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Things haven’t been all that easy for Prince Harry, Duke of Sussex, since he decided to walk away from the royal family and move to California with his wife, Meghan Markle. A great number of scandals have tarnished Prince Harry and Markle’s reputation over the years, and their attempts to heal the wounds have not gone well. A trip to Australia in April 2026 was marred by photos of Meghan apparently staring daggers at the staff, not to mention their decision to cancel plans to avoid protests over their visit, according to Radar Online. Adding to all these woes are the rumors that Harry and Meghan are having money troubles.
With all the serious problems that surround him, it can be hard to remember when Harry was able to leave all his troubles behind and get a little silly. In fact, it is Prince Harry’s silliness that helped make him so popular in the first place. While the House of Windsor is known for being prim and proper with their outdated royal rules and protocols, Harry often found ways to show off a more human side of the family. Prince Harry’s tendency to break the royal rules may have made him the black sheep of the family, but it also made people feel like they could connect with him in a way that they can’t with the other royals. Fortunately, there are many photographs that capture his silly side and remind us of his better days.
Prince Harry shows off his skills with a sword
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One of the most beloved tropes in fairytales is the dashing Prince Charming who knows how to handle himself in a fight. While it has been quite a long time since any British prince has been put into a position where they need to pick up a sword and defend the honor of a fair maiden, that didn’t stop Prince Harry from showing off his form.
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Nine-Year-Old Gwen Challenges Prince Harry to a Sword Fight at the WellChild Awards. #royalfamily #princeharry#wellchildawards2025
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Seen here at the 2025 WellChild Awards, the Duke of Sussex brandishes a sword crafted with the finest yellow balloons in the land and faces off against nine-year-old Gwen Foster. Hopefully, Prince Harry was gentlemanly enough to let Foster win the day.
Prince Harry plays with a popcorn pilferer
In 2017, well before he had any children of his own, Prince Harry showed off his ability to be a goofy dad while in Canada. Here, the Duke of Sussex is seen at the Invictus Games being offered a pacifier by a young Emily Henson, whose dad was playing in the games. The video of Harry and Emily also went viral.
Emily was, for a bit, showing off her fast hands by snatching some of Prince Harry’s popcorn, but the perceptive prince soon caught on. Seeing Prince Harry goofing around with the little girl made it clear that the prince would surely be a good father to his own children one day.
Harry goes up top
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Prince Harry spent ten years in the British Army, serving two tours in Afghanistan. After leaving the military, the Duke of Sussex took an interest in helping soldiers who were injured in the line of duty, including lending his name and celebrity to the Wounded Warrior Project.
In 2015, Prince Harry joined six veterans who took part in a 1,000-mile walk to raise awareness about the difficulties faced by those who were disabled while in the military. Harry walked 17 miles with them, helping bring attention to the event, and also took some time to greet onlookers and give one British child a happy high five.
Prince Harry plays some hockey and does the dab
In 2016, Prince Harry made a trip to Aberdeen, Scotland, in support of Denis Law’s Streetsport program and ended up playing a little hockey with some of the kids. Unfortunately for the prince, it seemed like there weren’t any regulation sticks on hand, and he had to use one that was a little small. And that wasn’t all the prince did at the school.
After giving as many high-fives as he could, Prince Harry delighted the kids and teens around him by doing “the dab.” While the move is cringe-worthy today, it was still pretty popular in 2016.
Harry joins some kids for a game
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If founding the Invictus Games wasn’t proof enough that Prince Harry loves sports, his work with London’s Fed and Fit campaign should do it. In 2017, the Duke of Sussex spent a day at the StreetGames event playing games and serving lunch to some of the city’s little ones who don’t have many options for healthy meals and activities during the summer months.
While picking up a player holding the ball during a game may go against the rules, no one seemed to mind that the prince was finding new ways to score against his rival team that day. Based on the pictures, things were more silly than competitive.
Prince Harry gives a girl a twirl
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While Prince Harry and Meghan Markle’s 2026 trip to Australia may not have been as successful as they hoped, it gave one little girl the chance to live out the dream of many a child. While meeting with veteran Joel Vanderzwan outside the Sydney Opera House, Charlotte Vanderzwan took her shot and got to dance with the prince.
The Duke of Sussex lived up to his wife’s claim (per People), “He’s very good at twirling.” Harry’s twirling skills are so good that he left young Charlotte a little dizzy. After the short dance, the Duke and Duchess were presented with personalized flip-flops.
Harry found the fun in Lesotho
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In 2008, Prince Harry took a trip to Lesotho to help rebuild a school for children. Lesotho held a special place in the prince’s heart — two years earlier, he co-founded Sentebale, a charity helping children who had been impacted by the AIDS crisis, in memory of his mother, Princess Diana.
Sadly, the prince left his position at the charity in 2025, citing issues between the organization’s chairperson and the board, with Sentebale filing a defamation suit against Prince Harry in 2026. As such, this image captures a simpler time, when Prince Harry found a way to have a little fun while doing some good.
Now we know where Prince Harry got his dance moves
Prince Harry’s twirling skills may not have come naturally. In 2019, the prince stopped by the London YMCA to take a ballet lesson where he learned how to stand on one foot. As the video shows, the Duke of Sussex was a little confused by the instructions at first, but he quickly got the hang of it.
Along with picking up a new move from the ballet class, the prince took some time to hang out with a baby, who he apparently told a very good joke to. While Prince Harry’s face can’t be seen, the baby gets a good laugh from him.
Prince Harry gets his groove on in Chile
Always ready to shake what his mama gave him, Prince Harry headed to Santiago, Chile, in 2014 to visit a daycare for children with disabilities and couldn’t help but join in when the party started. In the video, Prince Harry does his best to keep up with the others as they rock out to Katy Perry’s “Firework.”
While he may not be able to match the moves of the kids, the Duke of Sussex certainly had fun letting loose for a little bit. Hopefully, he’s able to maintain his silly side no matter what happens.