Prince Harry Once Caused Princess Diana ‘Embarrassment’ by Repeating Her ‘Risqué Joke’ to a Teacher, Author Says

It’s common for children to occasionally embarrass their parents, and it seems Princess Diana once experienced this with her younger son, Prince Harry. According to people who knew her, Diana loved to joke around, but Harry once repeated an adult joke she said to a teacher.

Princess Diana wearing a white outfit and sitting next to young Prince Harry, who is wearing a suit
Princess Diana and Prince Harry in 1995 | Tim Graham Photo Library via Getty Images

Princess Diana and Prince Harry are known for their mischievous personalities

Diana had allegedly acknowledged that Harry took after her more than Prince William did. According to her former chef, Darren McGrady, the late princess used to say, “William is deep like his dad and stubborn, and Harry is a hothead like me; he does the first thing that comes into his head.”

Both Diana and Harry were known to have rebellious streaks. For example, Diana did not easily conform to the rigid rules of royal life. She often broke dress codes and openly disagreed with the royals’ traditional way of raising their kids. When Harry was a young adult, he also had an image as a “bad boy” prince who frequented nightclubs and got into fights with photographers.

Prince Harry once caused his mother ‘embarrassment’ by repeating her ‘risqué joke’

According to author Robert Jobson, Harry’s similarity to Diana sometimes did cause her “embarrassment.”

“On the school run one morning, she started telling a risqué joke, apparently unconcerned that Harry was drinking in every salacious word,” Jobson wrote in the book William at 40: The Making of a Modern Monarch (via Daily Mail). “Her police protection officer — aware that the language was inappropriate for young ears — tried to stop her mid-flow, but she was having none of it.”

Jobson continued, “On arrival at Wetherby School in West London, William ran off to his classroom, while Harry immediately started telling the new joke to the headmistress. Belatedly, Diana — who’d gone red with embarrassment — managed to stop him reaching the punchline.”

Princess Diana did not often discipline her kids

Although there is no doubt that Diana loved her children and was a hands-on parent, sources have shared that she allegedly did not discipline them. 

Jobson wrote that the princess found Harry’s mischiefs “hilarious” and even “actively encouraged” them.

“She adored her sons and was always hugging and kissing them — but care of the boys, when they were home from school, was often left to the staff,” Jobson wrote. “Fully aware that her younger son was especially wilful and stubborn, Diana also tended to leave discipline to his nannies and protection officers.”

Jobson detailed one story of a Scotland Yard officer giving young Harry a driving lesson in Prince Charles’ Rover Discovery. When the lesson was over, Harry allegedly refused to accept it and “stamped his foot down hard on the accelerator.”

“The car slammed into a stone wall, though, fortunately, no one was hurt,” the writer said. “As one of his protection team observed, Harry could be like ‘a little Rottweiler’ when he didn’t want to stop doing something.”

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