The now 40-year-old royal was single at the time and struggling to find someone willing to embrace the unique challenges of royal life. 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 Harry and Kourtney Nearly Crossed Paths
Katherine recalled attending a 2016 party at comedian Jimmy Carr’s home, where she encountered an unexpected pairing: Princess Beatrice and Kourtney Kardashian.
“I walked in and saw Kourtney Kardashian with Princess Beatrice,” Katherine said. “I went straight over to her because I knew exactly who she was — I’m so invested in the Kardashians and their reality show.”
At the time, Kourtney was still navigating an on-again, off-again relationship with Scott Disick, the father of her three children. Katherine remembered advising her: “You need to leave Scott.” Kourtney replied, “How can I? He’s in my house right now.” Katherine urged her: “Don’t go back to the house. You need to leave him.”
A Bold Matchmaking Idea
During their conversation, Kourtney asked who she could possibly date instead. Katherine didn’t hesitate: “Prince Harry, maybe?”
To her, the idea made perfect sense — two famous families, both accustomed to intense public scrutiny, potentially coming together in an unexpected romance.
At the time, Harry had been open about the difficulties of finding a partner. In a rare interview, he explained, “I’m not so much searching for someone to fulfill 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
It’s unclear whether Katherine ever seriously pursued her matchmaking idea. There’s no evidence that Harry and Kourtney ever met or communicated.
Later that same year, Harry would meet Meghan Markle, then best known for her role in Suits. In his memoir Spare, Harry revealed that he first noticed Meghan after seeing her photo on Instagram. While he and Meghan have often said they met on a “blind date,” Harry admitted he had admired her online first.
Their introduction is widely attributed to Violet von Westenholz, a friend of Harry’s who worked in PR for Ralph Lauren, although some reports credit fashion designer Misha Nonoo.
