Signs Prince Harry And Chelsy Davy Were Never Going To Last

Before they would officially start dating in 2004, Prince Harry had already met Chelsy Davy. At the time, according to "William and Harry: Behind the Palace Walls," a book by royal expert Katie Nicholl, Davy had been in her final year at Stowe School in England. The pair met through a mutual friend, Simon Diss, who thought "they would make a good match."

Nothing happened then, however, seeing as she was about to graduate and move back to South Africa. Still, by all accounts, Harry seemed smitten with her from the start, so it was probably unsurprising that he had "every intention of reconnecting with her," according to Nicholl, when he left the Australian outback for Africa in his gap year.

During his time there, Harry would visit her frequently, their relationship growing more serious the better they got to know each other. At one point, according to Angela Levin's book "Harry: Conversations with the Prince," he even wrote to a school friend calling Davy "the love of my life — this one's unreal." By the time that summer ended and the prince had to return to England, he promised it would not be long before they'd see each other again. But were they always doomed to fail?

Chelsy Davy didn't care that he was a prince

In his memoir, "Spare," Prince Harry talks about how Chelsy Davy had seemed "different" to him since their first meeting. The feeling had only been reinforced when they saw each other again in Cape Town.

According to Harry, "Unlike so many girls I met, she wasn't visibly fitting herself for a crown the moment she shook my hand. She seemed immune to that common affliction sometimes called throne syndrome." This was something that seemed to pleasantly surprise him, as the prince says he had always wondered what it would be like to meet a woman interested in getting to know him, beyond just his title.

"Not only was she uninterested in my title, she seemed bored by it. 'Oh, you're a prince? Yawn,'" he said, adding that back then, Davy knew nothing about his family. The problem, of course, was that it was much easier for her to not care about his title when they were in Africa, getting to know each other in secret and away from the press. Harry told the court during his 2023 phone hacking trial, "At least one of my girlfriends told me she was warned off me by her parents saying, 'Is it really worth all the aggravation?'" not long before they broke up (via The New York Times).

She just wanted to be a normal kid

When you know more about Chelsy Davy's upbringing in Africa, it is easy to see how royal life was never going to be an easy fit for her. In a conversation with The Times, she talked about having grown up barefoot and surrounded by wildlife and being held at gunpoint in Cape Town. Still, it was trying to get used to the constant attention of the press that she found most difficult.

"It was so full-on, crazy and scary and uncomfortable," she said. "I found it very difficult when it was bad. I couldn't cope. I was young, I was trying to be a normal kid, and it was horrible." 

At the time, Davy had been trying to build a career, keeping busy and working long hours. Naturally, when she had the time, she wanted to go out with friends, only for pictures of her leaving bars to be plastered all over the tabloids the next morning, painting her as nothing more than a party girl.

Their whole relationship suffered tabloid interference

According to Prince Harry's lawsuit against Mirror Group Newspapers, he believes that constant harassment from tabloids was to blame for his disagreements with Chelsy Davy when they were together, and ultimately led to their breakup. As he sees it, even before they were official, the press had made up their mind about who he was in their narrative, and anything that seemingly went against that persona was something they'd try to manipulate.

In his witness statement, the prince said: "I always felt as if the tabloids wanted me to be single, as I was much more interesting to them and sold more newspapers. Whenever I got into a relationship, they were very keen to report the details but would then, very quickly, seek to try and break it up ... " Not only that but during the time they were together, Harry claims the tabloids often knew where they would be, even when that information was top secret.

He also said: "We were never on our own and able to enjoy each other's company away from the prying eyes of the tabloids." So much so, in fact, that the couple began to grow suspicious of everyone around them, finding it hard to know who to trust and confide in. This invasion of privacy has had long-lasting repercussions, with Harry saying, "Of course, now that we know that this information was invariably obtained by unlawful means, these friendships were lost entirely unnecessarily, which is a matter of huge regret for me."

Prince Harry didn't want her to change to fit into the Firm

When describing his first meeting with Chelsy Davy in Cape Town, Prince Harry said in his memoir, "Unlike so many people I knew, she seemed wholly unconcerned with appearances, with propriety, with royalty." 

Being such a well-known public figure, Harry seemed to find Davy's nonchalant attitude toward his status a refreshing change of pace. But, as it turned out, the very thing that originally drew him to her would eventually become a great source of reservation.

In "Spare," the prince recalls a conversation he had with his friend Teej, who asked if he saw them eventually marrying. Reflecting on Davy's distinctly different lifestyle and carefree attitude, he wrote: "She wore short skirts and high boots, danced with abandon, drank as much tequila as I did, and I cherished all those things about her ... but I couldn't help worrying how Granny might feel about them. Or the British public. And the last thing I wanted was for Chels to change to accommodate them." Despite their clear affection for each other, these concerns did not lessen over time, ultimately playing a part in their breakup. 

Harry was afraid the press would take someone else he cared about

Whether or not the British press actively tried to break them up, the fact remains that their constant presence added a lot of strain to their relationship from the start. From the moment they arrived in the U.K. together as a couple, in fact, Harry says they were hounded by paparazzi. In his witness statement in June 2023, he told one story of picking her up from the airport: "I walked into the arrivals hall with a baseball cap on and immediately spotted five separate paparazzi sitting on benches with cameras in bags, their hands inside rucksacks and everyone else looking at me."

