Prince Harry was, as he called himself, the “spare” of the royal family. While Prince William has spent much of his life preparing for a role as the future king, Harry always had a different future. Sure, it wasn’t a future without money or fame, but it wasn’t for him. 

Before meeting Meghan Markle, Harry had several girlfriends. Some were more serious than others, and in his book, Spare, he even revealed when he lost his virginity.

But even though it has been many years since the days of girlfriends and romances, one girlfriend, in particular, appears to have stuck by the royal life she would’ve had if she married Harry. Just months ago, she suddenly appeared alongside some of her ex-boyfriend’s family members, but her timing was probably not the best. 

Even though Harry’s book included some serious and sometimes tragic chapters of his life, he also took the time to write about lighter themes, including his former romances and girlfriends.

Harry even detailed how he lost his virginity to an “older woman,” whose identity has now reportedly been revealed.

Prince Harry – girlfriend Chelsy Davy

Between 2004 and 2010, Harry was involved in one of his most extended relationships when he and Chelsy Davy formed a couple.

The two were said to have met when Harry was on his gap year in Cape Town, but in Spare, he revealed that they had met earlier and merely reconnected while visiting Africa in 2004.

Harry discussed their relationship, which he argued had two different sides: one from when they spent time together in Africa and one in the UK.

In 2010, the couple broke up, and Harry said the reason was a lack of privacy. Moreover, he felt Davy had to change to fit into royal life.

“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,” Harry wrote in Spare, claiming that the paparazzi had even placed a tracking device on her car.

As a result, Chelsy Davy felt she wanted “freedom first” rather than the very public life the future would hold with Harry.

“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.”

Throughout his life, Harry has seen what the British paparazzi can do to women entering the royal sphere. Princess Diana was one example, Kate Middleton another, and of course, his wife, Meghan Markle, came next. The press dug deep into each person’s private life, trying to find the “good stuff” – often terrible things that readers would flock to read.

Cressida Bonas
David M. Benett/Dave Benett/Getty Images for Elephant Family

The woman Harry dated after Chelsy Davy had the same feelings towards the press and thought that a life with that coverage was too much.

Two-year relationship with Cressida Bonas

A year after his breakup with Davy, Harry began dating Florence Brudenell-Bruce. However, it wasn’t until he released Spare that Harry confirmed his relationship with “Flea”.

They spent an “idyllic” few weeks together before the press started printing stories about the two. In the end, Harry revealed that Florence’s mother told her daughter to end the relationship.

Before Harry met Meghan Markle and settled down, he also dated Cressida Bonas. Unfortunately, the couple’s love story didn’t last, but ultimately, Harry and Cressida’s relationship became significant on a different level.

At the time, Harry had just started his career in the military. Naturally, he didn’t get to spend as much quality time with his then-girlfriend as he wanted, and she, at the same time, was working hard to become an actress.

Their relationship lasted for two years before the press found out about it.

In Spare, Harry revealed that Cressida was the first person he could cry in front of when speaking about his mother’s passing. He felt “indebted” to her.

“Wiping my eyes, I thanked her,” Harry stated. “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.”

Cressida Bonas
Max Mumby/Indigo/Getty Images

Harry and Cressida remained great friends. And when the Prince and Meghan Markle tied the knot in 2018, she attended the wedding.

Prince Harry’s ex Cressida Bonas joins royal family members to support Princess Eugenie

Not long after leaving the royal family for good, Harry and Meghan came out with massive criticism against The Firm. Through the infamous Oprah interview, the Netflix series, and Harry’s book, Spare, the Sussexes bashed many parts of royal life and the treatment they received.

Meanwhile, it appeared that Harry’s ex, Cressida, continued to be a part of royal life, at least in a tiny way. Back in the day, it was Harry’s cousin, Princess Eugenie, who had introduced him to Cressida. Eugenie and Cressida have been great friends for years. In November last year, Harry’s ex-girlfriend stepped out with Zara Tindall, daughter of Princess Anne, at The Anti Slavery Collective’s inaugural Winter Gala to support Eugenie.

Held at the Battersea Arts Centre, Cressida Bonas wore a strapless pink and red striped gown, and her trademark blonde hair is still as iconic as what royal fans remember when she dated Harry.

Cressida has been seen having a close bond with Princess Eugenie many times. When the princess gave birth to her first child, Cressida congratulated her on Instagram.

Dave Benett/Getty Images for The Anti Slavery Collective

Over the years, Harry was linked with several other women. But in the end, it was Suits actress Meghan Markle who stole his heart.

