Once upon a time. Before Prince Harry met wife Meghan Marklehe dated Cressida Bonas for two years.

The pair sparked a romance in 2012 after being introduced by Harry’s cousin Princess Eugenie. In his January 2023 memoir, Sparethe Duke of Sussex recalled a “painfully awkward” moment from their first date.

“I leaned in to give her a kiss, but my aim was off,” he wrote. “She turned, I tried again on the return trip and we managed something like a graze.” When the Prince called Eugenie to lament the less-than-smooth smooch, he learned that his cousin had already heard the story from Bonas.

“But then came the good news,” Harry continued. “Cressida was game to try again.”

With their lackluster first kiss behind them, the twosome continued to date for two more years. In Sparethe BetterUp CIO recalled the Bye Bye Man actress helping him mourn his mother Princess Diana‘s death years after the tragedy occured. (The late royal died at age 36 in an August 1997 car crash.)

During a 2014 ski trip to Kazakhstan, Harry’s then-girlfriend asked him about Diana with “just the right blend of curiosity and compassion.” While answering her, he started to cry.

The prince wrote that the intimate moment marked his first time crying about his mother’s death since her burial. “She was the first person to help me across that barrier, to help me unleash the tears,” he penned. “It was cathartic, it accelerated our bond and added an element rare in past relationships: immense gratitude.”

Despite feeling “indebted” to the model, the Archewell cofounder broke up with Bonas shortly after the vacation.

“There was massive affection, deep and abiding loyalty — but not love everlasting,” Harry wrote of their 2014 split, noting that Bonas had always been “clear about not wanting to take on the stresses of being a royal.”

He recalled that Bonas didn’t seem surprised when he told her he wanted to call it quits. “These things had been on her mind as well,” he said. “‘I’ve learned so much from you, Cress’. 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.”

Although their love story didn’t last, the exes have seemingly remained on good terms. Bonas attended Harry and Meghan’s 2018 nuptials, donning a bespoke Eponine London dress and pink feathered fascinator for the occasion. The actress wed Harry Wentworth-Stanley in 2020 and the pair welcomed son Wilbur in 2022.

Harry and Meghan, meanwhile, share son Archie and daughter Lilibet, born in 2019 and 2021, respectively.

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Keep scrolling for a look at Harry and Bonas’ relationship over the years: