Prince Harry and Chelsy Davy: The Duke’s ‘first serious relationship’ and its breakdown

They romanced overseas, they partied heavily, they remained on-again, off-again — until they weren’t.

They were Prince Harry and Chelsy Davy, a royal relationship that was anything but.

Truly embodying the spirit of the royal family entering a new era, the Duke of Sussex and his entrepreneur ex-girlfriend made a splash with their relationship for as long as it lasted.

The pair first met in England, circa 2004, but didn’t strike up a serious romance until they ran into each other again in Zimbabwe when the Duke of Sussex embarked on his gap year.

Following their reconnection, Harry and Chelsy went on to holiday in South Africa along with his then girlfriend’s family — a lucrative Zimbabwean business empire.

It is well known that the Duke’s South African tour helped him mend the cracks left in his life by his mother, Princess Diana’s death.

Fittingly perhaps then was Chelsy’s appearance at the memorial concert for the late Princess of Wales, in 2007.

All seemed to be going well despite the couple’s wild lifestyle — quite normal by modern standards, if perhaps, a little unconventional for royalty — as the Zimbabwe native businesswoman was even loved by her royal beau’s family.

Chelsy has been photographed mingling with Kate Middleton, who was still Prince William’s girlfriend at the time.

While even brushing shoulders with the future king himself and his father, King Charles, on occasions such as Harry’s Pilot Course Graduation at the Army Aviation Centre in 2010.

Coincidentally, 2010 was also the year when Harry and Chelsy went their separate ways — this time, for good.

Described by the Daily Mail as Prince Harry’s “first serious relationship”, what was the point of attraction and what went wrong with Chelsy Davy?

Keep reading to find out:

Glosse Posse

Per the Mail, “Chelsy and Harry were members of the so-called ‘Glosse Posse’” — an unofficial but extremely exclusive group, which was comprised of a lineup that included Tom and Tor Inskip, Harry’s childhood pals from Eton; the Harbord sisters, Astrid and Davina; among a few others.

To this group, Chelsy was described by Harry as the “best thing that ever happened to me”, as they continued to paint the town red.

However, these hard partying ways eventually caught up to the now mother-of-two, as she began worrying endlessly about her boyfriend’s whereabouts which did not get any less wilder when she wasn’t around.

The British tabloid further reported that “behind the scenes, Chelsy apparently had concerns about Harry’s roving eye and was often left in tears by the flurry of tabloid tales about what her boyfriend had been doing at his favourite nightclubs such as Boujis or Raffles.”

The breakup attempts

While Harry long believed that he had found his soulmate in Chelsy, the 39-year-old entrepreneur was often left overwhelmed at the wide reaching implications of being associated with her partner’s rather imposing household and whether that life was meant for her.

The Duke wrote in his memoir, “I loved Chels’s ease, that she wasn’t complicated.”

As for the reason he was so smitten with her? “She didn’t care what anyone thought. She wore miniskirts and high-heeled boots, danced however she wanted, drank tequila like me, and all of this made me really happy,” Harry added in Spare.

Honest to character, the miniskirt wearing and tequila guzzling socialite was not moved at the prospect of being bestowed with a royal title and initiated the pair’s first breakup in 2007 — just before Harry flew off on a six month military tour to Iraq.

However, once the couple had reconciled, Chelsy once again got cold feet and broke things off in 2009.

This time, the blow was harsher because it was done quite publicly.

Much like their modern romance, the relationship’s death knell was tolled by a simple click online, when Chelsy changed her relationship status on Facebook to say “Not in one”.

“Harry could not believe Chelsy had done it so publicly, and he was angry and upset when the story broke on the front page of The Mail On Sunday,” wrote royal correspondent Katie Nicholl in her book, The Making of a Royal Romance.

Though perhaps Harry would have appreciated her decision a bit more once the cloud of his anger must have evaporated, as Chelsy Davy had exercised her fiercely individual sense of independence that he cherished so much about her, to draw the curtains on a relationship which she felt had run its course.

Her friend’s recollection at the time of the split revealed, “She also wants to be her own person, not just Prince Harry’s girlfriend. She fully respects his career, but they just don’t get enough time together and she’s a bit fed up of always coming second.”

An amicable happiness

While Prince Harry and Chelsy Davy separated in 2010, the famous ex-girlfriend was back around her royal boyfriend the very next year, for his brother’s wedding.

An indication as any that Chelsy must have been greatly revered by the royal family, considering that even former British prime ministers were left off the guest list for Prince William’s wedding to Kate Middleton if Queen Elizabeth saw it fit!

Moreover, Chelsy also became one of the three ex-girlfriends of Harry’s to secure an invitation to his own wedding, where he tied the knot with Meghan Markle in 2018.

Chelsy Davy happily joined Cressida Bonas and the Duke’s rumoured ex flame, pop singer Ellie Goulding, as a guest at St George’s Chapel on May 19, seven years ago.