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Prince Harry's dating history as he reveals mystery 'older woman' took his virginity

Prince Harry's dating history
Prince Harry and former girlfriends Cressida Bonas and Chelsy Davy. (Getty Images)

Prince Harry has detailed in his new memoir, Spare, the circumstances in which he lost his virginity. He claims the "humiliating experience" happened in a field outside a "very busy pub" when he was 17.

He said he lost his virginity with an older woman who treated him like a "young stallion".

"I mounted her quickly," he described, "after which she spanked my ass and sent me away.

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"One of my many mistakes was letting it happen in a field, just behind a very busy pub. No doubt someone had seen us."

Snippets of Harry's memoir were leaked last week, but since Spare was officially released yesterday, readers have been treated to never-before-seen insight straight from the "young stallion's" mouth about his romantic life.

Yahoo UK explains all of Harry's revelations about his love life and looks back at all the people Harry has been romantically linked to over the years.

Chelsy Davy

Davy was Harry's longest previous romantic relationship running on and off from 2004 until 2010. It was widely reported that the pair met in Cape Town, while Harry was on his gap year, but he revealed in Spare he had actually met her before that, and they reconnected while he was in Africa in 2004.

He discussed the difference in their relationship whilst they spent time in Africa together versus in the UK, where he recommended to Davy she treat press intrusion like a "chronic illness".

He explains that the pair finally broke up in 2010, and the reasons why they felt it wouldn't go the distance: a lack of privacy and believing she would have to change to fit into what life in the Royal Family entails.

WINDSOR, ENGLAND - MAY 5:  Prince Harry and girlfriend Chelsy Davy attend a service of remembrance and thanksgiving at the Holy Trinity Church on May 5 2008 in Windsor.  (Photo by Anwar Hussein/WireImage)
Chelsy Davy and Harry attending a remembrance service together in 2008. (Getty Images)

"The whole world isn’t made to put up with constant scrutiny, and I don’t know if Chels could bear it, and I couldn’t ask her to," he wrote.

He also claimed that at one time the paparazzi even placed a tracking device on her car, which made her want to put "freedom first".

"Chels insisted that she was not sure if she was prepared for all of that. A whole life with someone on your heels? What could I say to her? I would miss her very much, but I understood she put her freedom first. If I had the choice, I’d want to live like that as well."

Florence Brudenell-Bruce

ASCOT, ENGLAND - JUNE 20:  Florence Brudenell-Bruce attends day 2 of Royal Ascot 2012 at Ascot Racecourse on June 20, 2012 in Ascot, United Kingdom. (Photo by Samir Hussein/WireImage)
Florence Brudenell-Bruce at Royal Ascot in 2012. (Getty Images)

Until Spare's release, the relationship between Florence Brudenell-Bruce and Prince Harry had never been officially confirmed.

After what he described as an "idyllic" few weeks with the model and actress in 2011, news of their relationship found its way to the press, and "down came the curtain on our idyll."

Harry also revealed that despite him trying to persuade "Flea" as she is nicknamed to "talk it over", she firmly said no and he later found out from a friend her mother had dissuaded her from continuing the relationship.

"It was Flea’s mother who told her to end things," he explained, "who warned her that the press would destroy her life. 'They’ll hound you to the gates of Hell', her mother said. 'Yeah', I told the friend. 'Mums do know best.'"

Brudenell-Bruce married multi-millionaire Henry St. George two years later.

Cressida Bonas

LONDON, ENGLAND - MARCH 07:  Cressida Bonas and Prince Harry attend We Day UK, a charity event to bring young people together at Wembley Arena on March 7, 2014 in London, England.  (Photo by Karwai Tang/WireImage)
Cressida Bonas and Prince Harry attend a charity event at Wembley Arena in 2014. (Getty Images)

Harry opened up about his relationship with budding actress Cressida Bonas in Spare too. He explains that the pair were introduced by his cousin at a music festival and that despite the fact that he was "heartbroken" at the time "there were sparks."

During their first date Bonas opened up to him about her life and "dreams".

"She told me about her life, her family, her dreams. She wanted to be an actress. She was so soft-spoken and shy, acting was the last profession I’d have imagined for her, and I said so. But she confessed that it made her feel alive. Free. She made it sound like flying."

