Before Meghan Markle, Prince Harry‘s heart belonged to Chelsy Davy, the carefree daughter of a controversial millionaire Zimbabwean safari operator. Their turbulent love story lasted five years. New reports say her company and a trip to Botswana were the only things that could calm 23-year-old Harry down after a disappointing deployment in Afghanistan with the British Army in 2008.
Harry’s time in Afghanistan
Prince Harry nearly quit the army after he was kept from serving in Iraq at the last minute in 2007, per a 2008 report by The Guardian. Extensive media coverage of his deployment and a consequential rise in threats on the ground led the head of the British Army to reconsider his trip, which left the prince feeling “very disappointed,” and “more than a bit depressed,” a close source told The Standard at the time.
That all changed when his grandmother told him he’d be going to Afghanistan. His excitement was clear in an interview given to the British press pre-departure that was kept unpublished until his dreams were crushed again two months later.
A bit of excitement, a bit of: ‘Phew, finally get the chance to actually do the soldiering I wanted to do from ever since I joined'”
The lead-up to his Afghanistan mission contextualizes Prince Harry’s frustration when his location was leaked by international media, more specifically the U.S.-based Drudge Report website. The U.K. tabloids had agreed to an embargo and surprisingly respected it all the way through, but in February 2008, just two months into his planned four-month tour, Harry’s whereabouts in the southern Helmand province and his role as a forward air controller became public and his deployment was called off once again.
The royal was in charge of “coordinating air support and aviation across the area,” and guiding fighter jets towards “suspected Taliban targets,” per The Guardian. He would return to the Middle Eastern country in 2012, later confessing to killing 25 people during his two tours, who he described as “chess pieces”.
According to a royal expert for The Mirror, Harry was “furious” and it took an off-the-grid trip to Botswana with girlfriend Chelsy Davy to bring him back down. “Where did he go? Straight to Botswana with Chelsy Davy. Straight there and spent a couple of weeks there. Almost like — it’s where he goes when there’s steam coming out of his ears to calm down,” explained Duncan Larcombe.
Chelsy Davy was “different”
There’s a reason why Chelsey Davy was Harry’s longest relationship before Meghan Markle. In his 2023 memoir Spare, the Duke of Sussex explained that “unlike so many people [he] knew, [Davy] seemed wholly unconcerned with appearances, with propriety, with royalty.” He loved that she “wore short skirts and high boots, danced with abandon, [and] drank as much tequila as [he] did.”
The two met at a polo match in the U.K. and began dating shortly after when Harry traveled to Cape Town, South Africa, where Zimbabwe-born Davy was studying and the prince invited her over for dinner. Although they only officially broke their romance off in 2010, there were rumors of temporary splits as the law student struggled with the long-distance relationship, Harry’s rowdy partygoer lifestyle, and public scrutiny.
When the prince filed a lawsuit against News Group Newspapers (The Sun, News of The World) for invasion of privacy in 2020, court documents revealed that Davy suspected she had been bugged and wiretapped by tabloids. “‘It takes a certain kind of person to withstand the scrutiny, (…) and I don’t know if Chels can handle it. I don’t know that I want to ask her to handle it,'” Harry recounted in his memoir.
The two remained close friends, with Davy attending both William and Harry’s wedding ceremonies. She married hospitality industrialist Sam Cutmore-Scott in 2022 and works in the Fine Jewellery and Luxury Travel industries as the founder of the brand Aya.
The couple’s restorative trip to Botswana
The two lovebirds’ escapade in the African country, where they spent most of their time in a traditional houseboat called the Kubu Queen on the pristine Okavango Delta, was reported extensively back in 2008. Hello Canada said the two slept “in a tent for two perched on the roof of their boat,” and would cook breakfast on a small gas stove on the main deck every morning.
Harry and Chelsy spent their days sunbathing, riding speedboats, and admiring nature, which included crocodiles, otters, and hippos. Nearly 10 years later, in 2017, Harry took Meghan to the same country, a favorite destination for the prince, to celebrate their first year together and his then-girlfriend’s 36th birthday. They opted for a bit of in-land “glamping” on that occasion.
