Royals Inside Prince Philip's Rocky Relationship with Princess Diana — and Their Personal Letters The royal "outsiders" were initially close but gradually drifted apart as Diana's relationship with Prince Charles collapsed By Phil Boucher Phil Boucher Phil Boucher is an editor at PEOPLE and based in London. People Editorial Guidelines Updated on November 11, 2022 01:34 PM Share Tweet Pin Email Prince Philip had a unique yet rocky bond with Princess Diana. Having married into the royal family in 1947, Philip — who died on April 9, 2021, at age 99 — could understand the difficulties of being an "outsider" in the world's most famous family. He was also "initially charmed" by the beautiful, fun-loving princess as she struggled to adapt to her new position in life. Listen below to the episode of our daily podcast PEOPLE Every Day for coverage from the wake of Prince Philip's passing. "When (Diana) found the restrictions of royal life difficult, it was Philip who helped her," writes royal author Ingrid Seward in her new book Prince Philip Revealed, excerpted in the first issue of PEOPLE Royals. "Once she was married, she never sat next to her husband; she was always sat next to Philip at the endless black-tie dinners, and he took care of her. "Diana found the Balmoral dinners a massive strain and the atmosphere stifling," Seward continues. "When the piper came around the table after dinner with his kilt swirling and his pipes whining, she couldn't wait to leave the room." Princess Diana and Prince Philip. Eric BOUVET/Gamma-Rapho via Getty This bond continued after the publication of Andrew Morton's tell-all 1992 book Diana: Her True Story, which revealed the full extent of Diana's struggles during the collapse of her marriage to Prince Charles (now King Charles III, after the September 2022 death of Queen Elizabeth II). After the book's publication, the Queen and Philip arranged a family meeting with Charles and Diana in their private sitting room at Windsor Castle — a moment captured in season 4 of the hit Netflix drama, The Crown. During the conversation, Philip asked Charles and Diana to "try to think of their children, the monarchy and the country instead of their personal woes," says Seward. Away from view, the Duke of Edinburgh also privately adopted a much gentler approach and started writing letters to Diana in the hope that he could subtly influence her. Prince Philip at the 1981 royal wedding of Charles and Diana. "He tried to make her face facts and deal with the problems within her marriage, explaining he knew first-hand the difficulties of marrying into the royal family," says Seward. Philip signed the letters "Pa," and initially sympathized with Diana's plight, even going so far as to say that Charles "was silly to risk everything with Camilla." "We never dreamed that he might feel like leaving you for her. I cannot imagine anyone in their right mind leaving you for Camilla," he added in one of the notes. "Such a prospect never entered our heads." In another letter, Philip offered to do everything he could to save their marriage. "If invited, I will always do my utmost to help you and Charles to the best of my ability. But I am quite ready to concede that I have no talent as a marriage counselor," he wrote. Prince Philip and Princess Diana on the Buckingham Palace balcony. Terry Fincher/Princess Diana Archive/Getty Sadly, the letters failed to heal the enormous rift in Diana's marriage. Over time the bond between the two royal outsiders also crumbled as steadily as Diana's relationship with Prince Charles — partly because Philip told the princess she was wrong to have her extra-marital affairs. "(Philip) realized that Diana's behavior was having a detrimental effect on the institute of the monarchy," Seward adds in Prince Philip Revealed. Get the premiere issue of PEOPLE Royals for glamorous new photos and inside stories royals fans haven't seen or read elsewhere. Subscribe at peopleroyals.com/launch Diana, meanwhile, "came to dislike Prince Philip as she found him impossible to deal with," Seward continues. "He might be entertaining as a dinner guest" (Diana) explained, "but as a father-in-law he was too judgmental." Despite this, Diana did at least appreciate the motive behind Philip's letters as her marriage floundered in 1992. Eleven of the "outsiders" notes were revealed during the 2007/2008 inquest into the tragic deaths of Diana and Dodi Fayed in August 1997. Philip, Diana and Charles on the Buckingham Palace balcony. "Dearest Pa, I was particularly touched by your most recent letter, which proved to me, if I did not already know it, that you really do care," Diana wrote in reply to Philip's "marriage counselor" letter. "You are very modest about your marriage guidance skills, and I disagree with you!" Another said, "I was so pleased to receive your letter, and particularly so to read that you are desperately anxious to help." Diana also said that she appreciated her father-in-law's "great understanding and tact" — not qualities Philip was exactly famous for during his near-century-long life. Tellingly, the princess signed off all her letters to the Duke with endearments such as "with my fondest love." A.G. Carrick/Diana Memorial Fund/Getty Can't get enough of PEOPLE's Royals coverage? Sign up for our free Royals newsletter to get the latest updates on Kate Middleton, Meghan Markle and more! Yet even the secret correspondence could not survive the devastation of Diana's collapsed marriage. The inquest heard that by 1994 and 1995, Philip's letters to Diana were of a very different tone. Her friend, alternative therapist Simone Simmons, told the 2007/2008 inquiry that Diana showed her "two letters that really upset her." Lawyer Michael Mansfield then asked Simmons if the letters were "extremely derogatory" about Diana? "Yes and very cruel as well," Simmons replied, adding that they left Diana "red in the face."