Once in his life, Prince Harry made Kate Middleton cry in front of Prince William. That particular moment went down during Prince William and Kate’s royal wedding, where Prince Harry was the best man. It happened roughly nine years ago but remains one of the most touching royal wedding moments to this day.

As Prince William’s only brother, Prince Harry had a huge role to play in his brother’s wedding. In fact, he was hands-on with most of the preparations to make sure that the day would be a remarkable one for his elder brother, his wife-to-be and their reception guests.

Although the royal wedding was filled with light moments for those in attendance, one particular moment made Kate shed a tear during the event. In his best man’s speech during the wedding reception held at Buckingham Palace, Prince Harry turned the tables when he talked about the good qualities of his brother and how his romance with longtime girlfriend Kate had been an inspiration to him.

In the 2013 book “Kate: A Biography,” royal author Marcia Moody revealed that while Kate managed to hold it together all day, she broke down in tears during Prince Harry’s speech. Prince Harry inserted bits of humor in his message, but the sincerity of it all touched Kate to the core.

“I’ve got to know Kate pretty well but, now that she’s becoming part of the family, I’m really looking forward to getting her under my wing — or she’ll be taking me under her wing probably,” Prince Harry said. “She’s a fantastic girl. She really is. My brother’s very lucky, and she’s very lucky to have my brother. I think the two of them are a perfect match,” he added.

Prince Harry also said that their late mother, Princess Diana, would have been so proud and happy for them. This left both Kate and Prince William teary-eyed.

The Duke of Sussex went on with his classic sense of humor, telling the guests that Prince William did not have a “romantic bone in his body” before he met Kate. The moment Prince William started cooing down the phone with the girl, he said, he knew that what Prince William and Kate had at the time was already serious. He even mimicked his brother, William, calling Kate “Babykins,” drawing laughter from the crowd.

Prince William married Kate on April 29, 2011. Their wedding was one of the most watched royal weddings in history, with an estimated 23 million simultaneous viewers around the world.

Prince William, Prince Harry, Meghan Markle and Kate Middleton Prince William, Duke of Cambridge; Catherine, Duchess of Cambridge; Prince Harry, Duke of Sussex; and Meghan, Duchess of Sussex, attend a service marking the centenary of WW1 armistice. Paul Grover- WPA Pool/Getty Images