She’s often described as ‘the one that got away’.
Before settling down with Meghan, Prince Harry had an on-off relationship with Chelsy Davy, the daughter of a wealthy Zimbabwean businessman.
They got together in 2004 during Harry’s gap year travels in Zimbabwe, where Chelsy’s millionaire father owns and runs a game reserve.
What followed was Harry’s first serious relationship, which saw him travel on holiday to South Africa with her family. And Chelsy was by his side for the Diana memorial concert in 2007.
But their romance was turbulent, and while it spanned seven years, it ultimately ended for the final time in 2010, 15 years ago.
In his memoir Spare, Harry wrote: ‘I loved Chels’s ease, that she wasn’t complicated.
‘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.’
But 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.
Before settling down with Meghan, Prince Harry had an on-off relationship with Chelsy Davy, the daughter of wealthy Zimbabwean businessman (Pictured in 2006 in the Royal Box at the Cartier International Polo Match)
Their turbulent romance ultimately ended for the final time in 2010 (Pictured in 2008 at a service of remembrance and thanksgiving at the Holy Trinity Church in Windsor)
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 (Pictured at the Guards Polo Club in 2006)
Vanity Fair’s royal correspondent Katie Nicholl wrote about their seven-year flame in The Making of a Royal Romance.
Chelsy and Harry were members of the so-called ‘Glosse Posse’ – an exclusive group of friends including some of their best pals from Gloucestershire, siblings Tom and Tor Inskip; the Harbord sisters, Astrid and Davina; Guy Pelly; Julian Isaacs, Viscount Erleigh; and Natasha Rufus Isaacs.
Harry would even tell his friends Chelsy was the ‘best thing that ever happened to me’ – showing that, had things been different, they could easily have stood the test of time together.
But in 2009, when Harry was training in the Air Force, Chelsy broke things off very publicly with the Prince.
Nicholl wrote: ‘While Kate had been prepared to wait for William as he embarked on his flying career, Chelsy was not.
‘She was lonely and desperately homesick. She told Harry she felt the relationship had run its course and removed from her finger the blue topaz ring he had given her as a birthday present.
‘Then she did something which infuriated him: she changed the status on her Facebook page to “Relationship: Not in one”.
‘The relationship was over in the click of a button. 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.’
Vanity Fair’s royal correspondent Katie Nicholl wrote about Chelsy and Harry’s seven-year flame in The Making of a Royal Romance
In his memoir Spare, Harry wrote: ‘I loved Chels’s ease, that she wasn’t complicated’ (Pictured as the then Prince of Wales, Charles III, presents flying badges to students, including Prince Harry)
A royal author wrote: ‘While Kate had been prepared to wait for William as he embarked on his flying career, Chelsy was not.’ Chelsy and Kate are pictured in July 2006
It wasn’t the first time Chelsy had called quits on the relationship. She reportedly called things off with Harry before he left for a six month tour of Iraq in 2007, just a week after he was photographed falling out of a London club with ‘favourite drinking buddy’ Natalie Pinkham.
But this time, things were different.
One of her friends reportedly said, according to Nicholl, ‘Chelsy was fed up of just being Harry’s girlfriend.
‘She felt she was making all the effort and he wasn’t making enough.
‘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.’
Chelsy reportedly struggled with the relentless attention, ultimately leading her to decide that a royal life was not for her.
Chelsy and Harry have stayed amicable since breaking up and in 2011 they went to Prince William’s wedding together.
Harry got back in touch with Chelsy to invite her to his wedding to Meghan in 2018. He also invited his other old flame Cressida Bonas – but the invites were for the ceremony only.
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Harry and Chelsy laugh together during the Investec Challenge international rugby match South Africa vs. England in Twickenham in 2008
Chelsy and Harry at the Army Aviation Centre, Middle Wallop, Hampshire on May 7, 2010
The then Prince Charles, Chelsy and Harryat the medal ceremony at the Hampshire Army Aviation Centre
An emotional phone call followed, with the conversation reportedly acting as closure for the former couple.
But body language expert Judi James said that Chelsy’s feelings were evident during the wedding.
She told the Daily Mail: ‘When she arrived, everyone else was chatting and laughing, but she sat in the pews just looking to one side – gazing reflectively into space and biting her lips slightly.
‘She was doing that at the end as well. It was almost the soap opera part of the ceremony.’
In his memoir Harry reflected his ex-girlfriend was ‘unlike so many girls he met’ because she didn’t have ‘throne syndrome’ and ‘wasn’t visibly fitting herself for a crown the moment she shook his hand‘.
