Laughing together at a rugby match. Whispering sweet nothings at the polo. Smooching in the stands at the 2007 Cricket World Cup.
She was the leggy blonde in aviators and a miniskirt, known for her throaty laugh and playful sense of adventure.
He was the hunky prince with ruddy cheeks and a rebellious streak, the royal poster boy every 20-year-old wanted to date.
They were two young things in love; indeed, such was the promise of his relationship with Chelsy Davy that Prince Harry, then just 24, is said to have told his father: ‘Papa, she’s the one.’
As it turned out, she was not the one for him – and in 2009, after five somewhat turbulent years together, Chelsy ended things with her royal beau, announcing their break-up with a series of broken heart emojis on Facebook, where she wrote: ‘Relationship: Not in one.’
Though there were rumours of a reconciliation around the time of his brother William’s marriage to Catherine in 2011, both denied them. Harry professed he was ‘100 per cent single’, while Chelsy, the Zimbabwean-born daughter of a farmer and a former model, cited the incompatibility of their life choices.
Speaking in 2023, as part of a submission to the High Court, the prince would later blame press intrusion for their separation, claiming his first love had decided ‘a royal life was not for her’. One might assume such a momentous break-up, at such a tender age, would mar young Chelsy’s life for good. Losing a prince, and parting ways with the gilded life he had promised her, must – surely – be a source of lifelong regret?
But this could not be further from the truth.
Chelsy and trainee helicopter pilot Harry in 2010
Indeed, friends reveal Chelsy has positively thrived in the years since she split from Harry, with one telling the Daily Mail: ‘She’s never been happier.
‘It’s strange to think of the parallel life she would be living if she’d stayed with Harry. But that was a long, long time ago.
‘That break-up was probably the best thing that ever happened to her.’
Pictures released this week, and an accompanying rare interview, give a glimpse of the paradisical life she is now leading – on the Indian Ocean archipelago of Mauritius.
The previously unseen photographs – taken at her wedding to hotelier Sam Cutmore-Scott, 40, an old Etonian who was in the year above Harry, in 2022 – show Chelsy glowing and relaxed as the couple exchange vows on the beach.
In another picture she cradles their one-year-old daughter, Chloe, in one arm while holding hands with son Leo, now three.
The whole family is barefoot, natural and carefree, backlit by the golden Mauritian sunshine, white sand and glittering turquoise water.
Far from being haunted by the end of the relationship that thrust her into the spotlight, Chelsy seems to have flourished out of it – and her life is going from strength to strength.
The former couple in the Royal Box at the Cartier International Polo Match in 2006
Her jewellery brand, Aya Jewels, which she launched in 2016, having walked away from a career as a London solicitor, is thriving.
With its covetable range of diamond rings from £150 and gold necklaces from £495, documents lodged at Companies House last year show Aya had over £175,000 in the bank, a figure which has risen year on year.
Now a successful businesswoman running her own company, Chelsy is reaping the rewards of being her own boss – and no longer being tied to one place.
With neither of her children yet at school, friends say she regularly flits between London and Mauritius, where she works remotely and catches up with her parents, Charles, a successful Zimbabwean businessman, and Beverley, a former beauty queen and Miss Rhodesia, who now live on the island.
A glimpse at her Instagram account, where her 68,000 followers are regularly treated to smiling selfies and jaw-dropping sunset scenes, shows she is something of a jet-setter, visiting Turkey, Greece, France, Italy, the Czech Republic and America in recent years.
But it is Mauritius that has her heart – so much so that she is planning on moving her young family there full-time.
‘We got locked down on the island while visiting my parents during Covid,’ she explained this week.
‘While we were here, we got a bit further under the skin of the place from a non-holidaying perspective.
Chelsy is now married to Sam Cutmore-Scott, an old Etonian who was in the year above Harry at school
‘It’s a bright, colourful, friendly dynamic and people just smile. All. The. Time. Most importantly to me, there’s a wonderful sense of community. Neighbours pop in for a sunset drink while the big kids teach the little kids how to catch crabs on the beach.’
Community is important to Chelsy – and she has surrounded herself with a tight-knit group of friends, relatives (her cousins also live on Mauritius) and colleagues who closely guard her private life and that of her family.
Memories of those days fleeing the paparazzi and hiding out in ‘Club H’, Prince Harry’s secret party rooms in the basement of Highgrove House, after all, still run deep.
Chelsy has described feeling ‘hunted’ and ‘terrified’ during that time. Though now 20 long years ago, it is something she has no desire to repeat.
Though never a diva, Chelsy commands unwavering loyalty from her circle of girlfriends, many of whom she has known since her days dating Harry. Chief among her confidantes is Lady Melissa Percy, whom she calls ‘Missy’, an ex-girlfriend of Thomas van Straubenzee, a close pal of Harry’s.