The revelations about his previous romances interested the readers of his book. But it was another, more intimate section that got all the attention.

Harry revealed and gave details of when and how he lost his virginity in his book – and now the woman he was with has given her side of the story.

Harry revealed in ‘Spare’ how he lost his virginity

The experience, at age 17, was quite something, with the prince detailing how he lost his virginity in a field behind a pub – with an older, horse-loving woman.

“A humiliating episode with an older woman who liked macho horses and who treated me like a young stallion,” Harry wrote about the experience, which occurred when he was a student at Eton in 2001.

“Quick ride, after which she’d smacked my rump and sent me off to graze. Among the many things about it that were wrong: It happened in a grassy field behind a busy pub. Obviously, someone had seen us.”

Of course, everyone wanted to know who the mystery woman was, and the British papers wasted no time before they started digging. One woman who was asked was a former model and passionate horsewoman, Suzannah Harvey. But in an interview with the Times, she denied it was her.

Initially, the identity of the woman Harry had first been with was kept a secret. Then, days ago, Sasha Walpole decided to step forward.

As soon as the tell-all book – which included Harry’s bombshell revelation about losing his virginity – was released, Sasha felt she had to tell her father that she was the one.

In an interview with The Sun, Walpole revealed that she had previously only told her mother about her intimate time with Harry. The pub behind which Harry said he lost his virginity was the Vine Tree Inn in Wiltshire.

Sasha Walpole steps forward as the “older woman”

“I am the woman who took Harry’s virginity. It was ­literally wham-bam between two friends. [It was] passionate and sparky because we shouldn’t have been doing it,” Walpole said.

She added: “We went outside, and both climbed a three-bar fence to the field. We were quite drunk at this point. I gave Harry a cigarette. I lit mine and then his. We finished our cigarettes – Marlboro Lights – and it just happened. He started to kiss me.”

Sasha added that neither of them said a word while it happened.

“It was exciting that it was happening. It was exciting that it was happening like the way it was. We were away for 15 minutes, but the [intercourse lasted] about five ­minutes,” she explained, saying that they had to go in separate directions back to the pub.

However, looking back, she realized it was “probably more obvious.”

“I went back over the fence through the garden. A lot of people were outside, as it was kicking-out time by the time we’d finished. My friends saw me and started laughing. I didn’t have my belt and it’s obvious when you come back a bit dishevelled from a field.”

She added: “We had been gone about 15 minutes, and it was long enough for the security to start worrying where he was.”


Sasha is only a couple of years older than Harry. She had worked at the stable at then-Prince Charles’ residence, Highgrove Gouse, and admitted that she and Harry were “mates.” At the time, Harry and Sasha had reportedly known each other for about two years.

Harry reportedly reached out to ex-girlfriends about writing ‘Spare’

The two had been drinking tequila and sambuca earlier during the night while celebrating Sasha’s birthday. After that, they never spoke again.

“Harry and I never texted or rang each other after that. I didn’t mind. I wasn’t embarrassed,” Sasha said.

Harry reportedly spoke to many of his old friends back in England, asking if they could help him write Spare.

But apparently, it wasn’t only friends Harry reached out to. According to the Sun, Harry sensationally even contacted some of his ex-girlfriends during the summer. The prince wanted help writing the book and reportedly asked his ex-girlfriends to open up about some intimate details regarding their relationships and his upbringing.

Two of his most famous girlfriends were Chelsy Davy and Cressida Bonas. It’s not known whether they were among the people Harry asked.

One source told The Sun that some of the people Harry reached out to thought his request was “ironic,” not least because he, in the past, has asked his friends and close contacts not to speak about his private life in the media at all.

But though Harry asked, he is said to have been rejected several times.

Max Mumby/Indigo/Getty Images

“Friends and girlfriends were polite and said they would think about it but ultimately most said no,” a source told the paper.”

“Scandal has a habit of emerging eventually into the light”

“It was felt to be kind of ironic Harry would hit the roof if he ever had an inkling they spoke to the media, but now wants them to when he needs their help.”

Royal expert and journalist Robert Crampton wrote in The Times that Harry requesting help from his exes was a “high-risk strategy.”

“His mates, plus old flames Chelsy Davy and Cressida Bonas, have been souls of discretion thus far. But once they start talking, they might get a taste for it, especially when and if one of them falls on hard times. Scandal has a habit of emerging eventually into the light,” he wrote.

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