How Princess Diana totally embarrassed Prince William on his birthday

Princess Diana’s amazing sense of humor was revealed when she gifted Prince William a naughty birthday cake on his 13th birthday

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

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.

Prince William has just celebrated his 39th birthday, on 21st June 2021. 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 to 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! Online.

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

Prince William with Diana, Princess of Wales and Prince Harry on the day he joined Eton in September 1995

(Image credit: Photo by Anwar Hussein/WireImage via 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 Helping Prince William With A Jigsaw Puzzle Toy In His Playroom At Home In Kensington Palace

(Image credit: Photo by Tim Graham Photo Library via 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. Recently, he ‘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.”

Britain's Queen Elizabeth II and Prince Harry share a joke as they watch Prince Charles and his bride Camilla Duchess of Cornwall leave St George's Chapel in Windsor following their marriage blessing, 09 April 2005

(Image credit: ALASTAIR GRANT/AFP via 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, as seen by Meghan Markle’s sweet tribute to Princess Diana in new book The Bench.

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. 

Emma is a Senior Lifestyle Writer with five years experience working in digital publishing, ranging from book publishing to magazines. She currently looks after all things Lifestyle for Woman&Home, GoodToKnow and My Imperfect Life.

Before she joined Future Publishing, Emma graduated from the University of Warwick with a Bachelor of Arts degree in English and Comparative Literary Studies. After leaving education, she started out her publishing career in the world of books, working as a Publisher for an independent digital publisher specializing in back-list and debut commercial fiction novels. With a huge book list and a passion for bringing the best stories to the broadest audience possible, Emma filled her spare time with reading the latest best-sellers and catching up on hit adaptations.

In 2017 she joined TI Media as a fiction writing coordinator on Woman’s Weekly and Woman’s Weekly Fiction as part of the features team. From here, she used her love of books, working to bring short stories to our dedicated readers and began writing for the books pages of Woman, Woman’s Own and Woman&Home, as well as online features ranging from genre round-ups to travel pieces for 

After honing her skills, Emma branched out online in 2020 when Future gave her the opportunity to focus on digital-first. When she’s not writing about the next big lifestyle trend, she enjoys cooking, long walks and watching as many crime dramas as she can!