Among friends, even at 40, she is known as the wild one, and has a reputation for being free-spirited and spontaneous.
This, says Ingrid Seward, royal biographer and editor-in-chief of Majesty magazine, was the trait that first drew Harry to her.
‘She was the love of his life; that first love you never forget,’ Ingrid adds. ‘Their relationship was very passionate and romantic, with lots of dramas behind the scenes.
Chelsea and husband Sam have two children, Chloe and Leo
‘She got on very well with Wills, who used to tease her about her South African accent, and with Catherine when she was younger.
‘In those days, Harry was something of a free spirit, and Chelsy touched that chord within him.
‘They bonded over his passion for Africa and they used to go on these wonderful trips abroad together.
‘They just gelled – he was utterly head over heels for that girl.’
As well as bringing out his fun side, Chelsy can be credited with encouraging her sometimes-wayward boyfriend to toe the line for his family.
When staying the night at Highgrove, she was happy to abide by Charles’ rule that the pair must sleep in separate rooms under his roof. And sources say it was she who urged Harry to take out a line referring to Kate’s ‘killer legs’ in his best man’s speech at his brother’s 2011 wedding.
But the characteristic that drew them together was, ultimately, what would tear Chelsy and Harry apart.
‘She knew, as Cressida [Bonas, whom Harry dated from 2012 to 2014] did, that royal life just wasn’t for her,’ says Ingrid.
‘She was intelligent enough to see that from an early age.
‘She wasn’t over-powered by ambition to better herself, or to marry into the Royal Family.
‘At the end, she said to him: “There’s no way this is ever going to be my future.”
‘And she was right. She would have hated it all, especially the Montecito madness that is now Harry’s life.’
Certainly, when one compares Chelsy’s life today with that of Harry and Meghan, their two worlds could not be more different.
With the latter ensconced in a £22.6 million mansion in a wealthy Californian neighbourhood, Chelsy and Sam are on the verge of emigrating from Chiswick, West London, to a tropical paradise in the Indian Ocean, far from the trappings of celebrity.
Grand Baie, where they spend most of their time, is an unspoilt enclave populated by fishermen, families and artisans.
Even their wedding, at the Paradis Beachcomber Resort, where rooms start at £400 a night, is believed to have been a low-key affair: Chelsy bought her dress, a cream-and-gold embroidered gown, from a hotel boutique the day before the ceremony.
Windsor Castle, with liveried footmen and a horse-drawn carriage, this was definitely not.
It helps, of course, that Chelsy’s husband is a down-to-earth chap – a ‘kindred soul’, says Ingrid Seward – whose ethos in life very much matches hers.
Oxford-educated Sam spends much of his time in north Norfolk, where he opened a boutique hotel, The Harper, four years ago, and recently revamped two pubs.
His family is in the hospitality business: his parents set up the Bijou Collection, a group of exclusive wedding venues across the UK and France, of which he is now managing director. His brother, Jack, is an actor.
He described his love for the Norfolk coast in a recent interview, saying: ‘There’s no better place to blow some cobwebs away…Huge skies, boats, birds. Nothing more required.’
Sam prefers to keep his personal life offline – and doesn’t use social media. Chelsy more than makes up for it, with a slew of regular, upbeat posts about her family life and burgeoning business.
Everything she shares is genuine, honest and unfiltered – and, unlike Meghan, she hasn’t felt the need to drop her surname.
‘Because of her relationship with Harry, Chelsy’s name will always be known,’ says Ingrid.
‘That’s something she can’t escape – but hopefully these days she can use it to her advantage, rather than feeling trapped by it.’
When they finally separated for good in 2011 Chelsy and Harry vowed they would ‘always be good friends’ and they appear to have stuck to it – for a while, at least.
She attended his 2018 wedding to Meghan, single and smiling, and didn’t seem to mind being snubbed from the more intimate evening reception at Frogmore House.
A friend told Vanity Fair Chelsy had ‘been trying [and failing] to get in touch with Harry’ in the days before his wedding, but he was ‘proving very difficult to reach’.
Since then, however, the pair appear to have drifted apart. Though it’s not clear what contact they have behind the scenes, it cannot be easy to maintain a friendship between Montecito and Mauritius, 11,500 miles apart.
Perhaps tellingly, Chelsy and Meghan don’t follow one another on social media; nor does Chelsy follow the Duchess of Sussex’s saccharine lifestyle brand, As Ever.
This may be unintentional, of course. Or it may be because, two decades on, Chelsy realises what she has known, deep down, all along: that saying no to a lifetime with Harry was the best thing she ever did.
