When Prince Harry announced his engagement to Meghan Markle in November 2017, he hoped the Royal Family would share in their happiness. However, his grandfather Prince Philip offered a blunt response, cautioning, “One steps out with actresses, one doesn’t marry them.”

In his revealing book “Entitled,” Andrew Lownie discusses Prince Philip’s hesitations about Meghan, the star of the TV show “Suits,” joining the royal family. These feelings may not come as a surprise, given Harry and Meghan’s whirlwind romance that lasted just 16 months before the proposal.

Royal biographer Ingrid Seward, in her book “My Mother And I,” notes that Prince Philip was among the few who remained skeptical of Meghan, then 44, during the early phase of her relationship with Harry, 41.

Additionally, Prince Philip reportedly found it “uncanny” how Meghan reminded him of Wallis Simpson, the American socialite for whom King Edward VIII famously abdicated the throne. As a result, he affectionately nicknamed Meghan “DOW,” after Wallis, the Duchess of Windsor.

Philip was also said to have thought it was ‘uncanny’ how much she reminded him of Wallis Simpson – the American socialite who King Edward VIII abdicated to marry.

As such, the prince nicknamed Meghan ‘DOW’ after Wallis, the Duchess of Windsor.

Philip also wasn’t the only royal to have attempted to caution Harry about the pace of his relationship with Meghan, with his brother, Prince William, said to have felt ‘nervous’ about their upcoming nuptials.

In January 2023 Harry discussed William’s warning to take it slow in his memoir Spare, writing: ‘”It’s too fast”, he’d told me. “Too soon”. In fact, he’d actually been pretty discouraging about me even dating Meg.’

When Prince Harry told Prince Phillip of his plans to marry Meghan Markle, he was issued a stern warning: ‘One steps out with actresses, one doesn’t marry them,’ according to royal biographer Andrew Lownie

However, Harry dismissed his family’s concerns, with it claimed that he believed he had to marry her quickly because her ‘biological clock was ticking’ as she was almost 35 years old, according to royal author Tina Brown.

Despite their fairytale wedding in May 2018, the Sussexes love story quickly took a sharp turn when the duchess realised that the life of a princess was far from what it was made out to be in the books.

After making the decision to withdraw from royal duties and relocate to North America in January 2020, later dubbed ‘Megxit’, Philip’s views towards Meghan were said to have soured further.

According to Seward, he simply couldn’t understand why Meghan was unable to follow his own example after marrying into the royal fold.

Speaking to Sky News in 2020, Seward explained: ‘I think he’s very, very disappointed because I think he feels he gave up his naval career in order to stand by the Queen and help the monarchy.

‘And why can’t Meghan just give up her acting career, support her husband and support the monarchy?

‘He just cannot understand why she couldn’t support Harry and help him rather than wanting to have her voice.’

After becoming the Duke of Edinburgh, Philip gave up his birth citizenship, his naval career and even his surname. In many ways he accepted that his life would be spent in the shadow of Queen Elizabeth II.

After Meghan and Harry took the decision to leave the Firm and the late Queen had called a summit in Sandringham to try to resolve the crisis, Philip was said to have been reluctant to be part of the talks

Philip also wasn’t the only royal to have attempted to caution Harry about the pace of his relationship with Meghan, with his brother, Prince William, also said to have felt ‘nervous’ about their upcoming nuptials

Seemingly indicative of his adverse feelings towards Meghan, after the pair took the decision to leave the Firm and the late Queen had called a summit in Sandringham to try to resolve the crisis, Philip was said to have been reluctant to be part of the talks.

The Duke of Edinburgh – along with Kate Middleton and Camilla – did not attend the meeting between the Queen, the then Prince Charles, Prince William and Harry to discuss the pair’s future role within the Monarchy.

The reason for Philip’s noted absence, Seward claimed, was that the duke simply wanted to wash his hands of the whole sorry affair.

She added: ‘Of course, it irritates him hugely. And when they had the Sandringham Summit, Prince Philip was seen leaving the house very swiftly before they all arrived.

‘He simply doesn’t want to get involved any more.’

