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Princess Diana Reportedly Had A Crush On Ex-Prince Andrew And Sent Him Valentine's Cards, King Charles' Biographer Reveals: 'I Was Startled When I Found Out'

June 20, 2026 by Maria Pierides
shefinds | Celebrity
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Princess Diana reportedly had a teenage crush on ex-Prince Andrew, and even sent him anonymous Valentine’s Day cards years before she began dating the future King Charles, according to a newly-released royal biography.

According to Catherine Mayer’s new book, Divide & Rule, published on June 18th, Charles wasn’t the first royal to catch Diana’s eye, as she seemed to have had romantic feelings for his younger brother more than a decade earlier! Keep reading for more info…

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Princess Diana and Andrew hugging

Princess Diana Reportedly Sent Ex-Prince Andrew Anonymous Valentine's Day Cards

Mayer, who previously wrote the 2015 biography Born to Be King: Prince Charles on Planet Windsor, said the surprising revelation came from one of Diana's former school friends.

According to the friend, the mom-of-two anonymously sent Valentine's cards to the late Queen Elizabeth II's youngest son when she was around 15 or 16 years old, long before she joined one of the most famous families in the world.

At the time, the former Duke of York was considered one of Britain's most eligible young bachelors and attracted significant public attention. But even still, it's something that Mayer was quite taken aback by! "I was quite startled when I found that out," Mayer said, according to The Telegraph. "That was new news."

While Diana ultimately married Charles in 1981 and became Princess of Wales, Mayer's book offers a fascinating glimpse into her teenage years and a little-known chapter of her early interest in the royal family.

Princess Diana with Charles and Andrew

Princess Diana Found Andrew 'Aggressive And Rude' Compared To 'Sensitive And Thoughtful' Charles

This is even more surprising given what has previously been reported about Princess Diana's thoughts on her brother-in-law. According to Andrew Lownie's 2021 book, Entitled: The Rise and Fall of the House of York, Diana found Andrew's behavior frustrating and difficult to understand.

"One moment he would be diligent and polite, the next aggressive and rude," Lownie wrote. "Like his father [Prince Philip], he had a short temper, a rather Germanic sense of humor, and did not bear fools gladly."

Lownie also claimed that Diana felt Andrew's personality "wasn't for [her]." She reportedly described him as someone who was "not a doer," adding that he was "very happy to sit in front of the television all day watching cartoons and videos."

The author contrasted the two royal brothers, noting that "Charles was sensitive and thoughtful," while "Andrew was macho, confident, and extroverted, the sort of son Philip had always wanted."

Author:

Senior Celebrity Writer

Maria has spent the last decade writing about entertainment, fashion, and lifestyle for online and print publications all around the globe – including InStyle, OK!, and The Mirror. At SheFinds, Maria covers breaking celebrity news, red carpet looks, celebrity transformations, A-list couples, and has a watchful eye on celebrity social media accounts. You can reach her at contactmariapierides@gmail.com