Chelsy and Harry are pictured at the Concert for Diana in June 2007
Chelsy is pictured arriving at Harry and Meghan Markle’s wedding in May 2018
In the 15 years since the couple broke things off, Chelsy has had two children, a boy and a girl, and married her boyfriend of three years, Sam Cutmore-Scott, in a secret ceremony in 2022.
Cutmore-Scott was in the year above Harry at Eton College and is managing director at The Harper Hotel in Holt, the family business.
The couple are believed to split their time between a townhouse in Chiswick and the Norfolk coast.
Chelsy seems to be enjoying her life outside of the public eye, not sharing the news of the birth of her son until three months later when he was introduced to their local parish council in Norfolk.
Many of her friends didn’t even know she was pregnant.
Earlier this year expert Richard Fitzwilliams told Femail: ‘In his controversial memoir, Harry eulogises Chelsy as being a free spirit who didn’t care about his royal connections.
‘The pressure of dating a royal finally took their toll on the relationship.
‘She had the free spirit and independence Harry felt he needed.
In his bombshell memoir Spare, Harry reflected that his ex-girlfriend was ‘unlike so many girls he met’ because she didn’t have ‘throne syndrome’
‘She has also never given interviews about their relationship.
‘Everything we know about her is that she is a truly loyal and lively person whose attitudes are light years away from the destructive and calculated ruthlessness which Meghan has so clearly shown.’
In an interview with Tatler in 2020, Chelsy reflected: ‘I’m very happy with where I am right now. I’m happy with everything.
‘I’m doing something in Africa that I’m passionate about and I’m excited for what my vision is and what that will create. Everything is falling into place.’
It seems that Chelsy has achieved the quiet life that Harry has expressed he so desires.
PRINCE HARRY’S RELATIONSHIP HISTORY
Before the royal tied the knot with Meghan, he dated a number of women, including some well-known faces.
Ellie Goulding
Among them was UK-based singer Ellie Goulding, who Harry is reported to have dated before meeting Meghan Markle in the summer of 2016.
Described as a ‘fling’, the couple’s most notable outing was at the Audi Polo challenge in Coworth Park, Berkshire, with onlookers saying that the couple were ‘all over each other.’
It is thought that Harry had been friends with Ellie since they met at Prince William’s wedding in 2011.
Jenna Coleman
Another famous woman Prince Harry is rumoured to have enjoyed a fling with is Doctor Who star Jenna Coleman, with whom he was alleged to have enjoyed a ‘flirty’ night with in a ‘tactile’ after-dark encounter during an A-list polo party.
Witnesses said the royal took the then 29-year-old actress by the hand for a private chat after the Audi Polo Challenge at Coworth Park in Ascot.
One onlooker told The Sun: ‘It looked like they were really enjoying each other’s company.’
Cressida Bonas
This was two years after Harry’s relationship with actress and society girl Cressida Bonas.
Cressida and Harry were together between 2012 and 2014, and many people thought that they would end up getting married.
Mollie King
Before his relationship with Cressida, it was rumoured that the Prince had a fling with singer Mollie King in 2012.
The pair met at a polo match in 2010 and were pictured partying together at Public nightclub and Bunga Bunga karaoke bar in London.
They were allegedly set up by Harry’s cousin Zara Phillips, who is a friend of the pop star’s Saturdays bandmate, Una Healy.
It was reported Harry broke things off with the singer after a few months because she was too open about their relationship.
Florence Brudenell-Bruce
The Duke of Sussex has also been linked to Florence Brudenell-Bruce, with the pair reportedly dating in 2010.
According to friends, the lingerie model and society star – who is now married to business man Henry Edward Hugh St George – found the attention that came with dating a royal hard to deal with.
‘Flee hated all the press attention she got when she was dating Harry,’ a source was quoted as saying at the time.
‘She really liked him but she was embarrassed by being splashed all over the papers.’
Caroline Flack
And before Florence, there was TV presenter Caroline Flack in 2009, who called herself ‘Prince Harry’s bit of rough’, before she went on to date singer Harry Styles.
Chelsy Davy
Despite Harry’s bad boy reputation and ‘flings’ he had one very serious girlfriend between around 2004 and 2011.
Businesswoman Chelsy Davy was expected to become Prince Harry’s wife by many, until they eventually split.
Natalie Pinkham
According to reports, during 2006, the prince was rumoured to be dating Natalie Pinkham after pictures surfaced of the pair.
A source reported at the time that Harry was ‘absolutely infatuated’ with the TV presenter.
Astrid Harbord
Another relationship he is rumoured to have enjoyed was with the Princess of Wales’ good friend Astrid Harbord back in 2009.
Astrid is now a company director, and founder of Lady Garden, a national women’s health charity encouraging conversation about gynaecological health.
