The Untold Story of Prince Harry’s Almost-Royal Hollywood Romance

Before Meghan Markle entered the picture, Prince Harry’s love life could’ve taken a very different turn — one that almost led him to another Hollywood star. Long before royal weddings and Netflix deals, whispers of unexpected celebrity match-ups surrounded the young prince. And according to comedian Katherine Ryan, there was a moment when Harry might have ended up with another woman.

Real life or royal life?

But while Megan may be venturing into the world of reality TV, it seems like she’s not the only reality TV star that caught the prince’s eye.

The woman who once had Harry smitten.

According to surprising new reports, Harry was almost set up with someone who lives far outside the world of crowns and castles — someone who ruled a different kind of kingdom: Kourtney Kardashian.

So when Kourtney Kardashian asked comedian Katherine Ryan who she should be dating instead, Ryan didn’t miss a beat. “Prince Harry, maybe?” she replied.

At the time, Harry was still single and had recently opened up in a rare interview about the difficulties of finding love as a royal. Speaking to CBS in 2012, he said, “I’m 27 years old, and not so much searching for someone to fulfill the role, but obviously, you know, finding someone that would be willing to take it on.”

Ryan later revealed that she once tried to set up the prince with a Kardashian sister—Kourtney, specifically. Interestingly, Kourtney was dating Scott Disick during that time, but Ryan still floated the royal match idea. Whether the two ever connected remains unclear, but we do know what happened next: later that same year, Prince Harry met Meghan Markle—and the rest is history.

Destiny had other plans.

While the two never met, this serves as a reminder of how different choices or circumstances could have led to entirely different paths.​

In the same year, Katherine Ryan suggested Harry may be a great match for Kourtney, the prince met Meghan Markle. Their connection was immediate, leading to a relationship that would eventually challenge royal norms and captivate the world. Together, they have navigated the complexities of public life, stepping back from royal duties and forging their own path.​

Their journey hasn’t been without challenges, but their partnership has remained a focal point of their endeavors, from charitable work to media projects.​

Kourtney Kardashian, of course, has found her own happy ending. Now married to Blink-182 drummer Travis Barker, the couple shares a child together and are raising their blended family with love.