THE 14 WOMEN BEFORE MEGHAN: PRINCE HARRY’S WILD DATING HISTORY — FROM PARTY GIRLS AND ARISTOCRATS TO THE TWO WOMEN MANY BELIEVED WOULD BECOME HIS ROYAL BRIDE
Long before he met Meghan Markle and stunned the world with a whirlwind royal romance, Prince Harry was known as the monarchy’s most eligible — and unpredictable — bachelor.
The flame-haired prince spent years navigating a glamorous dating life that mixed aristocratic circles, celebrity parties, and discreet royal introductions. In total, at least 14 women were romantically linked to Harry before the American actress entered the picture and changed everything.
And while many of those romances faded quietly, a few relationships came dangerously close to becoming royal history.
Perhaps the most famous of them all was Zimbabwean-born beauty Chelsy Davy, widely believed to be Harry’s first great love. The pair met as teenagers and dated on and off for nearly seven years, surviving university life, long-distance separations, and relentless media scrutiny.
Friends say Harry was “deeply devoted” to Chelsy and even considered proposing. But the intense pressure of royal life eventually proved too much.
“Chelsy loved Harry,” one royal watcher once said. “But she didn’t want the spotlight that comes with being part of the royal machine.”
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Then came another woman many insiders believed could become Harry’s wife — actress and model Cressida Bonas.
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Introduced to Harry by his cousin Princess Eugenie, Cressida quickly became a favorite among palace observers. Elegant, well-connected and comfortable in aristocratic circles, she seemed to tick every royal box.
For two years the couple appeared inseparable, attending weddings, private holidays, and royal gatherings together. Rumors of an engagement swirled constantly.
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But once again, the pressures surrounding the royal spotlight reportedly played a role in the relationship’s end.
And beyond those two serious romances, Harry’s dating history included a string of high-society names, glamorous models, and brief flings that fueled endless tabloid headlines.
Among those linked to the prince over the years were TV presenter Natalie Pinkham, singer Mollie King, and Norwegian rock singer Camilla Romestrand.
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Some relationships lasted months. Others barely made it past a few secret dates before the royal rumor mill exploded.
“Harry always had a reputation for following his heart,” one former palace insider said. “But his love life was never simple.”
Everything changed in 2016 when the prince met American actress Meghan Markle. Their romance moved at lightning speed, culminating in a fairy-tale royal wedding in 2018 that captivated millions around the world.
Today the Duke and Duchess of Sussex have stepped away from official royal duties and built a new life together abroad.
But as interest in the royal family continues to surge, Harry’s colorful romantic past remains a source of fascination — a reminder that before Meghan Markle entered the picture, the prince’s journey to love was anything but straightforward.
