Princess Diana’s Very First Royal Engagement Was a Disaster for Many Reasons

Like Meghan, Duchess of Sussex, the late Princess Diana had an exceptionally challenging time adjusting to life in the British royal family. Just 19 when she and Prince Charles became engaged and wed, the princess barely knew her future husband. Worst still, she had no idea what it meant to be a senior member of the British royal family.

As someone still coming into their own, Princess Diana found life in a fishbowl to be terrifying. She also didn’t understand the press’ obsession with her. The royals also separated her from her own family, the Spencers, which meant she had no one to truly confide in. Since she was so young, the princess often rebelled by going against the grain.

However, she did hope to make a good impression during her very first royal engagement as Prince Charles‘ fiance. Unfortunately, it was a disastrous ordeal.

Lady Diana Spencer attended her first public engagement tonight, when she joined Prince Charles at a Gala Charity Concert at the Goldsmith's Hall, London, in aid of the Royal Opera House. Princess Grace of Monaco also attends the event, as seen in other frames in this set. Note to Editors : Diana is wearing a black dress, as seen in the colour Mirrorpix pictures from this event, 22nd May 1981.
Lady Diana Spencer attended her first public engagement tonight, when she joined Prince Charles at a Gala Charity Concert at the Goldsmith’s Hall, London| Kent Gavin/Daily Mirror/Mirrorpix/Getty Images

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Princess Diana’s dress was inappropriate

Princess Diana’s very first royal engagement was a musical recital at Goldsmiths’ Hall on March 3, 1981. Unfortunately, her wardrobe choice for the evening put her on edge immediately.

The princess has chosen a bold black dress from Emmanuels. Prince Charles disapproved of it. He scolded his future bride saying that black was the color of mourning, not one to be seen on a blushing bride-to-be. The dress also proved to be a bit revealing.

In Diana: Her True Story  In Her Own Words, the late princess told royal biographer Andrew Morton that the dress was “two sizes too small.” She also explained that she “was quite big-chested then and they all got frightful excited.”

It was way more attention then the princess was hoping for on her first night out.

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Princess Diana did not know the proper royal protocol

Unfortunately prior to throwing her to the wolves, so to speak, Princess Diana was not adequately prepared with knowledge of how to deal with the press and what proper protocol was for senior royals in public settings.

The young princess desperately wanted to make a good impression. However, the pressure of it all nearly made her sick.

“It was a horrendous occasion,” she later recalled. “I didn’t know whether to go out of the door first. I didn’t know whether your handbag should be in your left or right hand. I was terrified, really ‒ at the time everything was all over the place. I remember that evening so well. I was terrified ‒ nearly sick.”

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Princess Diana was already terrified about life in the royal family

During that first outing, Princess Diana got just a taste of what was to be expected of her and it was all too overwhelming. She ended up confiding in Grace Kelly, the Princess of Monaco who was also in attendance.

“The 52-year-old Princess Grace, the object of this sort of attention back in the Fifties, notices Diana’s discomfort and suggests they retire to the ladies’ room for a little chat,” Craig Brown wrote in his book, Hello Goodbye Hello: Circle of 101 Remarkable Meetings. “Diana tells Princess Grace that she is worried her dress is unbecoming. It is, she explains, two sizes too small. Her experience tonight has suddenly made her realize how unbearable it will be to have hundreds of people always looking at her. She sees stretching ahead of her, a life without any form of privacy. What should she do? She bursts into tears. Princess Grace puts her arms around her and pats her on the shoulder. She cups her cheeks in her hands and jokes, gently: ‘Don’t worry dear. You’ll see – it’ll only get worse.’ The two women return to the throng, there to mingle and be assessed.”