Prince Harry's Relationship Timeline: His Road From Bachelor to Meghan Markle

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Meghan Markle and Prince Harry at Women's Empowerment reception
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Prince Harry was once the wild child of the royal family. While his older brother, Prince William, quickly found a steady relationship with Kate Middleton, Harry took a more meandering path to finding lasting love -- which he has done with Meghan Markle, whom he weds on May 19.

The 33-year-old royal’s romances often ended up in the British tabloids, whether it was a short-lived fling, a long-term thing or just rampant speculation. The pressure of that constant public attention was a factor in the demise of more than one of his relationships.

And then along came Meghan. "I'd never watched Suits, I'd never heard of Meghan before, and I was beautifully surprised when I walked into that room and saw her [for the first time]," Harry recalled. "I was like, 'Wow, OK. I'm going to have to up my game here.'" The two kept their relationship under wraps for the first six months, taking the time to get to know each other away from the public eye.

Now that the wedding date is set, let’s take a look back at a few of the famous ladies Harry was linked to before Meghan “literally fell” into his life.

1. Natalie Pinkham

Although never officially confirmed, rumors swirled in 2003 around sports television presenter Natalie Pinkham and the status of her relationship with the then-19-year-old royal. The two denied those rumors and have since remained good friends. Natalie popped back up in tabloids in 2006, when photo negatives showing Harry groping her breast were taken from her private collection. Today, she is an accomplished media personality and is married to television executive Owain Walbyoff; the couple has two children.

2. Chelsy Davy

Chelsy Davy and Prince Harry attend Prince Harry's Pilot Course Graduation at the Army Aviation Centre on May 7, 2010 in Middle Wallop, England.
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The daughter of a wealthy Zimbabwean landowner, Chelsy became Harry's first official girlfriend after crossing paths with him in South Africa in 2004. The pair were an on-and-off couple for several years, with their every reported split making tabloid headlines in the U.K. Chelsy, then a law student, attended a few important family occasions, including Harry's Army pilot graduation in 2010. The next year, she accompanied Harry to William and Kate's wedding, sparking marriage rumors of their own, but the two split for good soon after.

3. Caroline Flack 

Caroline Flack attends 'The Prince's Trust' and TKMaxx with Homesense Awards at London Palladium on March 6, 2018 in London, England.
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During a 2009 break with Chelsy, Harry hooked up with former British X-Factor judge Caroline Flack. The 38-year-old television presenter referred to her short relationship with the prince in her autobiography Storm in a C Cup, saying that once their romance went public, it had to quickly end. "We had to stop seeing each other," she wrote. "I was no longer Caroline Flack, TV presenter, I was Caroline Flack, Prince Harry's bit of rough."

4. Florence Brudenell-Bruce

Tabloid reports linked Harry to another blonde -- Florence "Flee" Brudenell-Bruce, a lingerie model and descendant of the Earl of Cardigan -- in 2011. Their relationship was short-lived, however, as the Telegraph reported the budding Apache pilot ended things to concentrate on his Army career. She is now married to a duke's grandson, with whom she has a 3-year-old daughter.

5. Cressida Bonas

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Wedding bells once more seemed possible when Harry began dating Cressida Bonas, a British actress and model, after the two were introduced by Harry's cousin Princess Eugenie. At first, Bonas, who is five years younger than Harry, was hesitant to marry. She reportedly later warmed up to the idea, with a friend telling London's The Telegraph newspaper in 2013 that a wedding was likely to take place "next year." The pair split the following year, citing the pressures of public scrutiny as a factor.

6. Meghan Markle

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After reportedly being introduced by mutual pal Violet von Westenholz, Harry and Meghan's romance quickly took off. As rumors began to swirl around the couple, Harry took the unusual step of issuing a royal statement, effectively telling the haters to back off. Soon, several overseas vacations and public appearances together followed, with Meghan making a public declaration of love on the cover of Vanity Fair. Of course, Meghan had to meet the Queen, which she did in October 2017. By November, Meghan was moving to the U.K., and shortly after that came the official engagement.

In their first interview together, Harry and Meghan gave details of the proposal, which took place at Nottingham Cottage -- the Kensington Palace house where Harry's mother, Princess Diana, lived out her final years.

The romantic occasion came during the preparation of a home-cooked roast chicken (like all the best proposals): "It just was an amazing surprise," the 36-year-old UN women's advocate recalled. "It was so sweet and natural and very romantic. He got on one knee."

"She didn't even let me finish [proposing]," Harry added. "And then there was hugs and I had the ring on my finger. I was like, 'Can I give you the ring?' She was like, 'Oh, yes, the ring!' So, it was a really nice moment. It was just the two of us, and I think I might have actually captured her by surprise."

Speaking of the ring, the prince designed it himself, incorporating diamonds from his mother's personal collection and from Botswana, the country where he and Meghan first vacationed together.

Harry and Meghan will say their "I dos" in front of around 600 guests on Saturday, May 19, at St. George's Chapel in Windsor, England. Find out everything else you need to know ahead of the nuptials in the links below.

Meghan Markle and Prince Harry's Royal Wedding: The Complete Guide

Prince Harry Asks Prince William to Be His Best Man When He Marries Meghan Markle

Meghan Markle’s Biggest Film and TV Roles, From ‘Suits’ to '90210' and Hallmark Movies