The moment Prince Harry's Eton friends realised Meghan Markle would be trouble - as they whispered the royal was 'nuts' to be dating 'woke' spoilsport
Following Harry's decision to step down from royal duties in 2020 and move to California with Meghan, he has lost touch with many of his old associates.
The prince is now said to be lonely on the other side of the Atlantic, with his best friend now reportedly being his long-time security guard.
Prior to Megxit, Harry's oldest and closest pals were from his days at Eton College.
But the friendship circle first got distant after they met Meghan and she 'reprimanded' them over jokes they made about transgender people and feminism, according to a book.
Following the episode, the alarmed pals whispered Harry was 'f***ing nuts' to be dating the actress who they said acted 'princessy', 'woke' and had no sense of humour.
Here MailOnline looks back to the shooting weekend when Harry's old Etonian friends first realised Meghan would be trouble.
Following Harry's decision to step down from royal duties with Meghan in 2020 and move to California he has lost touch with many of his old friends. Pictured: Harry and Meghan on a walk in October 29, 2018
Shooting has been a long-time hobby for the prince and he was looking forward to joking around, bantering and drinking with his closest friends in November 2017. Pictured: Harry out shooting on the Sandringham Estate in 2009
Prince Harry and friends, including Tom 'Skippy' Inskip (centre right) attend the wedding of a mutual friend on September 14, 2013
Shortly after Harry's relationship with Meghan was revealed in November 2016, the duke invited 16 of his friends to a shooting party at Sandringham.
Shooting has been a long-time hobby for the prince and he was looking forward to joking around, bantering and drinking with his closest friends.
With the Queen's permission, the party descended on the 20,000-acre Norfolk estate, which has some of the finest shooting locations in England, along with their wives and girlfriends.
Most of the crowd were old Etonians and were all 'bonded by common assumptions, principles and loyalties', according to Tom Bower in his 2022 book Revenge: Meghan, Harry And The War Between The Windsors.
The plan was to meet for dinner on Friday night, go out shooting on Saturday, and leave after lunch on Sunday.
Bower writes in the bestselling book: 'He had not anticipated Meghan's reaction.
'Their jokes, involving sexism, feminism and transgender people, ricocheted around the living rooms and dining rooms.
'Without hesitation, Meghan challenged every guest whose conversation contravened her values.
With the Queen's permission, the party descended on the 20,000-acre Sandringham Estate (pictured), which has some of the finest shooting locations in England, along with their wives and girlfriends
Prince Harry sneaks away from a Royal shoot at Sandringham to light up a cigarette
The prince was regularly taken shooting as a boy. Pictured: Harry and Charles take part in a shoot at Sandringham on November 30, 1996
Prince Harry with friends Tom Inskip, Charlie van Straubenzee, and Thomas van Straubenzee at a 2015 Rugby World Cup semi final match at Twickenham in October 2015
Mr Bower, who claims to have heard about the episode from Harry's friends, wrote: 'Again and again she reprimanded them about the slightest inappropriate nuance. Nobody was exempt.'
The gang concluded Meghan was a dampener on the party and beyond Harry's hearing, they questioned her 'wokery'.
The seasoned biographer, who has previously published works on Richard Branson, Jeremy Corbyn and Boris Johnson, continued: 'Driving home after Sunday lunch, the texts pinged between the cars: "OMG what about HER?" said one; "Harry must be f---ing nuts."
'"She's a total nightmare" said others. Besotted, Harry was unaware of his friends' reaction.'
The Sandringham shooting party was not the only episode that alarmed Harry's friends to the potential trouble that Meghan could bring.
Four months later in March 2017, a similar gang travelled to Jamaica for the wedding of one of Harry's closest and oldest friends, Tom 'Skippy' Inskip to flame-haired literary agent the Hon Lara Hughes-Young.
Around 40 guests had gathered for the three-day party at the Round Hill Motel in Montego Bay, with Harry playing the role of one of the ushers in the service.
The shooting weekend alarmed Prince Harry's old friends from Eton. Pictured: The Duke of Sussex and Meghan, Duchess of Sussex in New Zealand on October 29, 2018
Harry and Meghan attend the wedding of his friend Charlie Van Straubenzee on August 4, 2018
Meghan greeting Harry's friends at the wedding of his school pal Charlie Van Straubenzee on August 4, 2018
Tom 'Skippy' Inskip (pictured with Harry in 2013 at a wedding in King's Lynn) is one of Prince Harry's oldest friends, but reportedly fell out with the duke after advising him to take things slow with Meghan when the pair first began dating
The close-knit group went so far back that 'all the parents in attendance fondly remembered giving Harry cottage pie and comfort during his teenage years', writes Mr Bower.
The gang 'keenly anticipated' meeting Meghan but were disappointed.
It is alleged some friends said Meghan quibbled about the food and was 'princessy', while refusing to engage with Harry's friends.
One mother told Mr Bower: 'She wasn't interested in us.'
And for her part, it seemed the feeling was mutual on Meghan's side, as she 'disliked Inskip and his crowd'.
'Their jokes and their attitude towards the world were unacceptable to her', wrote Mr Bower.
The two high-profile disasters sent alarm bells ringing around the group, and over the following weeks Harry's friends agreed he was rushing too fast towards marriage, claims the book.
Several shared their fears with William, who echoed the concern. He mentioned to his younger brother he had known Kate for eight years before he proposed.
But the appeal fell on deaf ears, Mr Bower wrote: 'Furious about the closing of ranks, Harry told Meghan. Both agreed that they were victims of racism. William, fumed Harry, was a snob.'
According to the biography, Finding Freedom, Skippy (pictured with his wife at Harry and Meghan's 2018 wedding) had a falling out with Prince Harry after he shared his 'doubts' about Meghan before they became engaged
Among those caught in the fallout was Harry's old Etonian pal Skippy, whose father Owen has been long-time friends with King Charles.
Harry and Skippy went back a long way, as it was he who accompanied the prince on his ill-fated trip to Croatia in August 2011, when they got drunk on vodka, whisky, beer and tequila, and were photographed jumping into a pool fully clothed at a nightclub on the party island of Hvar.
And he was with Harry during his trip to Las Vegas in 2012, when the prince was photographed naked during a game of 'strip billiards'.
Party-animal Skippy was once photographed driving a convertible sports car naked in the US with his modesty only preserved by the steering wheel.
He was also with Harry when he was seen inhaling 'hippy crack', otherwise known as laughing gas, at a party in 2010.
But the long and colourful history did not protect the friend from Harry's rage, and the two apparently fell out after he warned the prince against marrying Meghan.
According to the Sussex-friendly book Finding Freedom, Skippy expressed doubts about how quickly the relationship was moving and decided to warn Harry.
He is believed to have advised Harry and Meghan to live together before 'doing anything more serious.'
The royal couple have cut a more isolated figure since they moved to California following Megxit. Pictured: The pair on a royal tour of New Zealand
A source close to Sussexes told the book's authors that although his advice 'came from a good place,' Harry 'didn't totally see it that way'.
As a result, Mr Inskip and his wife Lara were reportedly 'punished' by being excluded from Prince Harry and Meghan's wedding party at Frogmore Cottage.
However, it has since been suggested that the two have made up following the birth of Prince Archie and the death of Tom's mother-in-law, although they now live on different continents.
It is not known if Skippy flew over for Harry's 40th birthday party in September, which was organised as a 'lads' holiday' mountain retreat in California with his 'closest mates'.
The guestlist has been kept a secret, but there is little doubt his birthdays were a far larger affair before he met Meghan.
