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.”

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 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.

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.

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