s brief affair with Nellie was referenced in letters by his mother to him, reproving him for it or using it as an excuse for why she was barring him from some activity or making a demand. It was brought up again and again as a way to humiliate Bertie – at one point she forced him to explain it to a third party and apologize. But the truly horrifying part of it was that Queen Victoria vehemently believed she was right in doing so. In her mind – indicative of the social world which she had created for herself – Bertie had quite literally been defiled, made less by an association with a prostitute.

Now, this is certainly not a defense of soliciting prostitutes, but the fact remains Bertie’s actions have to be considered in the context of his time. In an era in which men and women – but especially women – were expected to remains virgins until marriage, prostitution was by far more normalized. Affairs occurred, as they do now, but with women deemed “safe” – prostitutes and married women.

Whatever Bertie learned from the experience, it certainly didn’t scare him straight. He continued to “see” prostitutes and married women throughout his life, though our knowledge of the society matrons is more extensive. It’s an interesting response to a youth built on shame and harsh discipline – to what extent Bertie internalized any of it is anyone’s guess, but by all appearances he shunned his parents’ attitudes and teachings, at times going too far in the other direction.

You don’t need to be Freud to take a stab in the dark as to why, but the more interesting response is the extent to which his childhood appears to have emotionally hardened him. Once a sensitive child, he built a thick skin in adulthood that may have shielded him from the wounds of his mother, but also made him a lackluster husband, an absent father and an occasionally disloyal friend.

Edward VII is rarely given enough credit for what he did accomplish during his reign – and what he could have done had he had more time on the throne. Unfortunately, his woeful reputation from his “Bertie” years, captured in hysterical and excruciating detail by his mother, tends to drown out the man he could have or wanted to become.