There was Harry and Chelsy before there was Harry and Meghan. Although Chelsy Davy started dating Prince Harry in 2004, they met long before when they attended school in England together. They got together through a mutual friend who thought the two might have chemistry, but nothing happened between them since Davy was planning to return to South Africa.
Despite this, Harry still fell head over heels for Chelsy, calling her the love of his life when speaking to a school friend. By the end of the summer, it’s safe to say that the two were smitten with each other, but fate had different plans in mind. But were they set up for failure from the start?
She was bored by the fact that he was a prince
According to Prince Harry, Davy was uninterested in Harry’s title, unlike other girls who were often afflicted with what he calls “throne syndrome.” While some royalty might be offended by this, Harry was surprised in a good way and was happy that she saw more to him than his title. Davy didn’t know much about the Royal Family, but in the end, rumors swirled that Chelsea was warned off by her parents, saying that dating a prince wasn’t worth “all the aggravation.”
Chelsy just wanted to be a normal girl
There’s no such thing as normal when you’re living the royal life, and the spotlight may have been too much for Chelsy Davy. She grew up barefoot in Africa, surrounded by nature, and in Cape Town, she had a traumatizing experience where she was held at gunpoint. Despite all these experiences, getting used to the paparazzi was the hardest part for young Chelsy, who felt uncomfortable with the never-ending attention. She worked long hours then, and when she wanted to go out and let off steam with friends, being scrutinized publicly made it nearly impossible. Tabloids would often paint her as a party girl when, in reality, she was so much more.
The tabloids interfered throughout their whole relationship
Prince Harry filed a lawsuit against Mirror Group Newspapers, claiming that tabloid harassment was the cause of their breakup. The prince believed that the tabloids always wanted him to be single and sold more newspapers when he was, so when he was in a happy relationship, they didn’t just report the nitty-gritty details: they did everything in their power to break them up and constantly follow the couple around, even on supposedly top-secret dates.
He didn’t want her to change
Davy was not concerned with royalty or appearances, which would have been quite a problem for the Firm. Therefore, her initial nonchalance, which charmed him, was turning into a problem. In the prince’s autobiography, he explains that while he adored that she dressed promiscuously, drank, and danced the night away, he was concerned about how his grandmother and the British public would feel about these antics.
Harry was scared the press would take away another loved ones
It’s no surprise that Prince Harry has a tenuous relationship with the paparazzi after what happened with his mother. The constant presence of the press throughout his relationship with Davy was relentless. Harry once discussed, in his 2023 witness statement, about picking Chelsea up from the airport and immediately seeing five separate photographers who were all there for him. He told Chelsy the experience was like a chronic illness that needed to be managed, but she wasn’t so sure. Ultimately, dealing with the paps is a big part of being with Harry, and she couldn’t handle it.
King Charles III disapproved of them dating
Royal expert Katie Nicholls wrote in her book that when Chelsy Davy was introduced to Harry’s father, King Charles did not support their relationship, although he claimed to like her. Based on reports, his dad thought it was an instance of “puppy love.” According to a tabloid piece. While we’ll never know how much of that is true, Harry has admitted that there was a disagreement between him and his father.
Their relationship was a rollercoaster when he was in the army
When Prince Harry served in the military, it was a tumultuous time for him and Chelsy. Although Harry expressed a desire to be stationed in Iraq, Chelsea wanted the opposite and worried about him being there. It led to many discussions, but he ultimately decided to serve, even though Chelsea asked him not to be a hero. She was also not impressed that he attended strip clubs with his army buddies; we can’t blame her for that one.
Harry didn’t know if Chelsea was the one
We all go through relationships, and not everyone you date becomes your person. Prince Harry wasn’t positive that the carefree Davy was “the one” and, in his autobiography, recounted a conversation with a friend that it took a specific kind of person to handle the scrutiny of his life. When she was in Cape Town, she explained to him that the paparazzi were constantly following her, and she hated it, asking him to do something about it. All he could do was tell her he was sorry, but he understood, saying that he wouldn’t want that sort of life if he had a choice.
They were delusional about their love
Although they broke up once, they were back together by 2010, but that spark wasn’t rekindled for very long, as the same old problems kept bubbling up. Harry’s confidante, Teej, helped him gain clarity and explained that they were “postponing the inevitable.” His friend urged Harry to allow the next breakup to be final and not waste any more time. In his memoir, the prince admitted that he and Chelsea were “willfully delusional” about making things work.
They were convinced by Prince William and Princess Catherine’s wedding
Despite being broken up, Chelsy Davy still attended Prince William’s wedding to Princess Catherine. After seeing how grandiose and over-the-top the day was, it was the nail in the coffin for Chelsea, who was convinced that separating from Harry was the right idea. Privacy was a major value for her, and she would never get it in the lifestyle of a royal bride. In the end, Harry ended up with Meghan Markle, and Davy married a schoolmate of Harry’s from Eton College named Sam Cutmore-Scott.
