With Prince Harry’s engagement to American actress Meghan Markle, headlines are proclaiming that the 33-year-old prince has taken “the long route to love” and that the “third time’s a romantic charm”.

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Yet has his route been particularly “long”?

He’s now engaged in his early 30s and had two prior serious relationships – plus several flings. All of which would be pretty normal if he were not a member of the royal family. (In Britain the median age of first marriage is 30 for women and 31 for men.)

Prince Harry proposed to Meghan Markle while he was roasting a chicken

However, being a prince is not a normal life. Prince Harry has been surrounded by engagement speculation for years – and has given the media plenty of women to speculate about.

As the royal matrimania revs up, let’s take a moment to revisit Harry’s bachelor days, as chronicled mainly by the United States and British tabloids.

Prince Harry’s first serious girlfriend was Chelsy Davy, whom he met in 2004 during his gap year in South Africa. (Davy is from Zimbabwe and is the daughter of a billionaire.) Davy studied law in Britain and went on to practise as a lawyer, yet the media often portrayed her as a “party girl”. Of course, Harry did his fair share of partying himself.

While they were dating, Harry’s service in the British Army and their frequent time apart were sticking points. In 2005, the Daily Mail reported that Davy gave the prince an ultimatum, saying: “It’s me or the British Army – you can’t have both.” (Harry stayed in the army, eventually doing two tours in Afghanistan.)

 

Perhaps it wasn’t just the distance that doomed Harry and Davy. Throughout their on-again, off-again relationship, there were often reports of the prince out with other women.

In 2006, Catherine Davies, who went on to be a member of the 2010 season of Real Housewives of D.C. (under the name Catherine Ommanney after a remarriage) told the Daily Mail about making out with Prince Harry after a night out in London when he was 21 and she was 34.

He kissed me, I didn’t kiss him
Catherine Ommanney on her night out with Prince Harry

“He kissed me, I didn’t kiss him. I did nothing wrong. I certainly wasn’t trying to seduce a 21-year-old,” she told the tabloid. “I was quite taken aback by him. He’s very mature.”

Pop Sugar describes this dalliance as occurring before Harry and Davy were in an “established relationship”.

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By 2007, Harry and Davy seemed to be officially together; they were spotted being affectionate at concerts and sporting events. They broke up after the prince missed Davy’s 22nd birthday to go to a rugby match in Paris, according to the Telegraph. That split, however, didn’t stick. In 2008, Davy showed up to watch Harry receive a medal for his service in Afghanistan.

Relationship: Not in one
Chelsy Davy’s Facebook post on her split with Prince Harry

In 2009, they split up again. Davy announced their break-up in typical millennial fashion, in a Facebook post declaring “Relationship: Not in one.”

While they were broken up, Harry had brief relationships with singer and actress Natalie Imbruglia and TV presenter Caroline Flack.

By the end of 2009, Harry and Davy were back together, celebrating the prince’s birthday in Botswana. In 2010, they broke up (during which Harry had a fling with Norwegian rock star Camilla Romestrand) and got back together again later that year, according to People magazine.

 

Beachwaves ☀️

A post shared by Camilla Romestrand (@eddiethegun) on Jun 26, 2017 at 9:39am PDT

After they finally broke up, the prince rebounded with lingerie model Florence Brudenell-Bruce.

Having trouble keeping this all straight? Yeah, so are we.

I found it very difficult when it was bad. I couldn’t cope. I was young, I was trying to be a normal kid and it was horrible
Chelsy Davy, after her final break-up with Prince Harry

The media scrutiny was “crazy and scary and uncomfortable”, Davy told The Times of London last year. “I found it very difficult when it was bad. I couldn’t cope. I was young, I was trying to be a normal kid and it was horrible.”

After their final break-up, Davy went back to Zimbabwe. She now runs a luxury jewellery brand called Aya, which says on its website that it sources its gemstones through “ethical mining” in Africa. Davy has remained close with Harry, and attended William and Kate’s wedding in 2011. “I think we will always be good friends,” Davy told The Times.

In 2012, the prince started dating Cressida Bonas, a wealthy descendant of King Charles II, whom Harry met through his cousin, Princess Eugenie. The couple went on a romantic ski trip to Kazakhstan and attended Bonas’ sister’s wedding together.

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However, according to The Sun, the couple split up in 2014 after Bonas was “overwhelmed by the attention she was getting while engagement rumours swirled around the young couple”. In August, Bonas told the Daily Telegraph that it was “incredibly frustrating” to be defined by her relationship with Harry; like Markle, Bonas is an actress.

After his break-up with Bonas, Harry was romantically linked to singer Ellie Goulding; the pop star sang at William and Kate’s wedding.

In 2016, Harry met actress Meghan Markle, whom he has fiercely defended against tabloid criticism.

 

She’s older than Harry, biracial, divorced and American, not the typical background for a British princess, which has brought on racist and sexist attacks. But the couple represents many of the changes in how their countries pair off: In the US, one in six newlyweds are marrying someone of a different race or ethnicity, and in Britain, one in 10 marriages is interracial.

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Speaking to the BBC, a 28-year-old French and British woman who’s in an interracial marriage said of the royal couple: “This will set a great example for England and it’s an honest representation of British society.”