He’s regarded as one of the world’s most eligible bachelors and as Prince Harry is taken off the market, there’s little doubt he’s broken the hearts of women across the nation.
But none will feel the hit quite as much as the roll call of exes that the red-headed royal has accumulated over the years.
The party-loving Prince has stolen the hearts of a plethora of genetically-blessed women over the years.
From sports presenter Natalie Pinkham to long-time love Chelsea Davy, we look back at the ones that got away – and lost out on the tiara to Meghan Markle.
As Prince Harry pops the question to Meghan Markle, we look back at the pop stars, society girls and lingerie models who missed out on his heart
2016: ELLIE GOULDING
Prince Harry was spotted getting very close to popstar Ellie Goulding at the Audi Polo challenge in Coworth Park, Berkshire, in 2016.
Onlookers said the pair were ‘all over each other’ and one claimed they appeared to share a kiss under a blanket.
Prince Harry was spotted getting very close to popstar Ellie Goulding just before he and Meghan became an item
The insider, who is close to Harry’s social circles, said that after the polo there was a late night party where picture-taking was banned to put the celebrities at ease.
‘Harry was really going for it after the polo – he was drinking and dancing,’ the source told The Sun.
‘They were part of a wider group including Tom Hardy but Harry and Ellie only had eyes for each other all night – they spent a lot of time sitting together under blankets.
‘They were seen having a kiss before Harry had to go because he was playing polo the next day. Ellie left about five minutes later.’
Harry and Ellie have been friends since they met after Harry’s Invictus Games in 2014 but are said to have been exchanging flirtatious texts.
She was asked to perform at Harry’s 30th birthday in September and before singing at the Royal Wedding in 2011 said of the Duke and Duchess of Cambridge: ‘I’m friends with them, so it’s not like it’s awkward because I don’t know them. So that’s fine.’
Harry and Ellie have been friends since they met after Harry’s Invictus Games in 2014
2015: JENNA COLEMAN
Prior to Meghan, Prince Harry’s last rumoured fling was Doctor Who star Jenna Coleman, who 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 29-year-old actress by the hand for a private chat after the Audi Polo Challenge at Coworth Park in Ascot on Saturday.
Photographs of their meeting showed Harry with his hand on her knee while the pair leant in on a number occasions and shared several jokes.
One onlooker told The Sun: ‘It looked like they were really enjoying each other’s company.’
While Harry had been single for almost two years after splitting with actress Cressida Bonas, Miss Coleman was dating Game of Thrones star Richard Madden.
A witness said Harry and Jenna were ‘sitting very close, laughing lots and touching each other. I had no idea she had a boyfriend until afterwards, but I don’t think he would have been very happy to see this’.
Harry had earlier been playing polo in aid of three charities, Centre Point, Child Bereavement UK and WellChild. Harry stayed on and went to the star-studded party afterwards.
2014: CRESSIDA BONAS
As Prince Harry’s most recent serious ex, actress and society girl Cressida Bonas was the woman presumed to become Prince Harry’s wife.
However, in 2014, the pair split and the thespian chose to remain dignified about why exactly the pair parted ways.
The months leading up to her split from Harry saw rumours hit fever pitch that the pair would imminently announce plans to marry.
Cressida Bonas was the woman presumed to become Prince Harry’s wife before they split in 2014
With a wedding thought to be on the way, the Duchess of Cambridge was even said to be helping shy Cressie learn how to handle to the intensity of the Royal spotlight.
But the actress later dismissed all that as mere ‘noise’, explaining in an interview: ‘All that stuff is not real. It’s really important to remember that all it is noise, noise that can be very loud at times.’
Cressida certainly had all the makings of a princess; she is friends with both Princess Beatrice and Eugenie, joining the former in the world record attempt to complete the London Marathon in a human caterpillar in 2010, while the latter is said to have introduced her to Harry.
She is the daughter of renowned Sixties It girl Lady Mary Gaye Curzon (whose father was the 6th Earl Howe) and Old Harrovian Jeffrey Bonas (her mother’s third husband) owns a fabric company called MacCulloch & Wallis.
