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Author Reveals Why Meghan’s First Weekend With Harry’s Friends Was a ‘Nightmare’: 'She Lacked...'

Meghan, Duchess of Sussex, and Prince Harry, Duke of Sussex, watch the sitting volleyball competition on day 2 of the Invictus Games 2020 at Zuiderpark on April 17, 2022, in The Hague, Netherlands. (Cover Image Source: Getty Images | Max Mumby/Indigo)
Meghan, Duchess of Sussex, and Prince Harry, Duke of Sussex, watch the sitting volleyball competition on day 2 of the Invictus Games 2020 at Zuiderpark on April 17, 2022, in The Hague, Netherlands. (Cover Image Source: Getty Images | Max Mumby/Indigo)
Aug. 31 2025, Published 12:45 PM. ET
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In the early days of his relationship with Meghan Markle, Prince Harry was determined to introduce her to the world he had grown up in. What he didn’t anticipate, however, was just how poorly that first encounter with his closest circle of friends would go. According to royal biographer Tom Bower, the Duke of Sussex was branded 'nuts' by his old pals after he invited Markle to a traditional country weekend, as the gathering descended into what some later described as a 'nightmare.'

Prince Harry, Duke of Sussex and Meghan, Duchess of Sussex attend a Family and Friends Tubing event during day three of the 2025 Invictus Games. (Image Source: Getty Images | Samir Hussein)
Prince Harry, Duke of Sussex, and Meghan, Duchess of Sussex, attend a Family and Friends Tubing event during day three of the 2025 Invictus Games. (Image Source: Getty Images | Samir Hussein)

Harry had chosen Sandringham for the occasion, a place where shooting parties were a staple of royal life. For Prince William and Harry, who had grown up with the sport, these weekends were familiar, marked by long afternoons outdoors, banter over meals, and heavy drinking. Harry expected his American girlfriend to fit right in. Instead, Bower claims, the visit exposed a clash of worlds. “Harry was looking forward to endless banter, jokes, and a lot of drinking,” Bower wrote in his book Revenge: Meghan, Harry and the War Between the Windsors. “He had not anticipated Markle’s reaction.”

The actress, according to his account, did not take kindly to his friends’ humor. Bower alleged, “Without hesitation, Markle challenged every guest whose conversation contravened her values. According to Harry’s friends, again and again, she reprimanded them about the slightest inappropriate nuance. Nobody was exempt. Harry’s world would not be her world.”

Prince Harry, Duke of Sussex, and Meghan, Duchess of Sussex are seen on April 23, 2025, in New York City. (Image Source: Getty Images | Raymond Hall)
Prince Harry, Duke of Sussex, and Meghan, Duchess of Sussex are seen on April 23, 2025, in New York City. (Image Source: Getty Images | Raymond Hall)

As per Royal Insider, the pushback unsettled Harry’s old crowd. Many of the guests, most of them old Etonians accompanied by wives and girlfriends, felt Markle was a 'dampener on the party.' Bower described the post-weekend reaction as, “She lacked any sense of humor... Driving home after Sunday lunch, the texts pinged between the cars. ‘OMG what about HER?’ said one; ‘Harry must be f*****g nuts’; and ‘She’s a total nightmare’ were others.”

It was a turning point. As Harry grew closer to Markle, he gradually began to distance himself from friends who had long defined his bachelor years. Royal writer Angela Levin has noted that one of those who drifted away was Tom Inskip, once one of Harry’s closest companions and a fellow partner in youthful escapades, including the infamous 2012 Las Vegas trip that ended with Harry photographed naked during a strip billiards game, the BBC reported. 

Prince Harry and Meghan Markle at the Royal Pavilion during an official visit to Sussex on October 3, 2018. Image Source: Getty Images | Karwai Tang
Prince Harry and Meghan Markle at the Royal Pavilion during an official visit to Sussex on October 3, 2018. (Image Source: Getty Images | Karwai Tang)

“Harry was distancing himself from his old friends,” Levin wrote, suggesting that Markle’s uneasy reception in his inner circle contributed to the shift. Some of his pals, she added, had been skeptical about his relationship from the start. Other royal commentators agree that Markle’s values jarred with Harry’s old world. Tom Quinn, another author, recalled what one of Harry’s friends told Fox News, “'I can’t understand what Harry sees in her. She’s a tree hugger. She’s so woke.'” But Quinn also pointed out that this was exactly what Harry found compelling. “I think Harry was, in a way, entranced by the fact that Markle was able to offer him an alternative world from the one he’d always known.”

Prince Harry and Meghan Markle meet staff and volunteers during a visit to One25. Image Source: Getty Images|  Toby Melville - WPA Pool
Prince Harry and Meghan Markle meet staff and volunteers during a visit to One25. (Image Source: Getty Images| Toby Melville - WPA Pool)

Markle, who rushed into the wedding with Harry in turn, reportedly didn’t warm to Harry’s crowd either. Quinn described another Sandringham shooting weekend where Markle bristled at the politically incorrect jokes. “She hated it because all of Harry’s friends were making the sorts of jokes that suggested they disliked everything to do with ‘woke.’ They just don’t like that kind of thing because, to a large extent, it’s seen as Left-wing.”

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