All the signs Prince Harry and Meghan Markle’s relationship was written in the stars: From an interview that confirmed Harry was ‘ready to find a wife’ to the Duchess’s royally good matchmaker friend

It’s common for couples to muse that the universe might have worked in a mysterious way so that they could meet.

And it seems likely to some that the chance circumstances of Prince Harry and Meghan Markle‘s first date met those requirements.

After all, he was a member of the British Royal Family living in Kensington Palace and she was an American actress living 3,500 miles away in Toronto.

Harry even claimed at their engagement interview in November 2017 that ‘the stars were aligned’ when they met, adding ‘this beautiful woman just sort of literally tripped and fell in my life’.

He had been looking for someone special, but up until the moment he bumped into Meghan, dating had been a bit of a disaster for him.

Despite his status as the most eligible bachelor in the country, the Prince’s love life included a series of failed relationships with an array of heiresses, airheads and aristocrats. 

His on-off relationship with Chelsy Davy petered out after seven years, his fling with the late Love Island host Caroline Flack bombed and his romance with The Saturdays pop star Mollie King fizzled.

His last serious relationship before he met Meghan, with the aristocratic model Cressida Bonas, also seemed to end in tears due to his hatred for the Press and angry tantrums.

Meghan Markle and Prince Harry made their public debut as a couple at the Invictus Games in Toronto in September 2017

Harry and Meghan pose in the Sunken Garden at Kensington Palace for their official engagement photo call on November 27, 2017

Meghan at the Polo Ralph Lauren VIP Suite at Wimbledon on July 4, 2016. She would go on her second date with Harry that night

Following the repeated failures, one expert claimed he started to feel like the ‘royal Bridget Jones’.

He was so exhausted by the constant dating that by 2016, at the age of 31, he finally felt ready to settle down and find a wife.

At that time his friends were already settling down and starting families, leaving Harry in danger of becoming the lone single figure at society events. 

He had seen his brother Prince William enjoying the simple pleasures of family life and wanted that experience for himself. 

The thirst for finding the one was so great that he candidly told TV presenter Denise van Outen at a birthday party in January 2016: ‘I’m not dating and for the first time ever I want to find a wife.’

Four months later, he brought up the subject of love and marriage again during an interview with The Sunday Times.

He told the paper: ‘At the moment my focus is very much on work but if someone slips into my life then that’s absolutely fantastic. 

At the couple’s engagement interview in November 2017, the Prince breathlessly gushed that ‘the stars were aligned’ when he met Meghan, adding ‘this beautiful woman just sort of literally tripped and fell in my life’

Prince Harry visits an NHS clinic to promote the importance of getting tested for HIV on July 14. He still seemingly had a smile on his face from when he met Meghan 11 days before

Before Meghan, Harry’s two most serious girlfriends had been Chelsy Davy (left in 2011) and Cressida Bonas (right in 2016)

Meghan at Wimbledon on July 4, 2016. Later that night, she went on a second date with Prince Harry, where she was given American-themed cupcakes to celebrate Independence Day

By 2016 Harry had seen his brother Prince William (pictured with Kate Middleton that year) enjoying the simple pleasures of family life and wanted that experience for himself

‘I am not putting work before the idea of family, marriage, all that kind of stuff. To be fair, I haven’t had that many opportunities to get out there and meet people.’  

Dating had been complicated for the Prince, as the royal expert Andrew Morton explained in his 2018 book Meghan: A Hollywood Princess.

Morton, who wrote the 1992 blockbuster biography Diana: Her True Story, which revealed Charles’s affair with Camilla, claimed Harry had found it difficult to find someone ‘willing to take [him] on’.

Whenever he was introduced to someone new, he always wondered whether they were attracted to him for his personality or his title? 

As one of his friends pointed out to the author: ‘You have to be a very special kind of girl to want to be a princess.’ 

But it seems Harry’s luck was finally changing, as unbeknownst to him, Meghan would be flying into London for one week that summer.

She was officially there to promote the upcoming season of her TV show Suits and to dress to impress at Wimbledon, where her sponsor Ralph Lauren held (centre) court.