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Harry also divulged that because of his military career he didn't have much spare time and could only meet up with Bonas during the weekends and that after he returned from his second tour of duty, the couple had to restart from the beginning because he was so changed from the experience.

"Can’t have a reunion with someone you don’t know," he wrote. "If we wanted to keep seeing each other – and I certainly did – we’d have to start again."

Harry also explains how news of their relationship was broken by the press after they had already dated for two years, and how Bonas was the first person he was able to cry with about his mother's death since Diana's burial, something for which he was "indebted" to her.

WINDSOR, ENGLAND - MAY 19:  Cressida Bonas (L) attends the wedding of Prince Harry to Ms Meghan Markle at St George's Chapel, Windsor Castle on May 19, 2018 in Windsor, England. Prince Henry Charles Albert David of Wales marries Ms. Meghan Markle in a service at St George's Chapel inside the grounds of Windsor Castle. Among the guests were 2200 members of the public, the royal family and Ms. Markle's Mother Doria Ragland.  (Photo by Chris Jackson/Getty Images)
Cressida Bonas and Harry remained friendly after their break-up, with Bonas attending his 2018 wedding to Meghan. (Getty Images)

"Wiping my eyes, I thanked her," he wrote. "She was the first person to help me across that barrier, to help me unleash the tears. It was cathartic, it accelerated our bond, and added an element rare in past relationships: immense gratitude. I was indebted to Cress."

Harry also wrote that when he finally ended the relationship because it wasn't "love everlasting" he thought: "She helped me cry. And now I’m leaving her in tears."

In 2017, Bonas opened up to BBC Radio 4 about feeling "pigeonholed" after being in such a public relationship.

"It’s incredibly frustrating, especially in the industry that I’m in. But you know, it is the way it is," she said.

Meghan Markle

WINDSOR, UNITED KINGDOM - MAY 19: Britain's Prince Harry, Duke of Sussex and his wife Meghan, Duchess of Sussex leave from the West Door of St George's Chapel, Windsor Castle, in Windsor on May 19, 2018 in Windsor, England. (Photo by  Ben STANSALL - WPA Pool/Getty Images)
Harry and Meghan after their wedding ceremony in Windsor, 2018. (Getty Images)

The woman who would become Harry's wife and the mother of his two children, Meghan Markle, is of course a big focus in Harry's memoir.

In their recent Netflix documentary they revealed that they actually met over Instagram, before embarking on a whirlwind, long-distance romance, which Harry details in Spare. He wrote he had "never seen anyone as beautiful" as Meghan and noted once they started chatting his "thumbs were cramping" he was trying to text so quickly.

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"I couldn’t type fast enough. My thumbs were cramping," he detailed, "there was so much to say, we had so much in common, though we came from such different worlds. She was American, I was British. She was well-educated, I was decidedly not. She was free as a bird, I was in a gilded cage."

Their relationship went public in October 2016, and a month later Harry released an unprecedented and blistering statement about how his new partner was being treated in the press and online.

"It is not right that a few months into a relationship with him that Ms. Markle should be subjected to such a storm," it said.

The pair married in May 2018 and welcomed their first child, Archie the following year. As the pressure of life in the public eye became overwhelming for the couple, they stepped back from royal duties in 2020 and since living in California, have had a daughter: Lilibet, inspired by the Queen Elizabeth's childhood nickname.

Caroline Flack

LONDON, ENGLAND - JUNE 07: Caroline Flack arrives for the Glamour Women Of The Year Awards on June 7, 2016 in London, United Kingdom.  (Photo by Mike Marsland/Mike Marsland/WireImage)
Caroline Flack at the Glamour Women Of The Year Awards in 2016. (Getty Images)

Caroline Flack is also discussed in Harry's new memoir, in which he refers to their romantic relationship as "tainted".

The pair first met in 2009 when they were introduced by a mutual friend, but any sparks of romance between them were quickly extinguished by severe press intrusion that let to paparazzi camping outside her parent's home and deeming Flack, Harry's "bit of rough".