Her parents have racked up six marriages between them so Cressida has a number of half brothers and sisters including soon-to-be a Branson, Isabella, who was once admired by Prince William, and Gabriella Wilde, a model for Burberry.
Cressida certainly had all the makings of a princess; she is the daughter of renowned Sixties It girl Lady Mary Gaye Curzon and Old Harrovian Jeffrey Bonas
Following her parent’s separation, Cressida continued to enjoy a privileged upbringing as her bohemian mother then married multi-millionaire Christopher Shaw.
Cressida attended £30,000-a-year Stowe School in Buckingham where she showed a flair for acting as well as sport.
She was said to be one of the most popular girls at the sixth form because of her zest for fun and free spirit.
She then attended Leeds University where she studied for a degree in dance and had another boyfriend with royal connections – Harry Wentworth-Stanley – whose stepfather, George Milford Haven, is a cousin of the Queen.
Dancing is the blonde’s passion and she went on to study contemporary dance at The Trinity Laban Conservatoire of Music and Dance in Greenwich.
Having grown up surrounded by a family of what she calls thespians and drama lovers, becoming an actress has long been Cressie’s dream.
Now, after studying drama and dance, she bagged herself a role in Tulip Fever, alongside Judi Dench, and supermodel-turned-actress Cara Delevingne, and has taken the fashion world by storm.
2012: MOLLIE KING
Mollie and Harry first met at a polo match in 2010 and were pictured partying together at Public nightclub and karaoke bar Bunga Bunga in London.
The 24-year-old singer – who split from male model David Gandy earlier that year – and Harry were allegedly set up by his cousin Zara Phillips, who is a friend of the pop star’s Saturdays bandmate Una Healy.
Mollie had previously remained very cryptic about the reports that she was in a relationship with the royal.
Mollie and Harry first met at a polo match in 2010 and were pictured partying together at nightclubs
2010: FLORENCE BRUDENELL-BRUCE
According to friends, Ms Brudenell-Bruce, who was Harry’s first girlfriend following his split from Chelsy Davy in 2011, found the attention that came with dating a royal hard to deal with.
‘Henry has been around a long time,’ a source was quoted as saying at the time. ‘Harry was more of an affair. Flee hated all the press attention she got when she was dating Harry.
‘She really liked him but she was embarrassed by being splashed all over the papers.’
Ms Brudenell-Bruce was Harry’s first girlfriend following his split from Chelsy Davy in 2011
The lingerie model and society star also had a high profile romance with Formula 1 star Jenson Button.
The 32-year-old is the daughter of Ernest Brudenell-Bruce, 3rd Marquess of Ailesbury, and was romantically linked to Prince Harry before marrying Mr St. George in June 2013.
2009: CAROLINE FLACK
X Factor host Caroline Flack told how she was once ‘Prince Harry’s bit of rough’, revealing that she dated the royal before her romance with One Direction star Harry Styles.
The television presenter said she began seeing Prince Harry in 2009 after the pair were introduced via a mutual friend.
However, she said that they were forced to call off their relationship after the ‘story got out’, and two years later she shocked fans by dating a then 17-year-old Harry Styles, who was 14 years her junior.
Details of her romances with both Prince Harry and the One Direction emerged in her autobiography, Storm in a C Cup.
X Factor host Caroline Flack told how she was once ‘Prince Harry’s bit of rough’
In an extract, the Norfolk-born star reveals how she ‘perked up’ after being introduced to Prince Harry, 31, by their mutual friend Natalie Pinkham, a Formula One correspondent for Sky Sports.
The pair met during an organised night out by Ms Pinkham, which came just after Flack had split from a former boyfriend.
She said: ‘I knew she was friends with Prince Harry, and I’d never met him, so I thought, “Oh that’s quite exciting”, and for a moment I perked up.
‘To meet a prince is so unlikely it would be weird not to acknowledge it.’
