The most awkward Royal Family moments, from overheard conversations to children out of control

Not even the Royal Family are immune from some seriously awkward gaffes

L-Princess Charlotte sticking out her tongue, R- Princess Diana falls asleep
(Image credit: Getty Images)

Has a family ever been as photographed as the Royal Family? From their iconic portraits to effortless photos capturing their best off-duty style, the Royal Family are notoriously difficult to catch off guard. 

It's difficult... but not impossible, as these photos prove. 

The most awkward Royal Family moments

"Whatever in love means"

A photo of Prince Charles and Princess Diana as they announce their engagement

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Arguably one of the most awkward moments from the royals was the then Prince Charles' toe-curling comment in front of the world's press after announcing his engagement to Princess Diana. 

Rather than being full of love and praise for his new fiancée, Charles left the room - and the world - completely bewildered with his odd choice of words. 

A journalist at the engagement announcement in 1981 told the couple, "You both look very much in love," Diana replied, "Oh, yes. Absolutely." Charles, however, chose to say, "Whatever 'in love' means." 

Cue... awkward silence. 

Prince Harry acting out

A young Prince Harry sticking his tongue out, while being held by Princess Diana

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Prince Harry has become something of a renegade royal, having quit 'The Firm' to move to California and then releasing an unprecedented tell-all memoir. 

But, as it turns out, the Prince has been making things awkward for his family from the very early days. 

During the Trooping the Colour parade in 1988, Harry took his mum, Princess Diana, by total surprise as he decided to stick his tongue out at the thousands of people coming to witness the spectacle outside Buckingham Palace.

One of the funniest examples of royal children struggling to behave at royal events

Silencing the future King

Savannah Phillips shushes Prince George

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If this was a few centuries ago, such a gesture to the future King of England could have you locked away in the Tower of London (or worse!). 

Fortunately, things have changed and rules have relaxed, otherwise this awkward moment of Savannah Phillips (Princess Anne's granddaughter from her son, Peter Phillips) shushing Prince George could have ended very differently. 

The moment might have been a bit awkward and embarrassing for the royals, as their kids were clearly misbehaving on the balcony of Buckingham Palace, but it was endearing and funny for everybody else.

The Princess of Wales dances with a mascot

Kate Middleton dancing with a Paddington Bear mascot

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Being Kate Middleton comes with plenty of perks - from access to incredible fashion and enjoying some truly dazzling tiara moments

However, as Princess of Wales, she sometimes finds herself forced to take part in some awkward social moments that she can't just say no to or avoid (like many of us would choose to do). 

One such awkward moment saw the Princess dancing with a giant Paddington Bear mascot in front of a packed train station in London. Not the most graceful moves from Catherine, but when your partner is a human-sized teddy bear, the blame lies with him.

A Princess acting most unroyal

Princess Charlotte sticks her tongue out next to Kate Middleton

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Unlike her younger brother Prince Louis - notorious for stealing the show with some mischievous antics - Princess Charlotte is usually on her best behaviour.

However, the Princess of Wales (and her mum, Carole Middleton) found themselves in an awkward situation as they rushed to stop young Charlotte from sticking out her tongue at the King’s Cup Regatta. 

Kids - even royal ones - will be kids. 

Even the Queen can be a sore loser

Queen Elizabeth at the Epsom Derby 2011

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Was it slightly awkward for Queen Elizabeth II to let her feelings known when her horse didn't win at the Epsom Derby? Sure. Was it funny to see someone as iconic as Britain's longest-reining monarch be such a sore loser? Absolutely. 

During the famous derby, Her Majesty - a lifelong lover of horses and a talented racehorse breeder - had one of her horses in the race. 

Apparently, the horse, Carlton House, had been an early favourite to win but only managed a third-place finish.

Charles and Camilla have their feathers ruffled

Charles and Camilla watch an eagle fly

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King Charles and Queen Camilla learnt the hard way that not every royal photo opportunity ends out the way they hoped. 

Back in 2015, Charles and Camilla attended the Sandringham Flower Show where they met Zephyr, a bald eagle who was the mascot of the Army Air Corps. 

Not quite anticipating the wingspan of such a powerful bird, Their Majesties were left with a photograph looking both terrified and awkward. 

Harry's goofiness caught on camera

Prince Harry jokes with Queen Camilla during Trooping the Colour 2019

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While Prince Harry's goofy side is part of the reason he's so popular - with plenty of candid photos of the Prince bringing the levity over the years - not every in-joke or private gag with your nearest and dearest translates to the wider public. 

Prince Harry proved this when he joined his brother, Prince William, and mother-in-law, Queen Camilla, for Trooping the Colour in 2009. 