"I continued to see Flack on and off," after the relationship had been made public, Harry wrote, "but we didn’t feel free any more. We kept on, I think, because we genuinely enjoyed each other’s company, and because we didn’t want to admit defeat at the hands of these arseholes. But the relationship was tainted, irredeemably, and in time we agreed that it just wasn’t worth the grief and harassment."

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The Duke of Sussex also touched on how he felt when he heard the news that Flack had taken her own life, saying it was "impossible" when he had first known her to imagine this happening.

"She’d been so light and funny that night we met. The definition of carefree. It would’ve been impossible then to imagine this outcome."

He then made a covert reference to Meghan's own fleeting suicidal feelings. "I told myself it was an important reminder. I wasn’t being over-dramatic, I wasn’t warning about things that would never happen."

Natalie Pinkham

Although the pair never confirmed a romance, it has long been rumoured that Pinkham and Harry were once involved back in 2003, when the prince was 19 and she was 26.

Britain's Prince Harry talks to British TV and radio presenter Natalie Pinkham on the trading floor as he attends BGC Partners' Charity Day in London, on September 12, 2011. Britain's Prince Harry, co-founder and Patron of Sentebale, today attended BGC Partners’ Charity Day, which is held each year to commemorate the company’s 658 employees who lost their lives in the 9/11 attacks on the World Trade Center. Prince Harry helped raise money for Sentebale and other charities by supporting BGC Partners in deals on the trading floor. AFP PHOTO / PAUL GROVER / POOL (Photo credit should read PAUL GROVER/AFP via Getty Images)
Natalie Pinkham and Prince Harry at the BGC Partners day in 2011, long after they were romantically linked they remained friends. (Getty Images)

The pair have enjoyed a long-standing friendship, and in 2009 it was reported that after his split from a later girlfriend, he even turned to Pinkham for advice and support.

Pinkham – a television presenter – is now married to Owain Walbyoff, Managing Director of Endemol Games, and they have two children: Wilfred and Willow.

Astrid Harbord

LONDON, ENGLAND - SEPTEMBER 29: Princess Beatrice of York and Astrid Harbord attend the 8th annual Lady Garden Foundation Ladies Lunch at Langan's Brasserie on September 29, 2022 in London, England. (Photo by David M. Benett/Dave Benett/Getty Images)
Astrid Harbord isn't just friends with Kate, but acquainted with other members of the Royal Family, like Princess Beatrice – pictured here at an event in September 2022. (Getty Images)

For a brief time in 2009, Harry was linked to one of Kate's friends, Astrid Harbord. While he was on the outs with Davy he was spotted hitting the town with Harbord in London and they were reported to go home to Clarence House together in the early hours of the morning.

Mollie King

LONDON, ENGLAND - FEBRUARY 08: (EDITORIAL USE ONLY)  Mollie King arrives at The BRIT Awards 2022 at The O2 Arena on February 8, 2022 in London, England. (Photo by David M. Benett/Dave Benett/Getty Images)
Mollie King arrives at The BRIT Awards 2022. (Getty Images)

The member of the pop band The Saturdays was romantically involved with Prince Harry briefly in 2012. King admitted the pair had dated after they met at the Asprey World Class Cup, but it was reported that this public comment didn't go well down with Harry, who ended things shortly after.

Ellie Goulding

LONDON, ENGLAND - SEPTEMBER 14:  Prince Harry with Ellie Goulding backstage at the Invictus Games Closing Ceremony during the Invictus Games at Queen Elizabeth park on September 14, 2014 in London, England. The International sports event for 'wounded warriors', presented by Jaguar Land Rover was an idea developed by Prince Harry after he visited the Warrior Games in Colorado USA. The four day event has brought together thirteen teams from around the world to compete in nine events such as wheelchair basketball and sitting volleyball.  (Photo by Chris Jackson/Getty Images)
Ellie Goulding backstage with Prince Harry at the 2014 Invictus Games. (Getty Images)

Another romance from the rumour mill was with popstar Ellie Goulding, after they were reported to be very cosy at the Audi Polo Challenge in 2015.

They were said to be seen snuggled under a blanket together and spotted kissing, however neither party ever confirmed that they were more than friends.

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