Inside the Rollercoaster Relationship of Prince Harry and Chelsy Davy

Prince Harry was in a long-term, on-and-off relationship with Chelsy Davy before marrying Meghan Markle in 2018. The couple first met in 2004 in South Africa, shortly after Harry completed his studies at Eton College and before he embarked on his military training at Sandhurst.

"We had discussed the idea of hosting a dinner party, but there was a slight hitch - we didn't know anyone in Cape Town," wrote the Duke of Sussex in his memoir, Spare, published in January 2023. However, he recalled meeting a girl named Chelsy years ago at the Berkshire Polo Club in South Africa, and felt she could be the solution to their problem. Harry remembered Chelsy as unique and not preoccupied with superficialities, including his royal status.

She stood out from the other girls I had met, as she didn't seem to have a desire for a crown the moment we first met. She wasn't affected by the common condition known as throne syndrome, which was refreshing to see. I had always wished to meet a woman who was interested in me for who I am, rather than my title. Chelsy seemed to be that woman, as she showed no interest in my status and even seemed disinterested when I mentioned it. Our connection felt real and genuine. However, our relationship faced challenges when I was in the military, and we had to have difficult conversations about our future together. Despite my care for her, she felt unseen at times.

According to the Archewell cofounder's memoir, Spare, the duke and Davy ended their on-and-off again relationship for good in 2010 due in part to Davy's reservations about life in the public eye. The duke expressed understanding for Davy's reluctance to deal with constant scrutiny, acknowledging that it was not a lifestyle that everyone could handle. He respected her desire for freedom and did not want to pressure her into a situation that she was not comfortable with.

In Prince Harry's lawsuit against Mirror Group Newspapers, which took place more than a decade after his split with Chelsy Davy, their relationship was brought up. Harry claimed that the media company's alleged unlawful intrusions caused significant challenges in their relationship and led Davy to believe that a royal lifestyle was not suitable for her. Davy moved on with Sam Cutmore-Scott, whom she married in 2022 and shares a son named Leo with. On the other hand, Harry shares two children, Archie and Lilibet, with Meghan.

Keep scrolling for a look at Harry and Davy’s relationship timeline:

Credit: SplashNews.com

Prince Harry and Chelsy Davy’s Relationship Timeline: Split, Reunion at Prince William and Princess Kate's Wedding, More

Prince Harry had a romantic relationship with Chelsy Davy for a number of years prior to his marriage to Meghan Markle in 2018. The two first met in South Africa in 2004, when Harry had just completed his education at Eton College and was about to embark on military training at Sandhurst.

"We were discussing the possibility of hosting guests for dinner, but we faced a slight challenge - we didn't know anyone in Cape Town," recounts the Duke of Sussex in his memoir, Spare, published in January 2023. However, Harry soon recalls his acquaintance with a South African girl named Chelsy whom he had met years ago at the Berkshire Polo Club. "I remember her being unique," he writes fondly of the Zimbabwean native, describing her as someone who was "completely indifferent to appearances" and his royal status.

She stood out from the other girls I had met; she didn't seem to be seeking a crown the moment we met. She didn't suffer from the common affliction known as throne syndrome, as the BetterUp CIO noted. I had always wanted to meet a woman who wasn't impressed by my title but by my mind and heart, and with Chelsy, it seemed like a possibility. She didn't seem interested in my title at all, in fact, she was bored by it. "Oh, you're a prince? Yawn," she said. After reconnecting in South Africa, we began dating, but it wasn't always smooth sailing, especially while I was in the army. I remember one difficult conversation where we talked about our future and where we were heading. She knew I cared about her, but she felt unseen.

The duke and Davy ended their on-and-off relationship for good in 2010. In his book, Archewell cofounder revealed that Davy's apprehension about living a public life played a role in their breakup. He wrote, "Constant scrutiny is not something the entire world is equipped to handle, and I couldn't ask Chels to bear it. She wasn't sure if she was ready for that kind of life. Having someone constantly on your tail for the rest of your life? What could I say to her?" He also expressed his understanding of her desire for freedom.

In Harry's witness statement during his lawsuit against Mirror Group Newspapers, he referred to his past relationship with Davy more than a decade after their split. Harry stated that the media company's alleged unlawful actions had caused significant challenges in their relationship and ultimately led Davy to conclude that a royal lifestyle was not for her. Since their split, Davy has moved on and married Sam Cutmore-Scott, with whom she shares a son named Leo, born in 2022. In contrast, Harry has gone on to have two children with his wife Meghan, son Archie born in 2019 and daughter Lilibet born in 2021.