She said the pair began seeing each other, being photographed out together and that on a personal level she ‘really liked him’.
But she added: ‘However, once the story got out, that was it. We had to stop seeing each other.
‘I was no longer Caroline Flack, TV presenter, I was Caroline Flack, Prince Harry’s bit of rough.’
2004-2010: CHELSEA DAVY
As one of his longest-standing girlfriends, Chelsea was also lined up to be Prince Harry’s wife before they split in 2010.
The 32-year-old businesswoman, currently promoting an ethical jewellery brand, recently lifted the lid on what it feels like to date the prince, calling the intense media interest ‘scary’.
Chelsea Davy was also lined up to be Prince Harry’s wife before they split in 2010
On and off with Harry for the best part of seven years, Zimbabwe-born Davy revealed that she ‘couldn’t cope’ with the attention and eventually retreated back to Africa for calm.
In an interview with the Times, Davy revealed that being chased by photographers desperate to capture images of the couple together was terrifying.
Harry and Chelsea were on and off again for the best part of seven years
When the couple split in 2010, she says she retreated once again to her native Zimbabwe
She said: ‘It was so full-on: crazy and scary and uncomfortable. I found it very difficult when it was bad. I couldn’t cope.’
The former lawyer describes herself as ‘just a normal kid’ and says it was ‘tough’ to go through such chases at such a young age, saying: ‘I was trying to be a normal kid and it was horrible.’
After first meeting while she was a teenager at Cheltenham and then getting together during Prince Harry’s gap year in Cape Town, Davy returned to the UK to study in Leeds and be closer to the young royal.
Despite going on to establish a highly prized career at solicitor’s firm Allen & Overy, Chelsy was branded ‘a party girl’ by the media for her love of socialising.
She concedes she did nothing to correct the image and admits to ‘going out and partying a lot’.
When the couple split in 2010, she says she retreated once again to her native Zimbabwe unable to handle the break-up headlines. ‘It was nuts,’ she says. ‘That’s also why I wanted to go back to Africa. Now it’s calm, it’s fine.’
Chelsy, whose mother Beverley Donald is former Miss Rhodesia 1973, now divides her time between Zimbabwe, where her family is based, her jewellery mine in Zambia and west London – where she has a home in Chelsea.
She says she’ll always ‘be good friends’ with Harry and indeed remained so much a part of the royal circle that she was invited to William and Kate’s wedding in 2011.
She’s happy to be back in the media spotlight once more though, this time launching her new venture, an ethical beauty range.
The African-based jewellery company, Aya, making pieces with gems mined in Zambia. Of the range, she has said: ‘Aya is not a charity, it is a luxury brand of beautiful top quality stones and solid gold. But it won’t neglect the communities from where they are sourced.’
2003: NATALIE PINKHAM
Rumours of Natalie and Harry’s liaison started to whirl in 2006 after pictures surfaced of the pair and a source reported at the time that Harry was ‘absolutely infatuated with Natalie’.
Yet the relationship didn’t blossom further and she went on to marry Endemol executive Owain Walbyoff and the pair have a one-year-old baby boy.
The duo, who mix in the same circles, have remained close friends ever since.
Rumours of Natalie Pinkham and Harry’s liaison started to whirl in 2006 after pictures surfaced of the pair
2009: ASTRID HARBORD
Party-loving Astrid – who with her sister Davina has been dubbed one half of the ‘The hardcore sisters’ – was spotted in the back of a car with Harry entering Clarence House by a rear gate in the early hours of the morning in 2009.
A month later it emerged that Harry had attended an illegal rave with the Harbord sisters and 400 other revellers in a repossessed office block in Whitechapel, East London, and the prince left the ‘Dress2Sweat’ event at 1.30am with Miss Harbord.
Astrid, a history graduate from Bristol University who works in hotel PR, is also at the centre of William and Harry’s set and was a guest at the royal wedding.
Party-loving Astrid Harbord was spotted in the back of a car with Harry entering Clarence House by a rear gate in the early hours of the morning in 2009