Comedian Reveals Prince Harry Almost Dated a Kardashian Before Meeting Meghan Markle: 'She Was...'

Prince Harry and Meghan Markle hit things off on their very first date itself in 2016. The couple, who married 2 years later, have two children and are going strong despite their turbulent royal exit. Although Markle appears to be Harry’s first American girlfriend, things could have been very different. Comedian Katherine Ryan recently revealed that she once tried to set Harry up with a Kardashian sister.

Ryan revealed that she tried to set Harry up with Kourtney Kardashian when they both attended a party at Jimmy Carr’s London home in 2016. Recounting the events of the night, Ryan told the Daily Mail, “As soon as I went in, I saw Kourtney Kardashian there with Princess Beatrice. I went straight over to her because I knew this woman, because I’m so invested in the family and the reality show.” She added, "I said, 'You need to leave Scott.' I was right. And she said, 'Well, how can I do that? He’s in my house right now.' And I said, 'Don’t go back to the house – you need to leave Scott.'"

Ryan was alluding to Kourtney's on-again, off-again relationship with Scott Disick, the father of her three children. She further recalled, “She was, like, 'Well, I don’t know, who would I even be with?' And I was, like, 'Prince Harry, maybe?' This was pre-Meghan.” The comedian continued, “I said Prince Harry because she was in the UK...two royal families uniting.” At the time, Harry was single after his failed relationships with Chelsy Davy and Cressida Bonas. As per the Daily Mail, he once said in a TV interview, “‘I’m not so much searching for someone to fulfil the role, but obviously, you know, finding someone who would be willing to take it on.”

Harry and Kourtney never ended up going on a date, and he met his match in Markle the same year. Interestingly, today, the Sussexes are reportedly pretty chummy with the Kardashian family. She Knows reports that Harry has been seen regularly chilling with Kris Jenner’s boyfriend, Corey Gamble. Meanwhile, Markle’s mother, Doria Ragland, was photographed in 2024 smiling beside Jenner and Kim Kardashian. As reported by The Mirror, a source dished, “It’s no coincidence that the Kardashians all move in the same circles as Meghan’s new circle. It’s just a slam dunk for the two families to team up, but Kris doesn’t want to push too aggressively, too soon.”

The Duchess of Sussex is also allegedly quite fond of Harry’s near-girlfriend. An insider told InTouch Weekly, “Meghan really admires what Kourtney has done with Poosh, she reads it all the time and loves how unapologetic the whole concept is.” The source added, “In a lot of ways, she and Kourtney are similar, they’re both these granola types that are super devoted moms.” Kourtney also resides near Montecito, close to the Sussexes' lavish mansion in the area.