The Duke of Sussex has not only touched upon his family tensions and mental health battle in his memoir, Spare, but he has also given royal watchers a candid insight into the breakdown of his former relationships.
His romance with actress Cressida Bonas was his second most high-profile one to date after he cut ties with his first girlfriend Chelsy Davy.
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Prince Harry started dating Cressida in 2012 after being introduced by his cousin Princess Eugenie. The former couple shared a lust for life and they were snapped together on various occasions, appearing the perfect pair.
But as rumours of a royal engagement escalated, Cressida is said to have become increasingly overwhelmed by the public attention. While the pair split in 2014, they proved they are still on good terms, with Cressida attending Harry and Meghan's wedding in 2018.
Shortly before his deployment in Afghanistan in late 2012, Harry was photographed naked while playing with friends in Las Vegas. After the incident, he explained how he apologised to her for "embarrassing her".
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"After hearing my careful and abashed explanation, she came to the same conclusion. I'd been a dummy, not a debaucher. I apologised for embarrassing her," he wrote.
© Photo: Getty ImagesPrince Harry dated Cressida for nearly three years
They endured a long-distance relationship when Harry went to war. However, when the Duke returned home one weekend, he recounted there was some "some distance" and "some stiffness" between them.
Both she and Princess Eugenie told him he looked in some way like a different person, which he described as frightening and off-putting for Cressida.
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Later that month, the former couple went on a skiing trip to Kazakhstan where Harry broke down in tears when talking about the loss of his mother to Cressida – he said this was the first time he cried since Princess Diana's burial.
© Photo: Getty ImagesThe former couple endured a long-distance relationship
It wasn't until then, Harry decided they weren't a match. "There was massive affection, deep and abiding loyalty – but not love everlasting," he shared.
Upon returning home, Harry was torn over what to do. He added: "The day after we got home from Kazakhstan I phoned a mate, who was also close with Cress. I told him about my feelings and asked for advice. Without hesitation the mate said that if it was done it must be done quickly. So I drove straight over to see Cress."
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Explaining the situation, Cressida agreed. "None of it seemed to surprise her," he reflected. "These things had been on her mind as well."
© Photo: Getty ImagesCressida seen attending Prince Harry and Meghan Markle's wedding in 2018
"'I've learned so much from you, Cress'," he told her. "She nodded. She looked at the floor, tears running down her cheeks. Damn, I thought. She helped me cry. And now I'm leaving her in tears."
In the book, Harry also revealed how he considered marrying the British actress, and that his brother Prince William and sister-in-law Kate had "mentioned, pointedly, repeatedly, how much they liked Cressida".
Cressida, 33, has since found love with husband Harry Wentworth-Stanley. The duo have now welcomed their first child together.
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