Prince Harry and Kourtney Kardashian: The romance that never was before Meghan Markle

Prince Harry's love story with Meghan Markle almost had a very different beginning.

Years before the Duke of Sussex met his future wife, Harry was nearly introduced to reality television star Kourtney Kardashian in what could have been one of the most unexpected celebrity pairings.

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The surprising revelation came from Canadian comedian Katherine Ryan, who recently recalled trying to play matchmaker during a London party hosted by British comedian Jimmy Carr in 2016.

According to Ryan, she walked into the event and immediately spotted Kourtney chatting with Harry's cousin, Princess Beatrice. 

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As a longtime fan of the Kardashian family, Ryan struck up a conversation with the Poosh founder, who was still navigating her complicated relationship with longtime partner Scott Disick at the time.

"I walked in and saw her with Princess Beatrice," Ryan recalled. "I went straight over to her because I knew who she was. I'm so invested in the Kardashians and their reality show."

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Ryan said she encouraged Kourtney to move on from Disick, even after the reality star admitted he was waiting for her back at home.

"I said, 'You need to leave Scott,'" Ryan remembered. "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.'"

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When Kourtney asked who she should date instead, Ryan didn't hesitate. "Prince Harry, maybe?" she suggested, with Princess Beatrice standing nearby.

Ryan later joked that the pairing made perfect sense, describing it as one famous family joining another. However, it's unknown whether Harry and Kourtney ever actually met or spoke following the conversation.

Harry met Meghan shortly afterward:

The almost-romance never materialized because Harry's life changed only weeks later.

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In July 2016, the prince was introduced to Meghan Markle through a mutual friend while she was visiting London. Although the couple initially described it as a blind date, they later shared the full story in their Netflix docuseries 'Harry & Meghan.'

According to the couple, Harry first noticed Meghan after seeing a video posted on Instagram by a mutual friend. The clip showed the former Suits actress using the popular Snapchat puppy ears filter, prompting Harry to ask, "Who is that?"

Instead of searching for Harry online, Meghan asked to see his private Instagram account to get a better sense of who he was. She was impressed by his photography, environmental interests, and charitable work before agreeing to meet him.

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Their first date took place at London's 76 Dean Street while Meghan was in the city for Wimbledon. Despite Harry arriving about 30 minutes late because of traffic, the chemistry was immediate. 

The pair met again the following evening before taking a life-changing trip to Botswana just weeks later, where they spent several days camping together away from the public eye.

The whirlwind romance led to their engagement in November 2017 and their royal wedding in May 2018.

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As for Kourtney, she eventually found her own happily ever after. After ending her on-and-off relationship with Scott Disick, she began dating Blink-182 drummer Travis Barker, and the couple married in 2022.

While the royal-Kardashian crossover never happened, Ryan's story offers a fascinating glimpse into the unexpected "what if" moment that almost changed Prince Harry's romantic history forever.