He clearly was amusing his family with whatever joke he was making, but all the rest of the world sees is a most awkward photo of Harry.

Not everyone had Royal Wedding fever

Prince William and Kate Middleton kiss on the Buckingham Palace balcony

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On July 29, 1981, Princess Diana and the then Prince Charles started something that would become one of the most popular traditions among royal fans - the balcony kiss. 

Prince William and Kate Middleton's 2011 wedding carried on this iconic tradition - and the world was waiting with bated breath for it. 

Everyone, it seems, except one. Prince William’s goddaughter, Grace Van Cutsem, was caught looking unimpressed, nearly upstaging the royal couple in a hilariously awkward moment of thunder-stealing.

Charles and Diana have an awkward interview

Prince Charles and Princess Diana in Australia, 1983

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To put it mildly, there's plenty about the relationship between King Charles and his first wife, Princess Diana that was awkward for the Royal Family. 

But the warning signs of their ill-fated romance were there from the very beginning. 

As early as 1983, when Charles and Diana (accompanied by their nine-month old son, Prince William) went on a tour of Australia, they had an interview which left everyone around them feeling mightily uncomfortable. 

As Charles was giving a speech to the press, Diana couldn't help but roll her eyes behind her husband. Everyone laughed. Except Charles, who quipped, "It's amazing what ladies do when your back is turned."

Yikes. The video exists online, and Netflix's The Crown even recreated the exact moment.

Any time Princess Margaret was sassy

Princess Margaret

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Queen Elizabeth's younger sister, Princess Margaret, had that rare skill for making those around her feel awkward, without breaking a sweat herself. 

Known for a love of the finer things with a deliciously decadent morning ritual, Princess Margaret was also famous for making things a tad difficult as her team and the other royals had to contend with her penchant for having loose lips and a sassy nature. 

From insulting the Hollywood elite to some romantic scandals, you could say Princess Margaret was a queen of making things awkward for the conservative royals. 

Catherine has a Marilyn moment

Members of the Royal Family at Princess Eugenie's wedding, 2018

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Kate Middleton suffered an awkward wardrobe malfunction which most women can relate to - but she saved it from being a total embarrassment with her usual grace. 

While glammed up for Princess Eugenie's wedding in 2018, the guests collided with the gusts as they battled some heavy winds.

Queen Elizabeth nearly lost her hat, and the Princess of Wales had a real Marilyn Monroe moment as her skirt nearly blew up.

Saving any real red-faced moments, Kate managed to keep her plum Alexander McQueen gown in order.

Not everyone was impressed by the Coronation

Prince Louis yawns at the Coronation of King Charles, sat with Prince William, Kate Middleton and Princess Charlotte

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On May 6, 2023, the world watched Westminster Abbey for the Coronation of King Charles III. 

It was the first coronation of a new British sovereign in 70 years, so it was a true moment in history. However, the importance of the occasion didn't seem to land with Charles' grandson, Prince Louis. 

Little Louis was caught yawning away, in what was no doubt an embarrassing picture to explain away for his parents, Prince William and Kate Middleton.

Meghan Markle's awkward gaffe

Prince Harry and Meghan Markle

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In February 2018, Prince Harry, and his then-fiancée Meghan Markle joined forces with Prince William and Kate Middleton for their very first joint appearance together. 

They were dubbed the Fab Four by the press at the time and fans were eager to see them together at the Royal Foundation Forum in London. 

Unfortunately for Meghan, she suffered a few awkward gaffes. Not only did she wade into a hotbed political issue - sharing some comments on the #MeToo movement - she also found herself having to cover her face in embarrassment. 

A damsel in distress

Kate Middleton with her heel stuck at a St Patrick's Day parade

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Many fairy tales and Disney movies show Princesses in need of rescuing, so it was a tale as old as time when Kate Middleton found herself stuck and needing some assistance from Prince William. 

The Princess, pregnant with Prince George at the time, got stuck in grating as they took part in a St Patrick's Day parade in 2013.

While it was awkward for Catherine, it was a truly relatable and reassuring moment for people everywhere that even she can have some issues with her high heels.

The Queen doesn't have a poker face

Queen Elizabeth II

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Queen Elizabeth II was known for being the unshakeable foundation of the Royal Family for a history-making 70 years. She often set the tone for the family, ushering in a no-nonsense attitude and being a steady presence for seven decades. 

So, Her Majesty probably found it a little awkward when this hilarious expression was caught on camera during the 1997 Windsor Horse Show. 

While it wasn't too incriminating, it was refreshing to know that even the Queen could get caught out with some less-than-perfect pictures. 

