He once called her the sister he never had.

Once upon a time, Prince Harry and his sister-in-law, Kate Middleton, were besties. But with all the shifts in the royal family, the drama between Harry and his brother, Prince William, and health scares for both King Charles and Kate, insiders say that their once-close relationship is beyond repair and there’s “no sign of a bridge” to reconnect the two. Sources close to the Firm say that while Kate has been resting and recovering, Harry has been absent from her inner circle, which is a stark contrast to their previous relationship—Harry even went as far as saying that Kate was the “sister I never had, but always wanted.”

“What has kept her going are her family and friends rallying ’round. Though, sadly, the same can’t be said for her brother-in-law, who she was once close to,” royal biographer Emily Andrews shared. “Now, she’s faced with her darkest days. Where has Harry been?”

“With his new life in the U.S., high-profile TV appearances, and a scathing book to boot, it is unlikely that Harry’s shoulder will be one Kate has sought to cry on,” she finished. “But, there lies the rub. Surely, illness is one of the most powerful reasons to reunite and to put the past firmly in the history books? Instead, the wedge appears to be even larger, with no sign of a bridge to connect the pair.”

Royal fans know that Harry and Middleton have been growing apart since his wedding, when there was apparently a conflict over Princess Charlotte’s flower girl dress that left Meghan Markle in tears. In his memoir, Spare, Harry explained that the situation involved a text argument and Kate sent flowers and apologized after.

Following the Princess of Wales’s cancer announcement, Harry and Meghan quickly released a joint statement and wished her a quick recovery.

“We wish health and healing for Kate and the family, and hope they are able to do so privately and in peace,” it read. Kate has been out of the spotlight since the news broke, but she did make an appearance at this year’s Trooping the Colour. The royal family noted that she’ll return to her usual schedule when her medical team says she’s ready.