But Morton believes that when Meghan landed at Heathrow Airport she had ‘love and marriage’ on her mind. 

Meghan stars as Rachel Zane in the hit American TV show Suits. It was on a trip to London to promote the show that she met Harry

Dating had been complicated for the Prince, as the royal expert Andrew Morton (pictured in 2019) explained in his 2018 book Meghan: A Hollywood Princess

The trip to the UK was one of many that Meghan had planned in her summer, when she wasn’t filming her time-consuming role in the legal drama in Canada. 

In her and Harry’s 2022 Netflix ‘docuseries’, her friend Lindsay Jill Roth said: ‘In the summer of 2016, [Meghan] had a few different trips planned. And she was just going to be free.’

Meghan said: ‘I was really intent on being single and just [having] fun girl-time.’

Another friend called Lucy Fraser told the documentary: ‘She had planned her single-girl summer and she had a lot of plans of going around Europe.’

It then cut to Meghan who said: ‘I had a career. I had my life. I had my path… and then came H. I mean, he literally, talk about a plot twist.’

The universe does indeed work in mysterious ways. 

When she arrived in London, Meghan began working closely with Violet von Westenholz, a Ralph Lauren PR executive.

It was Violet who organised Meghan’s marketing efforts on behalf of the fashion brand.

But Violet was not just a well-connected fashion expert – her family had royal connections going back decades.

Prince Harry’s childhood friend Violet von Westenholz chats to Meghan Markle at Wimbledon on July 4, 2016. Meghan had already arranged to go on a second date with Harry that evening after being set up by Violet

Meghan with Violet von Westenholz, together with Sadie Mantovani and Olivia Buckingham, at Wimbledon in June 2016, just before she was set up with Prince Harry

She had known Harry since they were teenagers through her father, the former Olympic skier Baron Piers von Westenholz, who is a close friend of King Charles. 

Over the years, Violet regularly travelled with her family to join the royals on skiing trips abroad, with Violet and her sister Victoria becoming regular fixtures among the Princes’ social set. 

At one time Victoria was even seen as a possible match for Harry, according to Morton.

What’s more, her mother, Jane von Westenholz, is a long-time friend of Queen Camilla, and in 2022 it was announced that the Baroness had been appointed one of her official ‘Queen’s Companions’. 

It seemed Meghan, too, was in need of Violet’s skills as a royally good matchmaker.

Meghan had married American film producer Trevor Engelson in 2011, but she ended things with him in 2013 ‘totally out of the blue’ by sending him his ring back in the mail, according to Morton. 

Not long after her divorce from Engelson was finalised in 2014, she began stepping out with Canadian celebrity chef Cory Vitiello.

Meghan’s two most serious relationships before Harry had been with producer Trevor Engelson (left) and celebrity chef Cory Vitiello (right) 

After the release of Prince Harry’s memoir Spare, a royal fan shared a clip of Meghan and Suits co-star Sarah Rafferty using a dog filter

It was her most recent relationship before she met Harry, and it lasted for two years.

There was talk of a possible engagement, but the pair are believed to have ended things just weeks before she met Harry, according to reports at the time.

So when Meghan met Violet on the publicity day for Ralph Lauren at Wimbledon in the summer of 2016, she was thankful to have met someone so important. 

She uploaded a photo on her Instagram with the PR director and other guests, captioning the post: ‘How much more could I adore this gem thank you Violet von Westenholz’. 

In Spare, Harry recounted how he fatefully first came across a video of Meghan on Violet’s Instagram and being immediately drawn to her ‘angelic face’ – despite the pair using a funny dog filter.

‘I’d never seen anyone so beautiful,’ he said, saying it felt like a ‘punch in the throat’ because of Meghan’s ‘wild joy’.

The Duke said the short clip stopped him in his tracks and he kept returning to it – before messaging Violet.

‘I sent Violet a message. ‘Who…is…this…woman?’ Harry wrote, before telling readers that she then linked him and Meghan together via Instagram.

Meghan then messaged Harry on the social media site, according to the memoir, before the pair exchanged numbers and eventually agreed to go on a first date.

The rest, as they say, is history.