The Spice Girls leave Charles and Harry blushing

Prince Charles and Prince Harry with Victoria Beckham and Mel C of the Spice Girls

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King Charles was once left red-faced when Ginger Spice (Geri Halliwell-Horner) kissed him and allegedly pinched his bum, rendering all his power and protocol useless in the wake of girl power. 

And Prince Harry also had a Spice Girls memory when he looked like a classic awkward teen surrounded by the iconic girl band as a 13-year-old on his first-ever official overseas engagement with a trip to South Africa.

Kate casts a spell

Kate Middleton at the Harry Potter Studios in London

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Catherine, Princess of Wales is no stranger to casting a spell on those she meets on her iconic royal tours or when she is in her element with young fans

However, in 2013, during a visit to the Warner Bros Studios Tour in London, Kate was caught getting a little bit too into her Harry Potter fantasies, pulling some hilariously awkward faces as she played with a replica wand.

William and Kate are seated for some unexpected jokes

Prince William and Kate Middleton

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Prince William and Kate Middleton are talked about every day of the year, and they're no doubt used to seeing some uncomfortable headlines concerning themselves or their family members. 

However, they've never been put in such an awkward position as they were in 2020, when they attended the BAFTAs ceremony.

The pair had to keep their reactions in check as Hollywood star Margot Robbie accepted an award for Brad Pitt. Reading his speech, Brad made references to Prince Harry's (at the time, very fresh) exit from royal life.

Reading his speech, Margot read, "He says that he’s going to name this Harry because he’s really excited about bringing it back to the States with him."

Princess Beatrice's hat steals the show

Princess Eugenie and Princess Beatrice and the Royal Wedding, 2011

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There were plenty of iconic facts from Prince William and Kate Middleton's 2011 wedding to earn its place in the history books, but one of William's family members nearly walked away with the spotlight - which could've been rather awkward. 

Any bride or groom knows how uncomfortable it is when someone tries to upstage your big day, but Princess Beatrice found herself the unexpected focus of the day when she arrived wearing the now infamous sculptural Philip Treacy hat. 

Some awkward dance moves

Prince William and Kate Middleton dancing in Tuvalu

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We've seen Prince William and Catherine, Princess of Wales carry out plenty of serious and impressive duties over the years, but their 2012 tour of the Far East and the South Pacific saw them do something quite unexpected - dancing. 

Wanting to honour the customs and traditions of Tuvalu, an island in the South Pacific, you can feel the awkwardness of the situation radiating from the photos. 

Anyone who has ever found themselves forced to take part in some group dancing or ice-breaking activities will surely relate. 

King Charles overheard letting his feelings known

Prince Harry, King Charles and Prince William in 2005

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King Charles grew up watching his mother, Queen Elizabeth II, rarely make her inner feelings known to the world. She was famous for being reserved in public, but was often celebrated for having a dry sense of humour and a quick wit behind closed doors. 

Charles, on the other hand, has been more animated with his feelings in the past, and one of his most awkward acts of sharing came in March 2005 during a trip to Klosters ski resort with his two sons, Prince William and Prince Harry. 

Ahead of his wedding to Camilla later that year, Charles and his sons answered questions during a press call,

However, Charles' microphone caught him stating that he "can't bear" the BBC royal correspondent, Nicholas Witchell. 

Prince William drifts off

Prince William, Kate Middleton and Prince Harry

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Falling asleep on the job? We can all agree it's about as awkward as it can get. Now add having the press watching you on top of that. 

This was Prince William's unfortunate experience in 2018 when clips caught him appearing to briefly drift off during a service at Westminster Abbey. 

However, before people get too critical of the future King, he had recently welcomed his third child, Prince Louis, to the brood. Kensington Palace was no doubt full of restless nights with two toddlers and a baby at home.

Queen Elizabeth caught doing some touch-ups

Queen Elizabeth applying lipstick

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From her fabulously colourful outfits to her flamboyant hats, Queen Elizabeth II was very rarely caught off guard when it came to her signature aesthetic. 

However, even Her Majesty needed the odd touch-up. 

In a funny, relatable moment, the Queen was caught cheekily reapplying her lipstick during an event. 

And if you were curious about what lippy Her Majesty liked, she reportedly had a few favourites. These included the Elizabeth Arden Moisturising Lipstick in the shades Pink Punch or Rose Petal.

Princess Anne falls foul of the law

Princess Anne leaves the Magistrates Court

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This one might be a step up from awkward...

Anne, the Princess Royal, holds the rather tainted record of being the only member of the Royal Family convicted of a criminal offence after pleading guilty to a charge under the Dangerous Dogs Act in 2002. 

One of Princess Anne's bull terriers bit two children while at a Windsor park. 

