Kourtney Kardashian Was Nearly Set Up With Prince Harry

Before Prince Harry found his princess in Meghan Markle, an unexpected royal pairing almost came to fruition. Reports indicate that in 2016, Canadian comedian Katherine Ryan considered playing matchmaker, attempting to connect the British royal with American reality television star Kourtney Kardashian at a party in London.

The potential setup unfolded during an event hosted by British-Irish comedian Jimmy Carr. Ryan, a self-professed avid follower of the Kardashian family's reality show, observed Kourtney Kardashian in conversation with Prince Harry's cousin, Princess Beatrice. Seizing the moment, Ryan approached Kardashian, who at the time was navigating an on-again, off-again relationship with Scott Disick, the father of her three children: Mason, Penelope, and Reign.

During their conversation, Ryan offered Kardashian unsolicited dating advice, directly telling her, "You need to leave Scott." Kardashian reportedly responded, "How can I? He's in my house right now." Ryan pressed the point, advising, "Don't go back to the house. You need to leave him." When Kardashian then asked Ryan for a suggestion on who she should date instead, the comedian pointed to Prince Harry. Ryan explained her rationale, stating, "I said Prince Harry because she was in the UK - two royal families uniting," referencing the Kardashian family's status as "reality TV royalty." She further noted the practical aspect, "She was right there in the UK. It seemed obvious."

Kourtney Kardashian, born Kourtney Mary Kardashian in Los Angeles, California, rose to widespread fame in 2007 with the debut of "Keeping Up with the Kardashians." The reality series offered an intimate look into the lives of her family, including her mother Kris Jenner and attorney father Robert Kardashian. Beyond the show, she co-owned the D-A-S-H clothing boutiques with her sisters and later launched her lifestyle brand, Poosh, in 2019, followed by a health brand, Lemme, in 2022. Her personal life, particularly her relationship with Scott Disick, was a frequent storyline on the show.

Prince Harry, the Duke of Sussex, has been a prominent figure in the British royal family. Prior to his highly publicized courtship with American actress Meghan Markle, which began in 2016 and led to their marriage in May 2018, Harry had several high-profile relationships. His past partners included Chelsy Davy, whom he dated intermittently from 2004 to 2011, and Cressida Bonas, with whom he was in a relationship between 2012 and 2014. Public reports indicated that both Davy and Bonas found the intense public scrutiny associated with a royal relationship challenging. In an interview years before 2016, Prince Harry had spoken about the difficulties of finding a partner willing to embrace the demands of royal life, stating, "I'm not so much searching for someone to fulfil the role, but finding someone who would be willing to take it on."

Katherine Ryan, the Canadian comedian behind the proposed matchmaking, has established herself as a notable figure in British entertainment. Having moved to the United Kingdom in her early twenties after studying city planning, Ryan gained significant popularity through appearances on British panel shows such as "Mock the Week" and "8 Out of 10 Cats." She later achieved international recognition with Netflix stand-up specials like "Katherine Ryan: Glitter Room" and "Katherine Ryan: In Trouble," known for her sharp wit and observational comedy often drawn from personal experiences and pop culture.

Although the introduction between Kourtney Kardashian and Prince Harry never formally took place, the revelation of this near-setup has generated considerable public fascination. The story prompts speculation about a "what if" scenario, inviting imagination into how different Prince Harry's life might have been had the connection progressed. Some discussions have even drawn parallels between the Kardashian family and the British royal family, noting their respective positions as prominent public dynasties in their own rights.

The anecdote also provides additional context to Prince Harry's dating life before he met Meghan Markle. Her own entry into the royal family as an American actress sparked significant global interest, and the timing of Ryan's suggestion in 2016 is notable, occurring just months before Harry began dating Markle. Kourtney Kardashian, for her part, later married musician Travis Barker in May 2022. Recent reports have also indirectly linked this story to ongoing discussions about Prince Harry's comfort with Meghan Markle's increasing involvement in Hollywood culture, suggesting a potential contrast in lifestyles had he pursued a relationship with a reality TV star.

This amusing historical footnote serves as a reminder of the unexpected intersections that can occur in the worlds of celebrity and royalty, and how quickly paths can diverge or align. The tale of the almost-setup continues to intrigue, offering a glimpse into a different potential chapter for two very public figures.