Before Prince Harry settled down with his wife Meghan Markle, the young royal was a lad-about-town and a big hit with the ladies – including Mollie King and Camilla Thurlow

Back in the days of his bachelorhood, Prince Harry had many romances with well-known faces.

Throughout his teen years and twenties, the young prince was regularly papped partying until the early hours and was seen getting up to mischief with his mates. Harry, who tied the knot with Meghan Markle in 2018, used to be a big hit with the ladies before he ditched pints for parenthood and welcomed two children.

In his autobiography Spare, Harry touched on his misspent youth and dalliances with the elite – including the mystery ‘beautiful older woman’ he lost his virginity to in the countryside, and his early relationship with Chelsy Davy who made him ‘really happy’. Here, the Mirror takes a look at his forgotten loves and rumoured flings…

Harry’s first sexual partner was an unidentified “beautiful older woman” who took his virginity in a field behind a busy pub. In his memoir Spare, Harry wrote: “I suspected he was referring to my recent loss of virginity, a humiliating episode with an older woman who liked macho horses and who treated me like a young stallion. I mounted her quickly, after which she spanked my ass and sent me away.”

His mature lover has been a mystery for decades, but some believed that Liz Hurley may have been the one. Shutting down accusations, Liz told the Times: “No. Not me. Absolutely not.”

Natalie Pinkham

Apparently Natalie Pinkham sent Harry ‘head over heels’ in love ( 
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AFP/Getty Images)
Harry was just 19 years old when he’s said to have fallen for his long-time pal, Formula One Sky Sports correspondent Natalie Pinkham. The royal was apparently ‘head over heels’ for Natalie and the pair are believed to have remained firm friends until he met Meghan. Natalie didn’t make the wedding invite list, although sources said she approved of her former ‘drinking buddy’s’ new romance, insisting: “Natalie feels Meghan is the sensible soulmate who will tame Harry’s wild side.”

Chelsy Davy

Chelsy and Harry were dating on and off for seven years in total ( 
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ExpressStar)
Chelsy Davy was Prince Harry’s first serious girlfriend, after the pair met while attending the Stowe School in Buckinghamshire. The couple were in an on-off relationship between 2004 and 2011, during which time Chelsy met the late Queen and accompanied Harry to William and Kate’s wedding. But it seems the late monarch wasn’t a fan of Chelsy’s free-spirited lifestyle, and ultimately this led to their separation.

In Harry’s memoir Spare, he wrote that Chelsy made him “really happy” but it wasn’t enough for the relationship to last. “I couldn’t help what my grandmother thought about it. Or the people. And the last thing I wanted was for Chels to change to please them,” he wrote.

Chelsy has also spoken out about the immense pressure of being in the public eye. “It was so full-on: crazy and scary and uncomfortable,” she told the Times. “I found it very difficult when it was bad. I couldn’t cope. I was young, I was trying to be a normal kid and it was horrible.” Still, their bond and friendship appeared to stay strong as Chelsy was spotted at Harry and Meghan’s wedding in 2018.

Astrid Harbord

Harry was 24 when the pair reportedly had a brief relationship ( 
Image:
PA)

Astrid Harbord pictured with Princess Beatrice in 2022 ( 
Image:
Dave Benett/Getty Images)

Princess Kate’s friend Astrid Harbord was briefly linked to Harry in 2009, when he was on a break with Chelsy. The pair were spotted hanging out in London and reportedly spent a night at a club before heading back to Clarence House at 3am. While Harry and Astrid never confirmed nor denied the rumours, they were pictured attending multiple events over the years. However, it was said that he cut ties with the socialite when things got serious between him and Meghan.

Caroline Flack

Caroline Flack was introduced to Harry by Natalie Pinkham ( 
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Getty Images)

She wrote about their brief fling in her autobiography ( 
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DFL / Splash News)
The late Love Island host met the prince through mutual friend Natalie Pinkham on a night out in 2009, and they hit it straight off. “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,” Caroline Flack recalled of their meeting in her book.

“So I was just sitting there and he arrived with a few others in tow and we all spent the evening chatting and laughing.” But once word got out, the party was off. “We had to stop seeing each other,” she continued. “I was no longer Caroline Flack, TV presenter, I was Caroline Flack, Prince Harry’s bit of rough.”

Florence Brudenell

Model Florence has openly spoke about their break-up ( 
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Dave Benett/Getty Images)

She feels very fortunate that the pair never worked out ( 
Image:
Channel 4)
Harry and model Florence Brudenell – a daughter of the Earl of Cardigan – reportedly dated in 2011. But it’s believed Florence actually ended things with Harry, and feels “lucky” that she did. She told Stella magazine: “My privacy ended abruptly, and the scrutiny began. A new story would appear almost every day in the press, my school friends were interrogated and there were photographers outside my front door.”

Cressida Bonas

Cressida was in a relationship with Harry for two years from 2012 ( 
Image:
WireImage)
Harry dated Cressida Bonas from 2012 through to 2014 after being introduced by his cousins Princess Eugenie and Princess Beatrice. Actress Cressida, who has worked with Burberry and Mulberry, spent two years with Harry before the pair amicably split. It is alleged that Cressida couldn’t cope with the public scrutiny that came with being Harry’s girlfriend.

Mollie King

In 2012, The Saturdays’ Mollie King was reported to have enjoyed a string of secret dates with Harry after meeting at the Asprey World Class Cup at Surrey’s Hurtwood Polo Club. Radio One star Mollie initially tried to throw fans off the scent by insisting the then third-in-line to the throne was ‘out of her league’.

She said: “No, I’m not going out with him – I’m serious. Everyone wants to believe it because he’s royalty. Everyone would like it to be true but it’s not. He’s very out of my league, come on.”

Eventually, she came clean, telling Closer magazine: “Yes, I have met Harry, and we did go out for a drink. But a lot of the times I’m linked to men, I haven’t even met them!” Harry is rumoured to have broken things off amid fears that Mollie was being too open.

Former Saturdays star Mollie King was another alleged fling ( 
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Gareth Cattermole/Getty Images)

The pair were allegedly ‘all over each other’ and very flirty ( 
Image:
getty)

Ellie Goulding

In 2016, Harry and Ellie Goulding allegedly started exchanging flirty texts after their friendship ‘stepped up a gear’. The pair were said to have been “all over each other” at a polo match.

A source said: “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 was overheard on the way out telling some friends how much he liked her.”

Lauren Pope

Lauren Pope was once linked with Prince Harry ( 
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GETTY)

Lauren and Harry apparently danced the night away ( 
Image:
WENN)
Lauren Pope’s rise to fame could have come a lot sooner than TOWIE. The reality star apparently caught the Prince’s eye in February 2004 – years before she would become a star on The Only Way Is Essex.

The pair were said to have quickly bonded after dancing in a nightclub until 3am. Unfortunately, it just wasn’t to be and after the story broke, Harry is said to have cut all ties with Lauren.

Catherine Ommanney

Real Housewives star Catherine said Harry kissed her ( 
Image:
WireImage)
Real Housewives of DC star Catherine Ommanney met Harry in 2006, and according to her, they sealed the deal with a kiss on a night out. “Harry lifted me off of the floor and kissed me,” she confessed to Mail on Sunday. “It was a long and lovely kiss. He did kiss me again. It wasn’t just once.” The pair allegedly enjoyed a string of dates before things fizzled out.

Camilla Thurlow