Though Prince Harry and Prince William’s ongoing rift has no doubt cooled relations between the younger brother and his sister-in-law Kate Middleton, most royals fans can remember a time when the trio were extraordinarily close. Indeed, it was not so long ago that Harry referred to the Princess of Wales as “the big sister he never had.”

The duo met back when William and Kate were college sweethearts at the University of St. Andrews in the early 2000s. Harry later recalled the moment he met his brother’s future wife in his 2023 memoir Spare, noting that he “liked” her and that she could be described in three simple words: carefree, sweet, and kind.

Elsewhere in Spare, Harry mentioned that Kate had done a gap year in Florence, Italy, “and had an interest in photography, art, and clothes,” according to Hello!. To that end, the future princess helped William and Harry pick out outfits for a “fancy-dress birthday party” with a “cringy” theme: “Natives and Colonials.”

“Harry, who admitted to disliking both fancy-dress parties and themes, was particularly unenthusiastic about this one,” according to Hello!. “However, William’s new girlfriend, Kate, offered to help them find outfits.”

Harry also wrote about how he enjoyed making Kate laugh and how he connected with her “heavily disguised silly side.” And, when William and Kate (finally) tied the knot on April 29, 2011, the Duke of Sussex was reportedly “pleased that she’d forever be by William’s side and how she was a good match for his older brother,” according to Hello!.

Much has changed in the years since those 2011 nuptials, however. Following Harry and Meghan’s exit from the royal family in 2020 and the release of his aforementioned bombshell memoir Spare, it remains unclear whether or not reconciliation is in the cards for the Duke of Sussex.