Inside Prince Harry’s ‘doomed’ romance with ex-girlfriend Chelsy Davy

The couple dated for several years on and off

Before Meghan Markle came along, Prince Harry had a number of relationships, including a long-term on-and-off romance with ex-girlfriend Chelsy Davy.

The Zimbabwean businesswoman and the future Duke of Sussex hit things off in the early noughties, before reportedly separating for good in 2010.
Chelsy and Harry were on and off for some years (Credit: SplashNews.com)

Prince Harry’s relationship with ex-girlfriend Chelsy Davy

Here is a look into their “doomed” relationship…

Chelsy Davy was Prince Harry’s first serious girlfriend. The two met while attending the Stowe School in Buckinghamshire. They went on to date for a number of years to follow.

The pair dated from 2004 to mid-2010 and things got pretty serious, with Chelsy even meeting the late Queen.
Harry was said to be attracted to Chelsy’s care-free nature (Credit: SplashNews.com)
Chelsy even attended Prince William and Kate Middleton’s wedding in 2011, following her breakup from Harry, resulting in a reunion with the prince that would unearth buried emotions.

Harry previously admitted his feelings following their separation in his tell-all 2023 memoir, Spare.

He discussed how it was reported that he “phoned Chels and tested some of the lines on her,” for his speech at William and Kate’s wedding.

The press claimed that Chelsy asked Harry not to reference “Kate’s killer legs” – a claim that Harry denies.

Prince Harry and Chelsy Davy’s ‘reunion’

“I never phoned Chels about my remarks; she and I weren’t in regular touch, which was why Willy checked with me before inviting her to the wedding. He didn’t want either of us to feel uncomfortable,” he penned.

“There were loads of feelings still there, feelings I’d suppressed, feelings I hadn’t suspected. I also felt a certain way about the hungry-looking men trailing after her, circling her, nagging her to dance,” he said. “Jealousy got the better of me that night, and I told her so, which made me feel worse. And a bit pathetic.”

Although the couple seemed to have a lot of fun together during their relationship, including several occasions where they were photographed rolling out of nightclubs, Queen Elizabeth II was reportedly not too fond of the match.

He wrote in his memoir that Chelsy made him “really happy,” but their future didn’t pan out.

Queen Elizabeth II’s alleged disapproval

“I couldn’t help what my grandmother thought about it. Or the people. And the last thing I wanted was for Chels to change to please them,” he wrote.

It seems that Harry wasn’t keen on Chelsy changing herself to fit into The Firm, especially as her care-free nature is what had attracted him initially.

Harry reportedly wrote in his memoir: “Unlike so many people I knew, she seemed wholly unconcerned with appearances, with propriety, with royalty.

“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.”

He went on to pen: “I’d always wanted to know what it might be like to meet a woman and not have her eyes widen at the mention of my title but instead to widen them myself, using my mind, my heart. With Chelsy, that seemed a real possibility. Not only was she uninterested in my title, she seemed bored by it. ‘Oh, you’re a prince? Yawn.’”

Chelsy’s difficulty in the public eye

Meanwhile, Chelsy has also opened up about the difficulty of being in the public eye.

“It was so full-on: crazy and scary and uncomfortable,” she told The Times in 2016. “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.”

Prince Harry more recently claimed the scrutiny of the tabloid press was the main factor in their split and such public criticism meant “a royal life was not for her”.

Why Harry’s relationship with Chelsy was ‘always set to be doomed’

In a written statement obtained by the New York Times in June 2023, during Harry’s lawsuit against the Mirror Group Newspaper Limited, Harry said his relationship with Chelsy “was always set to be doomed” due to “the prying eyes of the tabloids”.

“It was just that feeling of being under surveillance all the time,” he said.

“I believe Chelsy found this even more difficult to deal with when she lived in England… everyone has a limit as to what they can endure.”

Despite these challenges, a friendship between the pair seems to have lived on.

It was just that feeling of being under surveillance all the time.

In fact, the two pals were rumoured to have still shared a “strong” bond although Harry has since moved on with his wife, Meghan Markle.

Speaking to New Idea, a friend of the duke said that in 2020 a farewell party for Harry had been thrown by his friends, before he would step away from the royal fold for good.

Here, it was made clear, that Harry and Chelsy’s friendship was still going strong.
Chelsy Davy attended Harry and Meghan’s wedding in 2018 (Credit: SplashNews.com)

Harry and Chelsy’s friendship

The source claimed: “Harry was beaming when he walked into the room, and everyone was there waiting for him. He couldn’t believe his eyes when he saw Chelsy.”

They continued: “He gave her the biggest hug… She and Harry have a serious connection.”

The source added: “But I doubt they would ever hook up on anything.”

Chelsy also attended Harry and Meghan’s wedding two years prior, in 2018.

Unfortunately for her, she was snapped looking less than impressed during the ceremony, sparking headlines once more with many publications framing her as being jealous of Harry and Meghan’s fairytale romance.

Chelsy Davy at Harry and Meghan’s wedding

Reports claimed at the time that Chelsy had been “so emotional” about the phone call inviting her to the wedding that she almost didn’t attend.

“It was their final call, a parting call in which they both acknowledged Harry was moving on. Chelsy was quite emotional about it all, she was in tears and almost didn’t go to the wedding,” a source told Vanity Fair.

Chelsy has since moved on, marrying hotelier Sam Cutmore-Scott in 2022. They share a son and a daughter, Leo and Chloe.