Do Prince William & James Middleton Get Along? Inside Their Relationship

What must it feel like for your sister to bring home her new boyfriend, only for him to be the future king of England? Catherine, Princess of Wales' siblings Pippa and James Middleton understand that rare feeling. And, in his memoir "Meet Ella: The Dog Who Saved My Life," James was impressively honest about how he didn't initially go easy on William, Prince of Wales. "I remember putting him through his paces when we first met," James wrote. "Did he deserve my sister? He had to earn my trust." The future princess's younger brother softened to William in part because he seemed to really like James' dog Ella, and James has been open about how his beloved pets have helped his mental health.

During a 2024 chat with Us Weekly, the businessman delved into his own sense of protectiveness, opining, "Even though I'm the little squirt of their brother — probably getting in the way — [I] still had to make sure that he had my approval." Likewise, in his memoir, he wrote about admiring Prince William and Kate Middleton's relationship from afar. As for the author's personal bond with his brother-in-law, James shared, "When it comes to those sorts of bits of advice and having been brought up in a female dominant household, and very much with strong capable women surrounding me, I've enjoyed having sort [of] this older brother type figure to bounce other questions."

Prince William notably stepped up for the entire Middleton family after his relationship with Kate Middleton initially went public. James Middleton acknowledged in a September 2024 interview with The Sunday Times how jarring it was when the paparazzi swooped in on their otherwise normal clan. "William was a fantastic support for us as a family," James confirmed. "He did everything he could to protect us from the intense interest, not just in Catherine, but also her immediate family. But at that time I was already in a vulnerable state of mind and it was an added pressure."

However, James also disclosed in "Meet Ella" that William was intimidated by a Middleton family tradition and seemed to not be terribly fond of playing card games with them. Detailing what would typically happen when James and his family played a game called Racing Demon, the author recalled, "William flinches at our ruthless determination to win at all costs." James continued, "He's delighted to be the first out, and when no longer compelled to take part, he slinks off to cuddle Ella." 

In fact, the Prince of Wales would sometimes try to take his leave before they even started playing the game by offering to walk her. "My sisters and I exchange a knowing glance: William, for all the competitive rigour of his military training, is happy to be a loser at cards," James wrote. For more Middleton family drama, check out the awkward way James' wife Alizée Thevenet met William and Kate.