On September 8, Prince Harry attended a reception ahead of the 2025 WellChild Awards, where he serves as patron of the U.K. charity supporting seriously ill children.

During the event, the Duke of Sussex, 40, shared a lighthearted exchange with award recipient Declan Bitmead, 17.

When Harry asked Declan about his family, the teen mentioned having a younger brother. “Does he drive you mad?” Harry asked, before hearing that the two actually get along. With a laugh, the Duke responded, “You know what, siblings.”

After learning that Declan and his brother attend the same school, Harry added, “That sometimes makes it more challenging.”

A Glimpse Back at Harry’s Own School Days

Harry’s comments drew parallels to his own experiences, which he detailed in his 2023 memoir Spare. Reflecting on his time at Eton College, where Prince William was already enrolled when Harry arrived in 1998, he recalled, “Willy had told me to pretend I didn’t know him. For the last two years, he explained, Eton had been his sanctuary. No kid brother tagging along, pestering him with questions, pushing up on his social circle. He was forging his own life, and he wasn’t willing to give that up.”

Harry continued, “None of which was all that new. Willy always hated it when anyone made the mistake of thinking of us as a package deal… And now, to attend the same school was pure murder.”

The Longstanding Rift with Prince William

Despite the humor in his WellChild exchange, tensions between Harry and his brother remain. The once-close bond between King Charles’ sons has fractured over the years, most visibly since 2020 when Harry and Meghan Markle stepped back from their royal duties.

“Things were said that sparked the initial rift, and it’s never healed,” royal biographer Andrew Morton told PEOPLE recently.

On the same day Harry attended the WellChild Awards in London—coinciding with the third anniversary of Queen Elizabeth’s passing—he privately visited her burial site at Windsor Castle.

Meanwhile, Prince William, 43, and Kate Middleton marked the day with an appearance at The National Federation of Women’s Institute in Sunningdale, just eight miles away. Despite the proximity, there were no expectations of a reunion.

Subtle Remarks About Family

Over the summer, William himself made a comment that some royal watchers interpreted as a quiet nod to the strained relationship with Harry. While visiting the Army Air Corps in Wattisham, Suffolk, he asked soldiers, “Is the pace of life good at the moment?”

When one man replied that it was “a mixed bag,” William quipped, “Families okay? See you enough? Some of them might not want to see you that much. It’s a mixed bag sometimes.”