Prince William Comes Face to Face with His Teenage Crush Again – Decades After Princess Diana's Cheeky Set-up

When Prince William took his seat at Buckingham Palace's grand dining hall last week, he likely didn't expect to be facing a familiar figure from his teenage years — one who had once left him red-faced and fumbling for words.

Prince William's past and present collided at Buckingham Palace on December 3, 2025, when he was reunited with Claudia Schiffer, the supermodel he once met under unforgettable — and slightly embarrassing — circumstances arranged by his late mother, Diana, Princess of Wales.

The encounter took place during a state banquet honouring German President Frank-Walter Steinmeier and First Lady Elke Büdenbender, with the prince seated opposite some of the most high-profile guests in the room.

Among them was Claudia, who attended as a guest of the German delegation. For the formal occasion, the 1990s fashion icon wore a black Balmain dress featuring gold and multicolour embellishments.

Now married to English film director Matthew Vaughn, who was knighted by King Charles III in July 2025, Claudia carries the title Lady Drummond following her husband's appointment as Lord Drummond for his services to the creative industries.

At the banquet, she was seated next to United Kingdom Prime Minister Sir Keir Starmer, and a few places down from His Majesty the King and Catherine, Princess of Wales.

Opposite them sat Queen Camilla, First Lady Büdenbender, and Prince William, who shared a particularly unique connection with the guest of honour — one that dated back more than three decades.

As a young teenager, the Prince of Wales had been surprised at Kensington Palace by none other than Claudia — along with Naomi Campbell and Christy Turlington — after Princess Diana arranged for the trio to greet him when he returned home from school.

The unexpected introduction was designed with Princess Diana's trademark mischief, but also affection — a reminder of her playful side and close bond with her eldest son.

Prince William later described how the moment left him feeling stunned and mortified in equal measure. In a past interview, he reflected on being "completely and utterly awestruck," recalling how he went red-faced and struggled to find his words upon meeting the women whose posters had decorated his bedroom walls.

"I think I pretty much fell down the stairs on the way up," he admitted, laughing at the memory. The encounter, while overwhelming for the shy schoolboy at the time, left a lasting emotional imprint. The prince would go on to describe it as a touching, if cheeky, gesture of maternal love.

Though the banquet marked the first widely publicised reunion between the Prince of Wales and Claudia in years, they have crossed paths before — most notably in 2002, when the model presented him with the Porcelanosa Cup following a charity polo match in Hampshire.

As images from the banquet surfaced online, many took to social media to share their reactions to the full-circle moment — a collision of royal nostalgia and high fashion.

Some were quick to defend Prince William's teenage awkwardness. One person said, "He was a typical teenager." Another added, "She was a grownup young woman and he was very young. No wonder he looked awkward and embarrassed. Anyway he married the best girl in the world to be our future Queen [sic]."

Others praised the warmth behind the original set-up, with one comment reading, "So cute but it looks to me that he married the most beautiful woman of any of those women! Glad they are friends. A touching gift and memory from his mother!"

Another netizen reflected on Princess Diana's possible motivations, sharing, "If I remember correctly, Diana did it to drag his teenage brain back into reality and remember that any of the supermodels or other famous women of the time, were just real people and should be treated as such[sic]."

"Just like he was human but plastered on many a teenage girls poster wall, like his mum been constantly photographed, the photos don't tell you about who that person is really like [sic]," the comment continued.

Even Catherine, Princess of Wales, seemed to enjoy the moment, according to one sharp-eyed viewer who typed, "Look at Princess Catherine's face. I think she's enjoying this."

In the end, the unexpected reunion served as a quiet nod to the past — a reminder of Princess Diana's enduring influence and the moments that continue to shape the man who will one day be king.

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