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Before Meghan Markle, there was Prince Harry‘s ex-girlfriend Cressida Bonas whom he dated from 2012 to 2014. In his bombshell 2023 memoir Spare, he recalled their first meeting as “painfully awkward.”
It was Harry’s cousin, Princess Eugenie that introduced the two. “I leaned in to give her a kiss, but my aim was off,” the Duke of Sussex wrote of his first date with the English actress. “She turned, I tried again on the return trip and we managed something like a graze.”
It obviously worked out after that. As Harry wrote: “But then came the good news. Cressida was game to try again.” Borderline cringe writing aside, the prince’s past relationship wasn’t that far from his current marriage, which is rumored to be ending.
As fans noticed, he does seem to have a type. Even his ex, Chelsy Davy was like Meghan in a way that she wasn’t interested in his royal background. “Unlike so many people I knew, she seemed wholly unconcerned with appearances, with propriety, with royalty,” he said in his book.
But it’s not just Harry; Cressida also seems to have a type. Did you know she ended up marrying another Harry?
Why Prince Harry And Cressida Bonas Broke Up
After getting past their awful first kiss, Cressida went on to help Harry with mourning his mom, Princess Diana, years after she died at a tragic car crash in 1997. In his tell-all, the Archewell co-founder revealed that his then-girlfriend had “just the right blend of curiosity and compassion” to ask him about his mom’s passing. He started to break down while answering her.
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.” But even though he feels “indebted” to her, their “massive affection, deep and abiding loyalty” was “not love everlasting.”
Like Meghan, the White House Farm star was also “clear about not wanting to take on the stresses of being a royal,” said the prince, noting that she wasn’t surprised when he broke things off with her. “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.”
Shortly before Harry’s deployment in Afghanistan in late 2012, he was notably photographed naked in Las Vegas, which he admitted to have mortified the Tulip Forever alum. “After hearing my careful and abashed explanation, she came to the same conclusion,” he said of its impact in their relationship.
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“I’d been a dummy, not a debaucher. I apologized for embarrassing her,” he continued. But after his return, he noticed “some distance” and “some stiffness” between them.
Prince Harry’s Ex Cressida Bonas Was At His Wedding To Meghan Markle
Due to the amicable split, Harry and Cressida remained on good terms that she was even present in his 2018 nuptials to Meghan (so was Chelsy). She even wrote about the “tricky” experience on the Spectator. “Last weekend I attended the royal wedding,” she wrote in the blog. “The invitation clearly stated that guests must wear hats. Yikes. I opted for a minimal feathered number — and can only hope I got it right.”
She went on to explain her weird relationship with hats. “Friends are starting to get married, which means the dilemma of British wedding attire. Hats,” Cressida confessed. “Why do I find hats so tricky? Tricky to wear, tricky to look at, and extremely tricky for the poor soul sitting in the pew behind.”
She added that “most of the time I avoid headgear” as “this can prompt disapproving looks from the older generations.” Well, she certainly looked beautiful in her simple feather headpiece as seen in the photo above. And two years later, she ended up getting married as well.
Prince Harry’s Ex Cressida Bonas Married A Man Named Harry
On July 25, 2020, Cressida tied the knot with property investor, Harry Wentworth-Stanley in an intimate ceremony in West Sussex. Similar to the prince’s background, this Harry is the son of the Marchioness of Milford Haven, Clare Husted Steel and her first husband, Nicholas Philip Wentworth-Stanley. Clare later remarried George Mountbatten, the fourth Marquess of Milford Haven.
In November 2022, the Wentworth-Stanleys welcomed their first child, Wilbur James Wentworth-Stanley. He was named after his father’s brother, James who passed away in 2006.
A month before that, Prince Harry’s other ex, Chelsy announced that she’d given birth to her first child with hotelier Sam Cutmore-Scott. They also welcomed a baby boy named Leo. Now, those are some interesting coincidences right there.
