Chelsy Davy: from party princess-in-waiting to millennial mother 1/32Prince Harry and Chelsy Davy - In pictures

During the mid-noughties, it would have been a small miracle if you opened a newspaper on any given day and didn’t see a photo of Kate Middleton or Chelsy Davy.

As the longterm girlfriends of Prince William and Prince Harry, there were new snaps of them at the polo, attending society weddings, tumbling out of Chelsea clubs every day.

We of course know what became of the now Duchess of Cambridge: a 2011 live-streamed wedding, ascent to royal stardom and three children (an heir and two spares). But what of Harry’s former flame, Chelsy Davy?

The glamorous Zimbabwean was Harry’s most famous and long-term girlfriend, appearing on his arm and splashed across tabloid pages for the best part of a decade. But in January this year, the 36-year-old gave birth to her first child, a baby boy called Leo, with hardly anyone outside her circle even knowing she was pregnant – or, indeed, who the father was.

On some level, it’s not altogether surprising. Though Chelsy was one of the world’s most recognisable faces during the seven-year period from 2004-2011, where she dated Harry on and off, she found the scrutiny of the British press difficult to handle. Since the couple parted ways over a decade ago she has resolutely tried to stay under the radar, giving only a couple of interviews and shedding many of the friends she had during her days with Harry.

Most of the people I speak to who used to run in the same circles as her haven’t seen her in years – “I really don’t know who her scene is now at all,” admits one west Londoner who used to be in her crowd – and another source who’s been friends with Chelsy for over a decade says: “She has fiercely guarded her private life since this new boyfriend.”

Harry and Chelsy were just teenagers when they met. Chelsy grew up in Victoria Falls — the daughter of a wealthy businessman and an ex-model — on a game park twice the size of Surrey managed by her father. There she roamed free, running around barefoot with herds of buffalo and battling with monkeys as they tried to steal the balls on the tennis courts.

But when Robert Mugabe came into power and implemented his land reform programme, her father was forced to give up all his arable land and their family home was destroyed. At the age of 14, an academically ambitious Chelsy realised her educational prospects at home were limited and begged her parents to let her leave and go to boarding school in England. They relented and settled on Cheltenham Ladies’ College, followed by Stowe for sixth form. It was here that she first met Harry.

To start with the pair were just friends, and by the time Chelsy finished her A levels she missed Africa so much that she left for the University of Cape Town to carry on her education, taking a degree in PPE. When Harry arrived in the city on his gap year, he decided to look her up – little did either of them know that it would mark the beginning of the longest relationship of his life to date.

After Cape Town, Chelsy decided to return to Britain to undertake a two-year law degree at Leeds University – and, almost certainly, to be closer to Harry.

They were a golden couple, with Chelsy hailed as the cool, sexy girlfriend, so different from the sort of prim English girl who Harry might have chosen. Here was someone who wasn’t afraid to have fun – even perhaps a little too much fun, if the paparazzi shots of her falling out of nightclubs was anything to go by – and you’d often see her cheering him on from the side lines during polo matches, wearing a mini skirt and a mischievous grin.

Known for her infectious laugh – a throaty ex-smoker’s growl – she was a refreshing antidote to the more demure Kate Middleton.

Chelsy Davy: from party princess-in-waiting to millennial mother 1/32Prince Harry and Chelsy Davy - In pictures

During their relationship Chelsy was part of a set known as the ‘Glosse Posse’ (so named for its ties to Gloucestershire), an exclusive gang of friends that included Prince Harry, Guy Pelly, Natasha Rufus Isaacs and Tom ‘Skippy’ Inskip, one of Harry’s closest childhood friends. They all congregated at ‘Club H’, Harry and Prince William’s basement den at Highgrove. The young couple went on holiday to South Africa with her family, she was invited to Prince Charles’ 60th birthday and it was Chelsy who was by Harry’s side at the Diana memorial concert in London in 2007.

But while they were very much in love – in the 2011 documentary ‘William and Kate into the Future’, royal author Richard Kay noted that Chelsy was Harry’s “real love match” and that there was “great passion between the two of them” – cracks were beginning to show. As a solicitor for the ‘magic circle’ City law firm Allen & Overy, Chelsy worked hard and occasionally partied harder, but unsurprisingly it was only the stories about her drunken nocturnal antics that ended up in the papers. “Chelsy’s Five-hour Bender” screamed one News of the World headline in 2005; “Chelsy Shows She Can Out-Party Prince Harry” proclaimed another two years later. Even once they’d split up, the paparazzi still followed her wherever she went. “Partying Till 7am, Flirting With Handsome Men... Looks Like Chelsy Isn’t Exactly Missing Her Prince” read one Daily Mail headline just after their breakup.