Keep scrolling for a look at Harry and Davy’s relationship timeline:

Credit: SplashNews.com

Prince Harry and Chelsy Davy’s Relationship Timeline: Split, Reunion at Prince William and Princess Kate's Wedding, More

They had a tumultuous relationship, with Davy struggling to cope with the intense media scrutiny that came with dating a member of the royal family. Despite their ups and downs, the two remained close friends and Davy even attended Harry's wedding to Markle.

"We were discussing the idea of hosting a dinner party one evening, but there was a catch - we didn't have any acquaintances in Cape Town," recounted the Duke of Sussex in his memoir, Spare, published in January 2023. "Or so we thought. However, I recalled meeting a girl named Chelsy from South Africa years ago at the Berkshire Polo Club. She struck me as unique and unbothered by superficialities, including my royal status." Harry affectionately portrayed the Zimbabwe-born Chelsy as someone who was "totally uninterested in putting on airs."

When I met her, she didn't seem like the type of girl who was determined to be a queen from the moment we met. She didn't have the typical "throne syndrome" that so many girls seem to have, according to the BetterUp CIO. I had always wanted to meet a woman who wouldn't be impressed by my title, but rather by my mind and heart. Chelsy seemed to fit that description perfectly - she was uninterested and even bored by my title. Our connection was based on something deeper. However, our relationship had its challenges, especially while I was in the army. We had difficult conversations about where our relationship was headed, and Chelsy felt like she wasn't being seen.

According to the Archewell cofounder's book, Spare, the duke and Davy ended their on-and-off relationship for good in 2010. The split was reportedly influenced by Davy's reluctance to live in the public eye and endure constant scrutiny. The duke understood and respected her desire for freedom, acknowledging that not everyone is cut out for a life of constant media attention.

In the prince's lawsuit against Mirror Group Newspapers, which took place more than a decade after their split, Harry referred to his relationship with Davy. In his witness statement, made public in June 2023, Harry claimed that the media company's alleged intrusions had caused significant difficulties in their relationship, leading Davy to determine that a royal lifestyle was not for her. Davy went on to marry Sam Cutmore-Scott in 2022, with whom she shares a son named Leo. Harry, on the other hand, has two children with Meghan: son Archie, born in 2019, and daughter Lilibet, born in 2021.

Keep scrolling for a look at Harry and Davy’s relationship timeline:

Credit: David Hartley/Shutterstock

2004

After meeting in South Africa, Harry and Davy started a romantic relationship. Harry was drawn to Davy's straightforward nature and carefree attitude. He admired how she dressed in miniskirts and high-heeled boots, danced freely, and enjoyed drinking tequila just like him. All of these qualities brought Harry joy and happiness.

Credit: Shutterstock

2007

Seated together at the Concert for Diana, a benefit event organized by Prince Harry and his brother, Prince William, the couple paid tribute to Princess Diana who passed away in a tragic car accident at the age of 36 in August 1997.

Credit: SplashNews.com

2008

Davy made her official debut at a royal function, attending Harry’s cousin Peter Phillips’ wedding to Autumn Kelly. 

Credit: Willi Schneider/Shutterstock; SplashNews.com

2010

The pair called it quits. Harry later attributed their breakup to Davy not wishing to live her life in the public eye. 

He expressed his understanding of her longing for liberation and stated that he would also prefer a life full of freedom if given the option. "Although I would miss her dearly, I comprehend that she values her freedom above all else," he penned in Spare.

Credit: David Hartley/Rupert Hartley/Shutterstock; Shutterstock

2011

Meeting again at William and Kate's April wedding, Harry wrote in his book "Spare" that he and Davy had not been in regular contact. Before inviting her, William checked with Harry to ensure neither of them would feel uncomfortable. Harry admitted it was difficult to reunite with Davy.

“There were still so many emotions lingering within me, emotions that I had buried deep down and emotions that I hadn't even realized existed," he revealed. "I couldn't help but feel a certain way towards the persistent, hungry-looking men who were constantly following her, circling around her and pressuring her to dance. That night, jealousy consumed me and I ended up confessing it to her, which only made me feel worse. I felt pathetic and powerless in that moment."

Credit: Shutterstock; FACUNDO ARRIZABALAGA/EPA-EFE/Shutterstock

2018

Davy's presence at Harry and Meghan's May wedding was a testament to their amicable relationship. The former lawyer looked stunning in a navy short-sleeved dress paired with a matching feathered hat.

Credit: WPA Pool/Shutterstock; Piers Allardyce/Shutterstock

2023

Harry's legal team argued in his lawsuit against Mirror Group Newspapers that his relationship with Davy could have endured longer if the press had not intruded. In his witness statement from June, Harry claimed that the company's unlawful actions created significant difficulties in his relationship with Chelsy Davy, ultimately leading her to decide that a life in the royal family was not for her.