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15 Rarely Seen Photos of Prince Harry with Princess Diana

As ginger-haired Prince Harry turns another year older on September 15, these informal, rarely-seen snapshots celebrate the most magical times he spent with "the best mother ever," as he's referred to her, "who brought a breath of fresh air to everything she did."

Birth of Prince HarryJOHN SHELLEY./Shutterstock

The proud mummy holds her early gift

The world’s favorite ginger-haired prince was born Prince Henry Charles Albert David on the gray-skied Saturday afternoon of September 15, 1984, at London’s St. Mary’s Hospital. Prince “Harry”—as he’s always been called, one of the things we didn’t know about Prince Harry—arrived one week ahead of schedule after nine hours of labor, the last three of which his mum, Diana, Princess of Wales, spent reading a paperback novel. Diana was 23 at the time and is positively glowing in this snapshot, one of the first of mummy and son.

Prince Harry 1985James Gray / Daily Mail /Shutterstock

Mummy gets baby off to a “flying” start

On March 22, 1985, many years before Prince Harry would become the pilot he is, he took one of his first plane rides, accompanied by his Mum, to Aberdeen, Scotland. The plane was a Boeing 757, and Diana had picked out this adorable “flying suit” to mark the occasion. These are the most iconic photos from Harry and Meghan’s marriage (so far).

Prince Of Wales Mike Forster / Daily Mail /Shutterstock

Arriving in Majorca, on Mummy’s lap

On August 7, 1986, Princess Diana held Prince Harry on her lap as they arrived in Majorca, Spain for a holiday. Also, on the same plane flight were Prince Harry’s dad, Prince Charles, and brother, Prince William; the travel arrangements had the world in a tizzy (it broke the royal protocol of never having more than one heir to the throne on any one airplane)—just one of the rules of protocol royals are supposed to follow.

Prince And Princess Of WalesMike Forster / Daily Mail /Shutterstock

His Royal “Thumbsucker”

A year later, on another Spanish holiday in Majorca, Prince Harry is shown on his mum’s hip, his thumb firmly planted in his mouth—a seemingly unintentional reminder to the world that the prince is also a little boy just like every other little boy getting a ride in his mum’s arms. The comment that Prince Charles made after Harry’s birth broke Diana’s heart.

Prince Harry Getting An Early Introduction To Horse RidingJames Gray / Daily Mail /Shutterstock

Giddyup!

On December 31, 1987, Prince Harry got to take one of his first pony rides, with mummy Diana walking protectively beside him. One day, the prince would grow up to be an accomplished polo player. In these candid, rarely seen photos of the royal family, Prince George seems like a good candidate for being the next polo up-and-comer.

England Prince Harry William and Princess Diana, London Steve Holland/AP/Shutterstock

Cheeky monkey

What could be more adorable than a three-and-a-half-year-old sticking out his tongue at the camera? How about a three-and-a-half-year-old prince sticking out his tongue while his mum, the princess, tries to reign in his cheekiness? This is the real story of how Prince Harry and Meghan met.

Diana Princess Of Wales Prince William Prince Harry Royal Family Ski-ingMike Forster / Daily Mail /Shutterstock

Before he had ski poles

On April 16, 1991, seven-year-old Prince Harry still had not earned his ski poles (newbie skiers ski without poles until they’ve learned to properly stop and turn without using them), but something about this photo says that this adventurous little critter was trying to convince his mum to let him take the expert slope down the mountain. This is Prince Harry’s real name.

Prince Harry Education 9th Jan 1992Glenn Copus / Evening Standard /Shutterstock

Just another schoolboy and his mum

January 9, 1992, was the first day of school following Christmas break, and eight-year-old Harry hurries along with his mum toward his prep school, London’s Wetherby School Notting Hill Gate. Hope they made it on time! Learn about the ways Prince Harry and Meghan’s wedding made history.

Princess Diana and family at Thorpe Park, Britain - 1992Cassidy and Leigh/Shutterstock

Ah, the things a mum must sometimes do…

Not everyone relishes the whoosh of a log flume, but clearly, Prince Harry was in his happy place on this trip to Thorne Park in Surrey. Apparently, Princess Diana seemed to be enjoying herself as well.

Princess Diana on a skiing holiday, Lech, Austria - Mar 1994 HARTLEY/BEIRNE/Shutterstock

Oh, what fun it is to ride…

One reason losing his mum was so difficult for Prince Harry would have to be that Princess Diana was such a fun-loving and adventurous mum. Here’s a photo of Mum and son on a horse-drawn sleigh while taking a ski holiday in Austria in March 1994. This is exactly what it means to “step back” from royal duties.

BRITISH GRAND PRIX AT SILVERSTONE, BRITAIN 1994Paul Greaves/Shutterstock

Off to the races

Since 1926, the British Grand Prix has been a car-racing tradition in England. In 1994, it was held near the village of Silverstone in Northamptonshire, as it still is today. This candid shot beautifully captures Prince Harry’s impish smile and his mum, Diana’s delight at her son’s happiness.

PRINCE WILLIAMS FIRST 1ST DAYShutterstock

All dressed up, but…

It’s not that Prince Harry had nowhere to go; it’s just that this particular photo was taken on his older brother’s first day at Eton College, the distinguished prep school from which both William and Harry would graduate—get a look at these photos of Prince William with his mum, too. This photo of Prince Harry walking with his mum dates back to 1995. Prince Harry started at Eton in 1998.

PRINCE WILLIAM CONFIRMATION AT WINDSOR CASTLE, BRITAIN - 1997Shutterstock

Come this way…

In yet another instance of Prince Harry showing up for his older brother’s milestone several years before he’d take his turn, here is a photo from the 1997 confirmation of Prince William. Diana, dressed in baby blue, reaches her hand out for Prince Harry to take. It’s almost a given that the next moment, he grabbed onto mum’s hand as he entered Windsor Castle.

FRANCE PEOPLE DIANA, SAINT TROPEZ, FranceLIONEL CIRONNEAU/AP/Shutterstock

High seas adventurers

Hmmm, where might Prince Harry have gotten his adventurous spirit? Could it be his mum? Here they’re tooling around on a personal watercraft on the French Riviera, near Saint Tropez, with Diana as Harry’s faithful navigator. Sadly, this photo was snapped on July 17, 1997, not even six weeks before Princess Diana would die tragically in an automobile crash in Paris—here are some of the things we learned about her after she died.

PRINCE CHARLES, PRINCE WILLIAM AND PRINCE HARRY VIEWING FLORAL TRIBUTES AFTER DEATH OF PRINCESS DIANAShutterstock

That brave face hid his private pain

Prince Harry was devastated by the loss of his mum. Here in early September of 1997, Harry accepts a bouquet of flowers in tribute to her, the “People’s Princess,” as she’ll forever be known. A few days later, he would bravely march along in the funeral processional, his mum’s casket holding “Mummy”. Remember more of the People’s Princess with these rarely seen photos of Princess Diana.

Lauren Cahn
Lauren Cahn is a New York-based writer whose work has appeared regularly on Reader's Digest, The Huffington Post, and a variety of other publications since 2008. She covers life and style, popular culture, law, religion, health, fitness, yoga, entertaining and entertainment. Lauren is also an author of crime fiction; her first full-length manuscript, The Trust Game, was short-listed for the 2017 CLUE Award for emerging talent in the genre of suspense fiction.