Prince Harry’s love life could have taken a very different turn before he met Meghan Markle, according to comedian Katherine Ryan.

The 40-year-old royal was single at the time and struggling to find someone willing to take on the challenges of life within the royal family.

Speaking recently, Katherine, 41, revealed that she once tried to set up Harry with Keeping Up with the Kardashians star Kourtney Kardashian, 46, during a party in London.

How Prince Harry and Kourtney Kardashian nearly crossed paths

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Katherine recalled attending a party at the home of comedian Jimmy Carr in 2016. Among the guests were Princess Beatrice and, unexpectedly, Kourtney.

“I walked in and saw Kourtney Kardashian with Princess Beatrice,” Katherine explained.

She admitted being starstruck, saying: “I went straight over to her because I knew who she was. I’m so invested in the Kardashians and their reality show.”

At the time, Kourtney was still navigating an on-and-off relationship with Scott Disick, the father of her three children.

Katherine shared: “I said, ‘You need to leave Scott.’ And she said, ‘How can I? He’s in my house right now.’ I told her, ‘Don’t go back to the house. You need to leave him.'”

Katherine’s bold matchmaking idea

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As the conversation continued, Kourtney asked who she could even date instead.

Katherine didn’t hesitate: “Prince Harry, maybe?”

The comedian said she thought it made perfect sense: two famous families, both accustomed to life in the spotlight, uniting in one of the most surprising romances of the decade.

At the time, Harry had been open about his difficulties finding love. In a rare interview, he admitted: “I’m not so much searching for someone to fulfil the role, but finding someone who would be willing to take it on.”

Katherine joked: “She was right there in the UK. It seemed obvious.”

What happened next

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It’s not clear whether Katherine followed through with her matchmaking idea. There’s no suggestion that Harry and Kourtney ever met or spoke.

Instead, later that year, Harry would go on to meet Meghan Markle, then best known for her role in Suits.

In his memoir Spare, Harry revealed that he first saw Meghan’s photograph on Instagram. Although he and Meghan previously said they met on a “blind date,” Harry admitted he had admired her photos before agreeing to the introduction.

Their matchmaker is widely believed to be Violet von Westenholz, a friend of Harry’s who worked in PR at Ralph Lauren, although other reports have suggested fashion designer Misha Nonoo.

How different history might have been

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The revelation has left fans wondering how different royal history could have been if Katherine had successfully played Cupid.

Instead of Meghan, Harry could have found himself at the centre of a transatlantic media storm involving the Kardashians.

Despite the near-miss, Harry’s relationship with Meghan moved quickly, with the couple announcing their engagement in November 2017 and marrying at Windsor Castle the following May.

As for Kourtney, she went on to marry Blink-182 drummer Travis Barker in 2022, after a whirlwind romance.

Meanwhile, Harry and Meghan are raising their two children, Prince Archie and Princess Lilibet, in California, far from the royal spotlight.