The Mediterranean Exile Meets the Canadian Heiress: A Royal Origin Story
Prince Philip did not arrive in England as a man of means; he was a homeless prince with a tattered suitcase and a lineage that offered more baggage than bank notes. People don't think about this enough, but his early years were a chaotic scramble across European borders. By the time he reached his late teens, his sisters had married German aristocrats and his mother was institutionalized. He was adrift. Then came 1938. In the posh, high-society circles of London and the coastal escapes of the South of France, he encountered a vivacious, blonde woman whose energy matched his own abrasive wit. That woman was Osla Benning.
Defining the Spark: Why Osla Benning Stood Out
She was not a royal. Because she was a Canadian heiress—born in Montreal but raised in the upper echelons of British society—she possessed a freedom that Philip found intoxicating. The thing is, Philip was always a bit of a rebel, and Osla, with her dark-rimmed eyes and a reputation for being the life of every party, was the perfect foil for a young naval cadet looking to plant roots. Where it gets tricky is determining exactly when the friendship turned into a romance. Contemporaries noted that whenever they were in the same room, the atmosphere changed. It wasn't just a casual flirtation; they were inseparable during his shore leaves from Dartmouth, often seen dancing at the 400 Club in Leicester Square.
The Social Landscape of Pre-War Britain
The issue remains that the British establishment was a rigid, unforgiving beast. Philip was an outsider. Even though he was a Prince of Greece and Denmark, he was seen as "German" or "stateless" by the old guard (a prejudice that would later haunt his courtship of Elizabeth). Osla, however, didn't care for such pedigrees. She saw a man who was blunt, handsome, and remarkably lonely. Their relationship thrived on a shared sense of humor—the kind that cuts through the stifling boredom of debutante balls and formal dinners. They were two young people living on the edge of a world about to catch fire, and for a brief window, they were each other's entire universe.
Beyond the Fairytale: The Depth of the Philip and Osla Romance
When we look at the timeline, the evidence is overwhelming. Philip spent his 1939 Christmas with Osla’s family, a move that in the 1930s was the equivalent of a public declaration of intent. But then, the Second World War erupted, pulling them apart just as things were getting serious. He went to sea; she went to a factory. Yet, the letters never stopped. If you dig into the memoirs of their mutual friends, like Sarah Baring, it becomes clear that Osla was the person Philip thought of while he was stationed on the HMS Valiant. Was it a deep, soul-shattering love? Honestly, it's unclear if Philip was capable of that kind of vulnerability so young, but he was certainly devoted. He even gave her a silver vanity case, a luxury he could barely afford on his modest naval pay, which she cherished for years.
A Codebreaker’s Heart and a Sailor’s Ambition
While Philip was navigating the Mediterranean, Osla was doing something far more secretive: she was working at Bletchley Park. This wasn't some vanity job for a socialite; she was a talented linguist translating German teleprinter traffic. Imagine the irony. Here was the man who would eventually represent the pinnacle of the British Empire, writing love letters to a woman who was actively cracking the codes of the very nation his sisters had married into. Their bond was forged in the crucible of wartime uncertainty, which explains why the intensity of their connection lasted for several years. It wasn't a fleeting summer fling, but a multi-year engagement of the heart that survived torpedoes and blitzes.
The Geographic Distance and the Emotional Toll
War changes people. It hardens them. As Philip rose through the ranks and witnessed the Battle of Cape Matapan in 1941, his letters to Osla became his only tether to a civilian life he barely remembered. But the long stretches of silence between them took a toll. We're far from it being a simple case of "absence makes the heart grow fonder." In reality, the distance allowed other influences to creep in—specifically the machinations of Lord Mountbatten, who had much grander plans for his nephew than a marriage to a Canadian commoner, regardless of how charming she was. Mountbatten was a man of cold calculation, and he knew that for Philip to truly "arrive," he needed a bride with a crown, not just a trust fund.
The Mountbatten Factor: Strategizing the Heart of a Prince
Lord Louis "Dickie" Mountbatten was the ultimate puppet master. He looked at Philip and saw a vessel for his own ambition. The question of who was Prince Philip’s first love was, to Mountbatten, an inconvenient detail that needed to be managed out of existence. He began orchestrating "chance" encounters between Philip and the young Princess Elizabeth as early as 1939, but the real push happened during the mid-war years. That changes everything. Philip was being pulled in two directions: the genuine, easy affection he felt for Osla and the monumental, history-altering duty being dangled before him by his uncle. It was a choice between a life of relative normalcy and a life of perpetual walking two steps behind.
