Princess Diana not only struggled with her marriage to Prince Charles, but she suffered from loneliness while living at Kensington Palace. Former palace press secretary Dickie Arbiter, who worked with the late princess in the ‘80s and ‘90s, recently revealed that Diana took on some secret charitable work that was fueled, in part, “out of boredom.”
Speaking to the Daily Mail’s “Palace Confidential” podcast, Arbiter said that Diana’s friends “were reluctant to go through the security hoops” to spend time with the princess. “She had to give security her friends' names, addresses, car numbers, what time they were coming and when they were leaving,” he explained. “It was a bit of a rigmarole.”
Since Diana “was always desperate to find things to do” at night, Arbiter said that she’d drive around London seeking out people in need and giving them money.
“She would try to escape, telling her protection officer: 'I'm not going anywhere tonight. You can have the night off,’” Arbiter recalled. “Lo and behold, the car would come anyway and she'd drive around Paddington. Not just to hand money to sex workers, but to drive past and see how the homeless were coping.”
Although Diana was passionate about charity work and helping others, Arbiter said the outings were partly motivated by her loneliness. “It was something she felt she had to do, but it was also something that she was doing out of boredom,” he said.
Her interest in preventing homelessness, however, wasn't a passing whim. She served as the royal patron for multiple organizations related to the issue, including The Passage, a role now taken over by Prince William. Today, the Prince of Wales has passed his passion for helping the unhoused on to Prince George, bringing him along for a Christmas visit to The Passage in December 2025.