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Princess Diana was one of the most recognizable faces in the world for decades before her death. Throughout her marriage, she was closely guarded, but on occasion, the People’s Princess shook off her bodyguards and headed out solo. It wasn’t to grab a drink unaccompanied, hit up a nightclub, or even take in a movie. The princess left the confines of the palace to meet regular people and lend a helping hand, all while driving herself.

Princess Diana drove solo through Paddington to hand out money

Dickie Arbiter, Buckingham Palace’s former press secretary, opened up about Diana’s secret outings on the Daily Mail’s Palace Confidential podcast in October. According to Arbiter, Diana would drive around London’s Paddington neighborhood, giving money to sex workers and checking on people experiencing homelessness to “see how the homeless were coping.”

Arbiter was candid about her motivations. “It was something she felt she had to do, but it was also something that she was doing out of boredom,” he said. Diana reportedly found royal life mundane, stifling, and, more than anything, lonely. Her impromptu outings helped her feel connected.

She didn’t just take to the streets

Princess Diana’s after-hours outings took her to some of the area’s poorer streets, but she also stopped in at hospitals. Sharon Smith, a manager at London’s Mildmay Mission Hospital, told People in 2017 that the princess would call ahead to arrange private visits with patients. “She’d ring up and say, ‘I’ll be along this evening, no cameras, it’s a private visit,’” Smith recalled.

That hands-on approach became part of Diana’s legacy. In 1987, she was famously photographed shaking hands with an HIV patient without gloves, a gesture that helped challenge stigma at the height of the AIDS crisis. Diana herself described wanting to understand the suffering of others. In a 1991 letter, she called her work with the sick a “self-development programme” that gave her “a deep understanding of those who suffer.”

Diana never really acclimated to royal life

Those close to Diana have long linked her outreach to her own isolation. Just two days after her July 1981 wedding to then-Prince Charles, she wrote to a Buckingham Palace footman, Mark Simpson, that his company made her stay easier because “it was so terribly lonely.” A decade later, she wrote to her friend Dudley Poplak, “I do feel extremely isolated more than ever now.”

Her loneliness only grew as her already cold marriage unraveled completely. Despite being surrounded by security almost constantly, she didn’t feel safe. Allegedly, Diana felt watched rather than protected. In December 1993, a year after her separation from Charles, she gave up her full-time police protection. She reportedly feared her officers were passing information about her private life to the royal family. She only accepted police protection when she was out with her sons.

Her former protection officer, Ken Wharfe, has said he believes that decision left her vulnerable and may have contributed to her death. In 1997, Diana was killed in a car crash in Paris while relying on private security. Lord Paul Condon, who led London’s Metropolitan Police at the time, later told the inquest into her death that he believed she would have survived had she accepted police protection.