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Prince William and Kate Middleton have been together so long that imagining either of them with anyone else is difficult. But early in their relationship, they supposedly had an unpleasant run-in with a then-recent ex of his and ended up in a cringe-worthy game of “never have I ever.”

Who is his ex-girlfriend? Plus, what did a source say she did that received “a thunderous look” from William and a permanent cold shoulder from Kate? Read on to find out.

Prince William and Kate Middleton in 2011
Prince William and Kate Middleton | Chris Jackson/Getty Images

Prince William was ‘very taken’ with his ex before things got awkward after their split, royal expert says

Carly Massy-Birch, one of William’s exes, spoke to author and royal expert Katie Nicholl about her bond with the young prince. “I’m a real country bumpkin,” she said (Cosmopolitan).I think that was why we had a connection.”

“William was in the year below, and we just happened to meet through the general St. Andrews melee. It’s such a small place that it was impossible not to bump into William, and after a while there was nothing weird about seeing him around,” she went on.

They “got on well,” she said, and added, “But I think we would have got on well even if nothing had been going on romantically. It was very much a university thing, just a regular university romance.”

According to Nicholl, a friend said William was “very taken,” but the relationship didn’t last long. And soon enough, he was courting Kate after he stole her from her ex — allegedly.

Prince William and Kate Middleton supposedly had an awkward encounter with his ex

Kate Middleton and Prince William, pictured sitting side-by-side in 2020.
Kate Middleton and Prince William | Charlotte Graham/WPA Pool/Getty Images

In the 2011 book The Making of a Royal Romance, Nicholl shared a story she heard about a dinner party that sounded like it got awkward for William and Kate. As the story goes, Massy-Birch was there, and the three all participated in a game of “never have I ever” (Express).

“When it was Carly’s turn to play she announced, ‘I’ve never dated two people in this room,’ knowing full well that William was the only one who had because Kate was sitting next to him,” recalls one attendee of the party.

Sources told Nicholl that William “shot a thunderous look” at his ex and whispered, “I can’t believe you just said that.”

According to Nicholl’s insiders, the dinner party was a way for Willam and Kate to confirm their relationship publicly. The party-goer added other attendees were left “in shock” by Massy-Birch’s remark, and Kate supposedly stopped speaking to her after that.

Prince William and Kate Middleton hit some speed bumps before they married

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The uncomfortable game wasn’t the only bump in the road William and Kate encountered before making it down the aisle. The couple briefly parted ways in 2007 after the prince supposedly had a “frank discussion” with Queen Elizabeth and now-King Charles III about feeling tied down.

But the split didn’t last long despite cold feet, and the couple tied the knot in 2011. After their engagement, they addressed their breakup publicly, chalking the brief separation up to age.