1. When He Politely Played the Piano
In 1985, Princess Diana participated in this photo shoot alongside Prince William and Prince Harry. I love this photo because it perfectly illustrates the personalities of both boys right off the bat. Prince William, who is always expected to deliver to the crowd, is on point. He’s smiling, he’s playing, he’s happy to be there!
Prince Harry, who has fewer societal expectations on him from the get-go, is a little more skeptical. “Why are we playing this piano? Who is it for? Why is that guy taking photos of us? Just what is going on here, anyway?”
2. When He Wore *That* Cute Little White Hat
I know that as a baby, Prince Harry wasn’t really picking his outfits, but this moment is included because Meghan Markle and Prince Harry repeated the hat choice several years later, when they took Archie to South Africa. Baby Prince Harry looked adorable in his little pom-pom-topped hat, and so did baby Archie.
3. When He Was 'That Kid' in the Family Photo
Anyone who has signed up their family for a family photo session knows exactly what this moment is like: You’re all finally sitting down, even the dog is finally behaving, and all you have to do is get one shot that will be decent enough to send out … but one of your kids just can’t help himself and has to squirm. It’s just always the way.
4. His First Steps!!!
I know that many babies all over the world take their first steps all the time and it’s just so cute, but Prince Harry’s first steps were immortalized for all the world to look at over and over again whenever we want to, and the moment is clearly adorable. Look at his determined face! Look at Prince William helping him out! Boys, you need to work out your present-day issues. What would your mother say?
5. That Time He Stuck Out His Tongue at Buckingham Palace
If you ask most Prince Harry fans what one of his cutest moments ever was, they’re probably going to at least mention this particular photo. It looks like Harry even surprised Princess Diana with this one! He chose to stick out his tongue while the family observed Trooping the Colour, an annual celebration that also marks the Queen’s birthday. Even William looks amused!
6. His First Day of School With His Big Brother
On September 11, 1989, a very delighted Prince Harry joined his big brother, Prince William, at Wetherby School for the first time. Their mother joined them as they walked to the school to celebrate their first day together. In photos from the day, Harry looks really excited to be at the school.
7. When He Stuck Out His Tongue (Again)
As many a parent knows, once children get attention (positive or negative) for a behavior, they tend to repeat that behavior. At some point, Harry probably learned that if he stuck out his tongue, he’d get a reaction, and he definitely deployed the behavior in full force as he and his family returned home after visiting Sarah Ferguson and Princess Beatrice in the hospital following Beatrice’s birth.
8. When He Couldn't Keep His Shoes On
If there’s one thing the royal family really sticks to, it’s the idea that decorum and presentation are everything. So it’s pretty sweet that an 11-year-old Harry found it nearly impossible to keep his shoes on while sitting next to his mother at an event. Given the upheaval his home life was going through at the time, the shoes were probably the least of anyone’s concerns.
9. When He Was Clearly Driving William Crazy
There have to be parts of having a younger sibling that are just flat-out universal no matter who you are. And one of those universal truths is definitely that a younger sibling will totally drive you crazy whenever they can. In this photo, I’m, like, 90% sure William is physically recoiling while Harry yells at the top of his lungs, and Diana is just like, “Just get through it.”
10. When He Spent Another Trooping the Colour Acting Out
As a mom, something that I have often admired about Diana is that she let her kids do things that bent the rules, even when she was a star on one of the world’s largest stages. I can’t imagine Kate Middleton, who seems to be a fairly rules-heavy mom (which I respect) letting Prince George or Princess Charlotte climb all over the balcony during Trooping the Colour. I love that Diana let Harry act his age as much as she could in the context of their truly unique lives.
11. When He Publicly Held His Mom's Hand
In another aww moment that really illustrates the bond that Harry and Diana had, he reached for her hand while the family walked William to his first day of school at Eton. Harry was about two months out from this 11th birthday when this photo was taken, and it’s really touching that he still wanted to be that close to his mom.
12. When He Just Totally Missed That Last Step
Like many 2-year-olds, Prince Harry probably struggled with plenty of things. One of those definitely seems to be descending the stairs off a plane. He clearly just totally missed the bottom step, but luckily his mom was on hand to perform the lifesaving half-carry, half-drag that so many of us know so well.
13. When He and Charles Were in South Africa
Much has been written about Prince Harry’s close relationship with his mom, and for good reason: It seems like it was pretty legendary. But Prince Harry is also close with his dad, Prince Charles, and the two have plenty of cute photos of themselves as well. Two months after Diana’s death, Charles and Harry visited South Africa together. It’s pretty sweet to think about now, as the two probably did a lot of bonding. It’s also a nice precursor to the visit that Prince Harry made with his own wife and son years later, and it’s possibly even one reason he’s so fond of the country in the first place.
14. When He Leaned in for a Hug From Charles
Another story that sometimes circulates is that Prince Charles isn’t very affectionate. But there are numerous photos of him with his children and his grandchildren where he’s obviously a very doting dad and grandfather. In this one, Prince Harry leaned in for a hug while at the Hurtwood Park Polo Club in 1999.
15. When He Got To Really Be a Kid
Prince Harry visited the theme park Thorpe Park with his family in April 1992, and it looks like he definitely had a blast. And in the end, all of my favorite Prince Harry moments are the ones like this, where he’s a little bit more carefree than usual, and he’s just living in the moment. Growing up royal definitely has its privileges, but the weight of that kind of life could take a toll on kids. It’s great knowing that Prince Harry and his brother Prince William have had opportunities that allowed them to see how a lot of other people live.