Prince William Had an Awkward Dinner Party Moment with Kate Middleton and His Ex

Prince William had his fair share of relationships throughout the years (royals, they're just like us!) before he married Kate Middleton in 2011. The couple are known for their on- and off-breakups during their college days at St. Andrews University. But naturally, their not-so-secret relationship came with some drama—including an awkward encounter with one of Will's exes (opens in new tab), Carly Massy-Birch, in 2002.

In a story royal reporter and author Katie Nicholls revealed in her 2011 book, The Making of a Royal Romance that was recently resurfaced from Express (opens in new tab), Nicholls describes the time Kate and Will played a game of “never have I ever” (same) at a dinner party where Massy-Birch was also in attendance. (Will and Massy-Birch dated a little before he met Kate.)

Apparently during the dinner Massy-Birch had been one of the people who knew Will and Kate were secretly dating, but she still decided to shoot her shot: When it was her turn to play the game she said, "I’ve never dated two people in this room," knowing that William was the only one in the room that dated her and Kate, who was sitting right next to him.

William reportedly “shot a thunderous look” at Massy-Birch before whispering, “I can’t believe you just said that." It's unclear how exactly Kate reacted, but it's safe to say she probably wasn't...the happiest. Kate and Massy-Birch were reportedly friendly before the encounter, but didn't speak much after that.

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