Before he met his now-wife, Meghan Markle, Prince Harry's longest relationship was his on-again, off-again romance with Chelsy Davy, which started in 2004 and ended in 2010. After their split, the exes have remained on good terms and Davy reportedly accompanied Harry as his plus-one to Prince William and Kate Middleton's royal wedding in 2011, the year after their breakup.
In the years since they ended things for good, both Harry and Davy have made it clear that royal life and the scrutiny that comes with being (or just dating) a member of the royal family was the primary reason for the split. Ultimately, Davy realized that it wasn't the life she wanted for herself, and if royal life wasn't right for her, then continuing a relationship with a prince just wasn't possible.
"She (Chelsy) knew, as Cressida [Bonas, whom Harry dated from 2012 to 2014] did, that royal life just wasn’t for her. She was intelligent enough to see that from an early age," royal biographer and Majesty magazine Editor-in-Chief Ingrid Seward told the Mirror of Davy's reasons for ending the royal relationship.
Prince Harry and Chelsy Davy kiss whilst sitting in the Royal Box as they attend the Cartier International Polo Match in July 2006 in Egham, England.
"She wasn’t over-powered by ambition to better herself, or to marry into the Royal Family," Seward added. "At the end, she said to him: 'There’s no way this is ever going to be my future.'"
And, according to those close to Davy, it's a decision that she doesn't second-guess—in fact, friends of hers recently told the Daily Mail that she "has never been happier" than she is now, with her husband, hotelier Sam Cutmore-Scott.
"It’s strange to think of the parallel life she would be living if she’d stayed with Harry," one of Davy's friends told the publication. "But that was a long, long time ago. That break-up was probably the best thing that ever happened to her."
Davy's aversion to committing to royal life was long-speculated to be the primary reason for the couple's split, and, in 2016, she confirmed as much during an interview with The Times.
Chelsy Davy and Prince Harry on a date documented by paparazzi in 2006.
"It was so full-on: crazy and scary and uncomfortable. I found it very difficult when it was bad. I couldn't cope," Davy said of dating Harry and the attention that came with the relationship. "I was trying to be a normal kid and it was horrible."
Davy, who is South African, said she returned to her home continent after the breakup to make a calmer life.
"It was nuts," she explained. "That's also why I wanted to go back to Africa. Now it's calm, it's fine."
According to Seward, Harry's decisions to step back from life as a working royal and to move to California wouldn't have been enough to salvage the relationship for Davy, long-term.
"She would have hated it all, especially the Montecito madness that is now Harry’s life," Seward predicted.