He tried to normalize things for Davy, writing in "Spare": "I'd advised Chelsy to treat it like a chronic illness, something to be managed. But she wasn't sure she wanted to have a chronic illness."

Harry told her he understood if that was how she felt, of course, but that this level of exposure was a huge part of what being with him entailed, adding: "Thereafter, I put the chances at 50-50, maybe 60-40, I'd ever see Chels again. Odds were, the press would cost me another person I cared about." At the time, the prince recalls trying to manage his expectations by telling himself he didn't really have time for a relationship, so it would be fine if she decided to end things. 

King Charles III did not approve of their relationship

In royal expert Katie Nicholl's book "Harry: Life, Loss, and Love," she says Prince Harry finally introduced Chelsy Davy to his father, then-Prince Charles, and Camilla, during a Valentine's Day visit in 2005. Per her book, they seemed to really like her, with Nicholl claiming she was "such a hit" they invited her to come along on their annual family ski trip. Davy reportedly declined, with Nicholl writing that "her presence would only encourage the paparazzi."

This visit, however, came after a tabloid piece published in January of that same year claiming that King Charles didn't necessarily support the relationship. According to Harry's witness statement in 2023, "The article reported that I had 'slammed the phone down' on my father and included a quote from a 'senior aide' that described me as being 'incandescent' when my father described my relationship as 'puppy love' and that I had 'exploded' ... "

This article, written by Dean Rousewell, was published as a royal exclusive in the British tabloid The People. While it is impossible to know how much of the report was true, it is notable that Harry does not deny that there was a disagreement.

The two had many ups and downs while he was in the army

Among many other details of their relationship that went on to become public, quite a few paint a picture that his time in the army was very tumultuous for their relationship. For one, Prince Harry had wanted to be stationed in Iraq at the time, something for which Chelsy Davy shared no enthusiasm. He said in his testimony that while the tour was a possibility, she "was extremely worried, and we discussed it a lot" (via The New York Times).

Despite her concerns, the prince was still determined to serve, though a published tabloid piece in Sunday People reportedly mentioned that in one of their arguments, Davy had "begged him not to be a hero." In his witness statement during the phone hacking trial, Harry seemed convinced that the media's coverage ultimately interfered with his deployment.

Harry recalled a particularly difficult conversation in his memoir, stating: "What were we doing? Where were we heading? She knew I cared about her. But she felt unseen." There were also reports of Davy getting mad at him for going to strip clubs with his army friends, and even a breakup in 2007 after she found out he had flirted with another woman though, of course, that didn't last long.

Prince Harry wasn't sure Chelsy Davy was 'the one'

Aside from his concern about what his grandmother, the late Queen Elizabeth II, might think of his then-girlfriend's carefree personality, Prince Harry also said he wasn't sure if Chelsy Davy was "the one." Harry recounted in "Spare" that he told his friend, "It takes a certain kind of person to withstand the scrutiny, Teej, and I don't know if Chels can handle it." He wasn't certain that he even wanted to ask that of her, which is unsurprising, given that the meddling and attention were such a constant point of contention throughout their relationship. 

"When she was back in Cape Town she phoned me and said people were tailing her everywhere and it was driving her crazy. She couldn't imagine how they always knew where she was and where she'd be," he recalled. 

Not for the first time, she brought up not being sure about all the attention, or withstanding a lifetime of it. She wanted him to do something about the press attention, but all he could do was apologize. For his part, Harry could understand her desire for freedom. He stated that though he would miss her, "If I had a choice, I wouldn't want this life either."

They were deluding themselves that it could work

By 2010, the pair was back together once again, and Chelsy Davy attended Prince Harry's pilot course graduation at the Army Aviation Center in May. Their reconnecting didn't last very long, because as Prince Harry wrote in "Spare," they "had all the same old problems, nothing had been solved." Before he was expected to return to Afghanistan, they went on one final holiday to Botswana.

There, his friend Teej once again helped him look at their relationship more clearly. Harry wrote: "It's over, kids. You're postponing the inevitable. And making yourselves crazy in the process." 

He wrote about sitting in his friend's garden for this conversation: "She urged us to let this breakup be final. Don't waste the most precious thing there is. Time." The prince admits in his memoir that, during this trip, the two of them were being "willfully delusional" that things could still work out between them. It is clear, then, that their break up was less due to a lack of feelings, and more so because they ultimately wanted different things in life.

Prince William and Princess Catherine's wedding convinced Chelsy Davy they'd been right to call it off

Though they were no longer together at the time, Chelsy Davy was still invited to attend Prince William's wedding to Princess Catherine. According to Angela Levin in "Harry: Conversions with the Prince": "A friend revealed that seeing the enormity and pomp of the day convinced her that she and Harry had been right to separate. ... it could never have worked, especially as she valued her privacy and guarded it so carefully."

Katie Nicholl also reiterated this claim in "Harry: Life, Loss, and Love," writing that "being part of the royal wedding had made Chelsy's mind up once and for all. The life of a royal bride was not for her ... "

Despite the lifestyle differences that ultimately led to their breakup, the pair shared one last tearful goodbye over the phone in the week leading up to his wedding to Meghan Markle. In 2022, Davy married Sam Cutmore-Scott, a schoolmate of Harry's from Eton College, shortly after the couple welcomed their first son, Leo.