Harry’s Ex’s Friend Called Their Breakup the ‘Best Thing That Ever Happened to Her’ Right Before Reports the Prince Saw Her as the ‘1 Person Who Really Understood’ Him
He may be royal, but the friends of Prince Harry’s ex-girlfriend, Chelsy Davy, weren’t a fan of their relationship.
An anonymous friend of Davy’s told the Daily Mail in November that the jewelry brand owner — who dated Harry from 2004 to 2011 — “has never been happier” than she is now with her husband, hotelier Sam Cutmore-Scott. The couple married in 2022 and shares two children: a son named Leo born in 2022, and a daughter named Chloe, born in 2024.
“It’s strange to think of the parallel life she would be living if she’d stayed with Harry,” the friend said. “But that was a long, long time ago. That break-up was probably the best thing that ever happened to her.”
As for the reason for Harry and Davy’s split, royal biographer and Majesty magazine Editor-in-Chief Ingrid Seward also told The Mirror in November that Davy broke up with Harry because of their different lifestyles. “She knew, as Cressida, did, that royal life just wasn’t for her. She was intelligent enough to see that from an early age,” Seward said, referencing Harry’s other famous ex-girlfriend, Cressida Bonas, whom he dated from 2012 to 2014.
She continued, “She wasn’t over-powered by ambition to better herself, or to marry into the Royal Family. At the end, she said to him: ‘There’s no way this is ever going to be my future.'” Seward also predicted that Davy would’ve “hated” moving to Montecito, California, where Harry lives now with his wife, Meghan Markle, and their two children, son Archie and daughter Lilibet.
Davy also confirmed that her and Harry’s lifestyle differences were part of the reason for their breakup in an interview with The Times in 2016. “It was so full-on: crazy and scary and uncomfortable. I found it very difficult when it was bad. I couldn’t cope,” she said of the relationship. “I was trying to be a normal kid and it was horrible.”
She explained that the media attention was one of the reason she moved back to her home in South Africa. “It was nuts,” she said. “That’s also why I wanted to go back to Africa. Now it’s calm, it’s fine.”
The comment from Davy’s friend came right before a source told Radar Online that Harry is “tormented by regret” over his marriage to Meghan as he watches Davy and Cutmore-Scott”s new life together. “He’s been unusually reflective, almost anguished at times. Hearing about Chelsy building this peaceful family life has hit him harder than he expected,” the insider said. “He keeps saying she was the one person who really understood the madness of his world.”
Another source added: “There’s this sense that he wonders what might have been if he hadn’t walked away from her. It’s become a recurring theme in his thinking – regret, nostalgia and the fear he made a series of irreversible mistakes.”
The insider also claimed that Harry has become “fixated” on his ex-girlfriend’s new life. “He talks about how uncomplicated things always felt with her. Watching her settle into this idyllic new life has stirred up all kinds of emotions – not least because his own situation in California is far from the fairy tale that was promise,” the source said.
Another insider added, “There are moments when he seems overwhelmed by the life he’s chosen – the scrutiny, the pressure, the relentless expectation that everything he and Meghan do must be monetized, plus her almost crazed desire to be a celebrity. It’s everything he wanted to escape when he quit the royal family. He now looks at Chelsy’s life and sees the road not taken.”
A different friend of Harry’s also told the website that the topic of Davy and her new husband has become “inescapable” in recent weeks. He’s not saying he wants to go back in time, but he’s deeply unsettled. It’s clear he’s wrestling with the choices that brought him here,” the insider said.