Prince Harry met Chelsy Davy back in 2004, when he was on break from Eton. Chelsy was a student at both Stowe School and Cheltenham Ladies College, and students at each school definitely spend time together. The two reportedly fell for one another quickly.
Chelsy didn't make her official debut as Harry's girlfriend until 2008, but it was clear in the intervening the years that the couple were definitely together. Chelsy was often photographed alongside Kate Middleton (who was navigating her own ups and downs with Prince William) and attending the 2006 Concert for Diana as Harry's date.
The pair were hounded by the media from essentially day one, which isn't that surprising considering how Meghan Markle and Prince Harry have been treated in recent years. Chelsy eventually opened up about what the experience was like.
Harry and Chelsy's relationship had its ups and downs.
While Harry and Chelsy dated for seven years, it seems the relationship wasn't strictly exclusive the entire time. They reportedly broke up for a bit in 2006, and Harry was rumored to have revived things with former flame Natalie Pinkham. However, they patched things back up, and Harry released a statement about Chelsy ahead of his 21st birthday.
Harry admitted he couldn't talk about Chelsy publicly.
One challenging aspect of their relationship was that Harry and Chelsy simply couldn't behave like a regular couple. He once spoke on the topic, noting, "My girlfriend is somebody who is very special to me and yes, she's gone through some very hard times. I would love to tell everybody how amazing she is. But you know this is my private life and once I start talking about that, then I've left my own self open. I get to see how upset she gets and I know the real her. Unfortunately, I can’t turn to people and say, 'Listen, she's not like that, she's like this.' But it's part of the baggage that comes with me, and she understands that and my friends understand that as well."
The two sparked engagement rumors in 2007.
By 2007, the press was reporting that the pair were engaged, but both Harry and Chelsy were quiet on the topic. Later that year, they allegedly broke up, but the reasons weren't perfectly clear. While some blamed Harry's lack of commitment to the relationship, Chelsy recently shed light on other aspects of their time together that might have contributed.
Near-constant media attention made things hard.
Chelsy recently explained that the intense media scrutiny was challenging: "I found it very difficult. I couldn't cope. I was young, I was trying to be a normal kid and it was horrible."
Chelsy also says the paparazzi were difficult to deal with.
Chelsy added that having photographs taken at all hours of the day and night didn't help: "I like to enjoy life, but I like to achieve things and am very ambitious. They can be forgiven for not knowing I was working really hard, I didn't shout about it. If you go out once, they take a picture, but they don’t take a picture of you going to work every morning, it's [photos] of you falling out of a nightclub at 4am."
Prince William's wedding might have had something to do with it.
Interestingly, attending Prince William and Kate Middleton's wedding in 2011 might have been what sealed the deal for Chelsy. As royals author Katie Nicholl explained her book Duke of Sussex, Harry: Life, Loss and Love, "The life of a royal bride was not for her and she told Harry she could never make the sacrifices Kate had made."
The pair broke up in 2009.
In light of their time together, it's not a huge surprise that the pair broke up in 2009. At the time, a royal source explained what happened to People in general terms: "They are remaining friends. There have been all sorts of reasons given [for the split] but suffice it to say they felt that it had run its course."
But they reunited in 2010!
It seems the breakup might have been too much for the couple to bear. They ended up back together in 2010, but broke up after a month. Harry reconnected with Chelsy ahead of Prince William's wedding the following year, but the reunion didn't end up lasting.
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