The Comparison: Osla Benning vs. Princess Elizabeth
Comparing the two women is like comparing a wildfire to a hearth. Osla was unpredictable, witty, and worldly; Elizabeth was shy, dutiful, and had been sheltered her entire life. It is often argued by biographers that Elizabeth fell in love with Philip at thirteen, but Philip’s feelings were far more complex. He was twenty-one, a man of the world, while she was still a girl in pigtails. Is it possible to love two people at once? Experts disagree on Philip’s emotional capacity, but the letters suggest he kept Osla on the "back burner" even as his visits to Windsor Castle became more frequent. The contrast was stark—with Osla, he could be Philip the sailor; with Elizabeth, he had to be Philip the Prince.
Why the Establishment Preferred the Princess
The issue remains that the Palace wanted stability. In the aftermath of the Abdication Crisis of 1936, the last thing the British monarchy needed was another royal marrying a "foreigner" or someone without a title, even if she was from the Commonwealth. Osla was simply too vibrant, too "loud" for the buttoned-up courtiers of the era. They saw her as a distraction. As a result: the pressure on Philip to sever ties with his Canadian love interest became a matter of national interest. He was a man with no home and no money; the prospect of becoming the consort to the future Queen of England was an offer that no ambitious young man, no matter how much he liked a girl from Montreal, could easily refuse.
Alternative Theories: Were There Others Before Osla?
Before we settle entirely on Osla Benning, we have to look at the fringes of Philip's youth. Some historians point to Cobina Wright Jr., an American actress and debutante Philip met in Venice in 1938. She was arguably the most beautiful woman of her generation, and Philip was reportedly "obsessed" with her for a few weeks, even following her back to London. But was it love? No. It was a infatuation—the kind of red-blooded pursuit you'd expect from a seventeen-year-old prince with a roving eye. Cobina didn't take him seriously, eventually returning to the States and leaving Philip to nurse a bruised ego until Osla entered the frame and provided the emotional depth Cobina lacked.
The Brief Shadow of Hélène Cordet
Then there is the complicated case of Hélène Cordet. She was a childhood friend from his days in France, and rumors have swirled for decades that their bond was more than platonic—some even going so far as to whisper about the paternity of her children. Yet, most serious researchers dismiss this as gossip. Hélène was a confidante, a sister figure in a life where he had no stable female presence. The distinction is vital because it highlights Philip’s desperate need for belonging. He sought out women who reminded him of the stability he lost when his family collapsed. Osla Benning provided that stability during the war years, making her the first woman to truly hold his heart in a way that wasn't merely transactional or fleeting.
Common Misconceptions Surrounding Prince Philip's First Love
The Myth of the Greek Childhood Sweetheart
We often assume a royal exile like Philip would have found solace in a youthful Greek romance before his departure for Britain. The problem is that his early years were characterized by frantic movement and familial instability rather than domestic tranquility. Because he was shuffled between France, Germany, and the United Kingdom, the notion of a local Mediterranean darling is purely fictional. Historical records from 1930 to 1934 confirm he was largely under the guardianship of the Mountbattens. He didn't have time for a steady Greek flame. His life was a series of packed trunks and boarding school dormitories. Let's be clear: the romanticized "girl back home" simply did not exist for a prince who no longer had a home to return to in Athens.
Confusing Infatuation with Protocol
Another frequent error involves conflating his early friendships with the many debutantes he met at the 1937 coronation of King George VI. People love to speculate that every dance partner was Prince Philip's first love, yet most were strategic introductions orchestrated by his uncle, Lord Mountbatten. Was he actually smitten with every aristocrat in the room? Hardly. Most of these interactions were superficial. He was a penniless prince with high social standing but zero liquid assets. As a result: many historians mistake his natural charisma and "viking" looks for genuine romantic intent. We must distinguish between the social gymnastics of the 1930s London season and the actual stirring of a young man’s heart.