The press were relentless in their pursuit of her; in the BBC’s two-part series ‘The Princes and the Press’ last year, one private investigator, Gavin Burrows, revealed the lengths he went to to dig up dirt on Chelsy, saying she became an “object of obsession” for investigators, claiming that phone hacking was used to obtain information about her. “There was a lot of voicemail hacking going on, there was a lot of surveillance work on her phones, on her comms,” he said. “Chelsy would brag to her friends when she was going to see him.” He said investigators were particularly interested in her medical records – “had she had an abortion, sexual diseases?” – as well as information about her ex-boyfriends and details of her education, though Burrows’ claims are yet to be tested in court and are strongly disputed.

A deeply private person, Chelsy struggled with the level of scrutiny. In an interview with The Times in 2016, she revealed, “It was so full-on: crazy and scary and uncomfortable. I found it very difficult when it was bad. I couldn’t cope. I was young, I was trying to be a normal kid and it was horrible.” Harry even spoke out about the subject when he gave an interview to mark his 21st birthday. “I can see how upset she gets,” he said. “My girlfriend is somebody who’s very special to me, and yes, she’s gone through some very hard times.”

It is said the final straw came when William and Kate got engaged and Chelsy saw the media frenzy that surrounded the royal wedding. In royal author Robert Lacey’s 2020 book, Battle of Brothers, he wrote: “According to a friend, she told Harry that she could never make the sacrifices she had witnessed Kate making, particularly when it came to moulding her life around the unremitting attention of the press.”

After their breakup, Chelsy sought refuge back in Zimbabwe before returning to London and living a relatively low-key life in a series of bachelorette pads in Chelsea and South Kensington. She left her high-powered City job and started her own business in 2016, an African jewellery brand called Aya, which more recently she’s grown to incorporate lifestyle and travel elements.

She attended Harry and Meghan’s wedding in 2018 and has said she “will always be good friends” with the prince, but no longer runs in the same circles she used to. Instead, she has cultivated a core group of incredibly close friends – among them Lady Melissa Percy, whom she met through Harry, and Irene Forte, the daughter of hotelier Rocco Forte – who would have been the first to know about her relationship with the father of her child, handsome Old Etonian Sam Cutmore-Scott.

Since Harry, Chelsy has managed to keep her subsequent romantic relationships quiet – until recently, her last known boyfriend was the television producer James Marshall, whom she split up with in 2018. In an interview with Tatler in 2020, Chelsy revealed there was a special person in her life, but refused to share his name. “Yes, there is someone, and I am quite taken by this one, but it’s very new and I don’t want to say too much.”

It’s almost certain that boyfriend was Sam, whom she was photographed out and about with in Soho in 2019. Now it’s reported that she’s left her South Kensington flat to live in Sam’s four-storey Victorian terrace in Chiswick (her removal from her usual paparazzi-filled stomping ground of SW3 is thought to be the reason no one knew about her pregnancy). And if recent photographs of her wearing an enormous sapphire ring are to be believed, the duo are set to tie the knot.

So who is Sam Cutmore-Scott? While he may have been in the year above Harry at Eton, the 37-year-old has never been a key player on the social scene – in fact, no one I spoke to in Chelsy’s old set even knew who he was, and all the Old Etonians I asked were more familiar with his dashing younger brother Jack, an actor who starred in Christopher Nolan’s Oscar-winning film Tenet and the US drama series Deception.

A successful hotelier, Oxford graduate Sam is a director of his parents’ hospitality company, the Bijou Collection, which owns four exclusive wedding venues, including an abbey in Buckinghamshire and a chateau in the South of France, and last year he opened an upmarket Norfolk hotel, The Harper, which he owns along with his family.

Norfolk has clearly become something of a refuge for Chelsy, too. “She’s been spending a lot of time there,” says one friend. Chelsy’s already put her own stamp on the hotel, where the spa is stocked with products from close pal Irene Forte’s beauty line, and a glance at her Instagram page reveals a picture of her cockapoo, Biscuit, sitting in a rolltop bathtub at the property. She’s also shared images of walking her dogs on the beach a few miles away.

It is unclear what Chelsy’s next move will be now that she has Leo, who she gave birth to at Chelsea and Westminster Hospital in January. “I think she will keep going with the travel side of her business in particular,” says a pal. “I feel for her, as she is not comfortable in the public eye and now there is all of this interest in her again.”

There is one thing that everyone I speak to agrees on, though. “She will be an incredible mother.”