Donald Trump breaks etiquette (plus other hilarity)

Queen Elizabeth II and Donald Trump

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In 2018, the world watched with a mixture of curiosity and anxiety when controversial US President Donald Trump came to London to meet with the Royal Family. 

His visit inspired plenty of awkward moments. From the now Queen Camilla's wink to the press when joining the President for a dinner to Princess Anne (mistakenly) being accused of refusing to join the greeting line, things didn't run too smoothly. 

For his part, Trump broke royal etiquette as he walked in front of Queen Elizabeth II as the two inspected the Queen's Guard.

King Charles loses it over a pen

King Charles and Queen Camilla

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English author Edward Bulwer-Lytton famously proclaimed that the pen is mightier than the sword, and it was a humble pen that cut to King Charles' core during a visit to Northern Ireland in 2022. 

Charles, who to give some slack was grieving the death of his mother at the time, became agitated at a leaky pen. 

"Oh god I hate this [pen]!" the King said, standing up and handing it to Queen Camilla. I can't bear this bloody thing, what they do, every stinking time."

In one of the most subtle romantic gestures, which captures how well his wife gets him, Camilla now reportedly plans in advance.

Royal biographer Angela Levin recalls an incident where Camilla dug out a pen from her purse at a subsequent event, noting "[She] held it up to me and winked at me, and handed it to him to sign... And he sort of laughed at her and signed it."

Prince Louis does not enjoy this royal tradition

Prince Louis covers his ears at Trooping the Colour

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If Prince William and Kate Middleton were hoping to get a nice family photo for the albums from Trooping the Colour in 2022, Prince Louis slightly spoiled their plans. 

The excited young Prince did not react well to the annual flyover. 

Unfortunately for Prince Louis, this happens every year. 

Trooping the Colour has been the official birthday celebration for the monarch since roughly 1748, so he's got plenty of flypasts and parades ahead of him.

It's a Royal Knockout leaves the Royal Family bruised

L-Prince Edward, R- Sarah Ferguson and Prince Andrew

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The Royal Family might fascinate people all over the world, often the subject of documentaries and TV shows, but they seem to have a serious run of bad luck when it comes to actually starring in shows themselves. 

A 1969 BBC documentary followed the Royal Family at home in unprecedented access, however, reaction was mostly negative with some suggesting it didn't portray the family in the best light, and it has never been shown on TV again. 

In 1987, Prince Edward tried to spearhead another modernising moment for the family, getting them involved in a royal spin-off of a popular gameshow at the time, called It's a Knockout.

It saw esteemed members of the family team up with various celebrities and take part in slapstick activities. It was not well received and many considered it an embarrassing move. 

(But, to give Edward some credit, it reportedly was eventually watched by 400 million viewers worldwide and raised over £1.5 million for charities.)

Princess Diana falls asleep

Princess Diana falls asleep at the V&A museum in 1981

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Princess Diana was given a rather unwanted nickname after she was caught dozing during an event.

Dubbed Sleeping Beauty, Diana was caught dropping off during a gala performance at London's Victoria and Albert Museum.

Touchingly, the awkward moment was later revealed to be because Princess Diana was pregnant with her first child, Prince William.

King Charles caught complaining at the Coronation

King Charles and Queen Camilla in a carriage at the Coronation

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You'd think King Charles would be full of excitement - after 70 years as Prince of Wales, it was his time to take centre stage with his Coronation in 2023. 

However, His Majesty was awkwardly caught out complaining on the day. 

As clips filmed the arrival of King Charles and Queen Camilla to Westminster Abbey, footage reportedly showed them talking away with His Majesty telling his wife "this is boring."

He also reportedly added, "We can never be on time."

Prince Louis shushes his mum in front of millions

Prince Louis and Kate Middleton during the Platinum Jubilee concert

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Prince Louis isn't known for his calm demeanour at royal events, with the excited young royal always pulling funny faces and struggling to sit still. 

However, a more awkward incident took place during a special Platinum Jubilee Pageant in 2022. 

While the world watched as Queen Elizabeth commemorated her unprecedented 70 years on the throne, her great-grandson got a little feisty and even shushed his own mother. 

Tut, tut, Louis.

Jack Slater
Freelance writer

Jack Slater is not the Last Action Hero, but that's what comes up first when you Google him. Preferring a much more sedentary life, Jack gets his thrills by covering news, entertainment, celebrity, film and culture for woman&home, and other digital publications.

Having written for various print and online publications—ranging from national syndicates to niche magazines—Jack has written about nearly everything there is to write about, covering LGBTQ+ news, celebrity features, TV and film scoops, reviewing the latest theatre shows lighting up London’s West End and the most pressing of SEO based stories.