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Prince Harry was once very close with Prince William’s wife, Kate Middleton. The two could often be spotted sharing a laugh at an event, and despite Harry being a “third wheel” Kate quickly took Harry under her wing once she married William.

Prince William had a lengthy courtship with Kate, whom he dated for almost a decade before the two finally wed. And Harry once revealed that he “never” thought William was actually going to marry the now-Princess of Wales.

Prince William, Kate Middleton, and Prince Harry in casual wear
Prince William, Kate Middleton, and Prince Harry in 2012 | Mark Cuthbert/UK Press/Getty Images

Prince William and Kate Middleton dated for almost 10 years

William and Kate had a bit of a tumultuous love story to the point where the press had nicknamed her “Waity Katie” because William was dragging his feet so much on proposing. William and Kate met at Univeristy of St. Andrews as freshman back in 2001, and by 2002, the two had started secretly dating. They briefly split in 2004 before rekindling the relationship shortly after, and the royal went public with his leading lady in 2005 when Kate joined the family on their ski trip.

Fast forward to 2007, and William dumped Kate once more because he wasn’t done sowing his wild oats. Of course, she drew him back in, and he finally proposed in 2010 — almost a decade after meeting his future princess.

Prince William walks with Kate Middleton in 2008
Prince William and Kate Middleton in 2008 | Tim Graham//Getty Images

Prince Harry thought Prince William would ‘never’ marry Kate Middleton

Prince Harry, who is several years younger than William, had an instant friendship with Kate. He loved her for William and gave an adoring speech about the couple on their wedding day. However, Harry once said he thought William would “never” end up with Kate.

“We all thought that it was never going to happen for him,” Harry said after the couple’s engagement, according to Cosmopolitan. “I think he’s done the right thing. He’s waited, and he’s done it when he feels right, and it’s a huge step,” Harry continued, seemingly referring to William taking his time to propose.

“She’s a fantastic girl,” he continued. “I’m really looking forward to getting her under my wing—or she’ll be taking me under her wing probably.” Of course, things shifted drastically just five years later, when Harry met Meghan Markle.

Kate Middleton stands in a car between a waving Prince William and Prince Harry
Prince William, Kate Middleton, and Prince Harry in 2016 | Jeff Spicer/Getty Images
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Prince Harry no longer has a good relationship with Prince William and Kate Middleton 

Though Harry and Kate were quite close before Meghan entered his life, things have since shifted, and Harry no longer has a good relationship with his brother and sister-in-law. When Harry started dating Meghan Markle in 2016, it supposedly caused tension between him and William because William thought Harry was moving too quickly — Harry married Meghan after knowing her for less than two years.

Today, Harry resides in California with Meghan and hardly ever speaks to William and Kate. Harry and William had a major falling out, and Harry certainly aired plenty of dirty laundry about his childhood with William in his memoir, Spare. Still, Harry plans to attend his father’s coronation on May 6, so it’s unclear if there is another chance for the brothers to work things out.