The sweet way Princess Diana totally embarrassed Prince William on his birthday

Princess Diana’s amazing sense of humor was revealed on Prince William's birthday when she gave him a naughty birthday cake

Prince William's birthday
(Image credit: Anwar Hussein / Contributor / getty)

Princess Diana has long been known for her kindness and elegance, but she also had a cheeky sense of humor that she shared with her children, particularly on their birthdays.


On June 21, 2022, Prince William will celebrate a milestone birthday as he turns 40. After losing his mother at the age of just 15, this is one of many birthdays that the Prince has sadly spent without her. However, her naughty sense of humor when it comes to her son's birthdays will always be fondly remembered by the Royal Family, and by Prince Harry and William, who both inherited their mother’s fun side. 

Former Royal Chef, Darren McGrady, claims Princess Diana’s sense of humor was best highlighted when she chose a hilariously embarrassing cake for Prince William’s 13th birthday. 

Darren worked as a personal chef for Princess Diana and her sons for four years. It was during his time working for her at Kensington Palace that he saw the humorous way Princess Diana went about celebrating William officially becoming a teenager.

“I came into work that morning and went down to the refrigerator, opened the door and I was just confronted with the biggest pair of boobs I’ve ever seen in my life”, he previously told Hello! (opens in new tab) 

Princess Diana's former chef revealed, "The Princess had ordered a boobs cake for William’s 13th birthday."

Princess Diana

(Image credit: Princess Diana Archive / Stringer /Getty )

He went on to remark that he didn’t know anything about it and instead asked the butler about its appearance. Darren was then told that Princess Diana had ordered it for William’s birthday.

Remarking on her hilarious choice, the former Royal Chef warmly explained, "The Princess loved embarrassing people in the nicest way, in a fun way, whether it was telling a dirty, risqué joke—which usually got me. William just went bright red."

But despite the fact that then-13-year-old William was seemingly left a little embarrassed at the time, Princess Diana’s brilliant sense of humor was something she seems to have passed down to her much-adored sons.

Princess Diana

(Image credit: Tim Graham / Contributor / Getty Images)

In a move that echoed Princess Diana’s love for embarrassing people in “the nicest way’, Prince William took after his mother and joked about his brother, Prince Harry, during his wedding speech.

Speaking to PEOPLE, Claire Jones, the harpist who played at the afternoon reception at Buckingham Palace, revealed that William teased Harry, saying, “Thank goodness Claire turned up to play the harp because otherwise, we’d have to get my brother to play it instead.” 

Prince William has also made some hilarious comments while performing his royal duties. Previously he has, ‘flirted’ with an elderly woman in a sweet video from his trip to Scotland. In the video, the Prince was asked, “Can you stop flirting with residents?” Prince William laughed as he said, “Sorry I’m trying not to, I’m not sure who is flirting more!”

Prince Harry has also inherited Diana’s love of fun and practical joking, which her choice of birthday cake made clear. As reported by the Express, royal author Bryan Kozlowski claimed in his book, Long Live the Queen! 23 Rules for Living from Britain’s Longest Reigning Monarch, Prince Harry even once pranked the Queen. 

Prince Harry played a practical joke on his grandmother, Queen Elizabeth, in his youth by recording a voicemail message on the Queen's phone that said, “This is Liz! Sorry, I’m away from the throne. For a hotline to Philip, press one; for Charles, press two; for the corgis, press three.”

prince harry

(Image credit: Tim Graham / Contributor / Getty Images)

Given Princess Diana’s hilarious 13th birthday cake choice for William, it’s likely she would have appreciated the funny side of Harry’s prank voicemail. Although she is no longer with her sons to celebrate their milestones, she is still remembered by them.

So it seems that while we may miss Princess Diana’s sense of humor, her love
of fun and flair for playing practical jokes in the “nicest way” continues to shine through in her sons. 

Laura is a news writer for woman&home who primarily covers entertainment and celebrity news. Laura dabbles in lifestyle, royal, beauty, and fashion news, and loves to cover anything and everything to do with television and film. She is also passionate about feminism and equality and loves writing about gender issues and feminist literature.


Laura loves drinking and eating and can often be found trying to get reservations at London's trendiest restaurants. When she's not wining and dining, Laura can also be found travelling, baking, and hiking with her dog.