The Cobina Wright Jr. Diversion
The most persistent misconception involves the American actress Cobina Wright Jr., whom he met in Venice in 1938. While they spent three weeks together, the issue remains that this was a summer dalliance, not a foundational romance. He was only 17 years old. She was a rising star in the United States. And though he supposedly kept her photo for a time, she eventually married a wealthy American businessman in 1941. The intensity of this episode is often exaggerated by biographers looking for a cinematic prequel to his life with Elizabeth. It was a flirtation, not a life-altering bond.
The Expert Perspective: The Shadow of Osla Benning
The Canadian Heiress at Dartmouth
If we want to find the true candidate for Prince Philip's first love, we have to look at Osla Benning. They met in 1939. She was Canadian-born and possessed a wit that matched his own sharp tongue. She wasn't just another name on a dance card. Throughout the early years of World War II, Benning was the woman he corresponded with most frequently. Which explains why many of his contemporaries viewed her as the primary contender for his hand before the King's daughter became the obvious choice. They shared a sense of humor that was often described as "wicked." (Even the most stoic royals need a partner who can laugh at the absurdity of the court). This relationship survived the physical distance of his naval service in the Mediterranean and the Indian Ocean.
The depth of their connection is evidenced by the 1943 Christmas card he sent her from the HMS Wallace. He was already being scouted by the palace, but his letters to Osla remained affectionate and frequent. This was a relationship of shared experiences during a global crisis. Unlike his brief encounter with Cobina, his time with Osla spanned several years of his formative early twenties. Yet, the pressure of his royal destiny eventually eclipsed this private affection. By 1944, the trajectory toward the future Queen was set in stone. Osla remained a fond memory, but she was the casualty of a much larger geopolitical chess game.
Frequently Asked Questions
How did Osla Benning react to the engagement of Prince Philip and Princess Elizabeth?
Osla Benning reportedly handled the news with remarkable grace and a touch of realism regarding the royal hierarchy of the era. She eventually married John Henniker-Major in 1946, just a year before the royal wedding took place at Westminster Abbey. Sources from the time suggest she remained on friendly terms with the Prince, even though the romantic nature of their bond had to be permanently severed. Data indicates she lived a private but successful life, passing away in 1974 at the relatively young age of 53. Her family has generally remained discreet about the specific contents of the letters Philip sent her during the war.
Did Prince Philip have any serious relationships while stationed in Australia?
During his time in the Pacific toward the end of World War II, Philip was a young naval officer with a reputation for being socially active in Sydney and Melbourne. However, by 1945, his commitment to Princess Elizabeth was already becoming an open secret within high-ranking naval circles. While rumors of "Australian blondes" persisted in gossip columns for decades, no credible evidence or documented Prince Philip's first love candidate emerged from this period. His focus was primarily on his duties aboard the HMS Whelp and his impending return to England. The narrative of a wild colonial romance is largely a product of tabloid imagination rather than historical fact.
Was there ever a possibility that he would choose love over the Crown?
The choice was never quite that simple because Philip was a man of intense duty and limited options. As a displaced royal with no kingdom, marrying into the British Royal Family offered him the stability and purpose he had lacked since his childhood flight from Greece in a fruit crate. To walk away from a future Queen for a private romance would have been seen as a betrayal of his lineage and his benefactor, Lord Mountbatten. Historical analysis of his correspondence suggests he was pragmatic about his romantic life. He understood that his biological heritage demanded a specific type of union, and he leaned into that role with total commitment after 1946.
The Verdict on Philip's Heart
Searching for Prince Philip's first love requires us to look past the stiff-upper-lip exterior of the Duke of Edinburgh and see the displaced teenager of the late 1930s. We have to stop pretending that 1947 was the beginning of his emotional history. He was a man who experienced profound isolation, and his early romances were attempts to anchor himself in a world that had stripped him of his title and home. While Cobina Wright was the glamour, Osla Benning was the reality. But the true love of Philip’s life was arguably the role he eventually stepped into, a position that demanded he bury these early flames in favor of a 73-year partnership. It is ironic that a man so famous for his outspoken nature had to be so incredibly silent about the women who occupied his heart before the bells of Westminster rang. We might never see the full collection of his private letters, but the evidence points to a young man who loved deeply before he learned to serve. He was not a cold machine of state, but a veteran of emotional upheaval who found his final port of call in the monarchy.