Yet Philip’s concerns for Meghan’s suitability are likely to have been rooted in past experience, with the Suits star certainly not the first Hollywood actress to have entered the royal fold and caused quite the stir.

Aged 21, former prince Andrew Mountbatten Windsor began a relationship with American actress Koo Stark after the pair met on a blind date at the beginning of 1982.

Stark, then aged 24, later recalled how the two became ‘instantly inseparable’. 

According to royal biographer Ingrid Seward writing in her book My Mother And I, Philip was ‘one of the very few wary’ of being charmed by Meghan, 44, in the early days of her relationship with Harry, 41

Harry dismissed his family’s concerns, with it claimed that he believed he had to marry Meghan quickly because her ‘biological clock was ticking’, according to royal author Tina Brown

While a seemingly unlikely pairing – their budding relationship continued through to April when Andrew then left to serve in the Falklands War. 

The loved-up pair continued speaking throughout the conflict, with Koo, who travelled to Balmoral with a pair of pink plastic cowboy boots, patiently waiting to meet Andrew at the royal residence upon his return that September – unbeknown to the late Queen. 

‘When the Queen got to the back door she stopped in her tracks, pointed majestically at a pair of fluorescent boots and demanded: “Whose are those?”

‘They were quickly replaced by some green wellies from Ballater,’ Lownie writes. 

But rather than a mere fling, ‘it was clear that this was a serious relationship’.

Later reflecting on her daughter’s time with the now disgraced ex-duke, Stark’s mother, Kathi Norris, revealed that the two ‘talked about spending the rest of their lives together’. 

‘I thought they were going to get married,’ she said.

While the couple sought to keep a low profile for a while, news of their budding relationship eventually hit the press – with Stark likening the incessant press intrusion to ‘being under house arrest’. 

Aged 21, Andrew Mountbatten Windsor began a relationship with American actress Koo Stark after the pair met on a blind date at the beginning of 1982

Their relationship deteriorated – with Stark feeling ‘let down that Andrew accepted the situation instead of fighting for her’

For a while, the pair met in secret – using singer Steve Strange’s home in Chelsea as a location for their rendezvous under the alias of phrases such as ‘It’s the changing of the guard.’ 

But their relationship ultimately hit a crisis point. While Andrew was said to have sought to ‘persuade’ the Queen’s press secretary, Michael Shea, to release a statement asking that the couple have privacy – Shea refused, arguing that it was not the Palace’s place to comment on ‘private matters’. 

Stark had also felt ‘let down that Andrew accepted the situation instead of fighting for her,’ Lownie wrote.

The actress sought to evade the increasing public attention by travelling to Australia, Bali and India, but on her return to London in 1983, their 18-month whirlwind romance had lost its spark and the pair soon separated.

‘By then it was basically over… It wasn’t like a Hollywood movie, with a grand finale. In the end, we just ran out of energy. It had been strangled to death,’ Stark recalled.

After witnessing first-hand Andrew’s unsuccessful relationship with Stark and the public fallout, a wise Prince Philip was beginning to perceive distinct parallels emerging for Harry and his new lover, Meghan

Just three years later, Andrew wed Sarah Ferguson at London’s Westminster Abbey. The pair were given the titles of Duke and Duchess of York and had two children, Princesses Beatrice and Eugenie, but divorced in 1996. 

More recently, the ex-prince was stripped of his royal titles by his brother, King Charles, amid the ensuing fallout of his scandalous relationship with prolific sex offender Jeffrey Epstein.

Yet few may recall the wealth of public interest that once surrounded his relationship with the American actress and the undeniable lessons the Royal Family’s then-eldest member learnt from its quick demise.

Prior to his death in 2021, aged 99, Prince Philip was no doubt one of the wisest members of the Firm and was routinely favoured by his fellow family members as a valued counsel with direct honesty.

It seems unsurprising, therefore, that after witnessing first-hand Andrew’s unsuccessful relationship with Stark and the public fallout, he was beginning to perceive distinct parallels emerging for Harry and his new lover, Meghan.

As the old saying goes: ‘The only real mistake is the one from which we learn nothing.’

One can’t help but wonder how Harry’s relationship with his now estranged family may be today if he had heeded Philip’s warnings about Meghan all those years ago.