Before Prince Harry was happily married to Meghan Markle and a dad to two beautiful children, he was often the third wheel hanging out with older brother Prince William and his wife, Kate Middleton. It’s not like he didn’t date — he enjoyed the on-again, off-again company of Chelsy Davy for many years and had a serious relationship with Cressida Bonas, but no one as special as Markle.
But if we look back on his dating history, there were rumored relationships (maybe a fling or two), but no one rocked his world the way his wife has. Harry certainly enjoyed his single years (and some of the stories were wild), but when he was ready to settle down, he knew Markle was the one “the very first time [they] met,” according to Harry at their engagement photo call, via Harper’s Bazaar. But it’s fun to take a look back at who was in the Duke of Sussex’s life before Markle — and it’s nice to see he is still friends with some of his exes, a few who even attended his wedding.
Take a look at the photos and see how many faces you remember — a few might have only been rumors — but he definitely had a thing for blonde singers and actresses back in the day.
Natalie Pinkham (2003)
Natalie Pinkham and Prince Harry go way back to another century — 1999 — when they first met at the Rugby World Cup, per US Weekly. It took a few years, but the sports reporter went on to date the royal in 2003. Their paths have crossed a few times over the years with her work and his charitable efforts and they reported remain friends to this day.
Cassie Sumner (2003)
Well, the palace is happy this one-night stand doing going any further. A 19-year-old Harry met model Cassie Sumner at a nightclub during his younger, wilder days. They reportedly enjoyed an evening of canoodling, which Sumner happily blabbed about in an interview.
She joined him at his private table and that’s when the hijinks ensued. “It wasn’t long before he began cuddling up to me. He seemed fascinated with my breasts, because he spent more time looking at them than my face,’ she revealed to the Daily Mail. “At one point I could feel his hands running up and down my thighs, and I gave him a playful slap. I began giggling so he snuggled up close and starting whispering in my ear, telling me how sexy I looked.He asked repeatedly: “Is there somewhere we can go?” I said “Don’t be silly” – but it only seemed to encourage Harry more.”
And it’s no surprise this entire fling ended before it even began. The royal family probably still sweats about this moment.
Chelsy Davy (2004-2011)
Harry’s sweet, young relationship with Chelsy Davy was covered heavily in the press. They broke up as many times as they got back together, but the royal family welcomed her with open arms each time.
She was even Harry’s +1 to Prince William and Kate Middleton’s wedding in 2011, so that’s kind of a big deal. But she didn’t think the royal life was for her because of the media attention and she knew the relationship had to end. “It was so full-on: crazy and scary and uncomfortable,” she told The Times. “I found it very difficult when it was bad. I couldn’t cope.”
Astrid Harbord (2009)
This romance could have been really interesting had it held up because Astrid Harbord was a good friend of sister-in-law Kate Middleton. The duo was seen clubbing it up one night in London and a brief romance occurred while he and Chelsy Davy were taking a break (again).
Harbord stayed good friends with Harry beyond their fling and eventually became his PR representative. That partnership eventually ended after Harry became serious with Meghan and they changed their household communications structure.
Caroline Flack (2009)
TV presenter Caroline Flack was thrilled to meet Prince Harry through a mutual friend. They enjoyed each other’s company for some time in 2009, but once the press started to catch on about them dating — they had to call the whole thing off. “I was no longer Caroline Flack, TV presenter,” she chronicled in her memoir, Storm in a C Cup, via the Daily Mail. “I was Caroline Flack, Prince Harry’s bit of rough.”
Mollie King (2010)
The Saturdays singer Mollie King spent a lot of time denying she ever dated Harry, telling the Evening Standard, “No, I’m not going out with him – I’m serious. Everyone wants to believe it because he’s royalty. Everyone would like it to be true but it’s not. He’s very out of my league, come on.”
Well, the truth is she did date the royal and eventually fessed up to their relationship two years later to Closer magazine, via Digital Spy. “Yes, I have met Harry, and we did go out for a drink.”
Camilla Romestrand (2010)
Prince Harry and singer Camilla Romestrand might have something along the lines of friends with benefits because she seemed to be the only one doing the talking about their relationship. She’s confided to a few people about her friendship with Harry,” a source told the now-defunct News of the World, via CBS News.”She talks about staying overnight at ‘the Palace.’ She says he was a ‘total gentleman’ but doesn’t divulge much else.”
The Eddie The Gun front woman and the royal eventually went their separate ways as she continued to focus on her music career.
Florence Brudenell-Bruce (2011)
Once Prince Harry and Chelsy Davy had broken up for good, he had a summer fling with model Florence Brudenell-Bruce. The romance didn’t last too long because there were apparently trust issues early on. “She felt he had a wandering eye all the time and she wasn’t really into not knowing who he was flirting with or talking to when they were apart,” an insider told the Daily Mail.
Cressida Bonas (2012-2014)
Actress Cressida Bonas was Harry’s last serious relationship before he met Meghan. And the reported reason for their split is rather heartbreaking because the two really were in love.
Royal author Katie Nicholl claims that Bonas was “‘completely spooked’ while watching TV coverage of William, Kate and George touring New Zealand and Australia that spring,” according to an excerpt from her book Harry: Life, Loss, and Love, via The Sun. “There was no way she wanted that sort of attention and she told Harry so.” Harry was “left heartbroken” over the situation.
In Harry’s tell-all memoir Spare, the royal talked about how meaningful his relationship with Bonas really was. According to an excerpt obtained by the New York Post, it was with Bonas that Harry cried for the first time talking about his mother since burying her. Though the conversation left Harry feeling “indebted” to his then-girlfriend, they broke up not long after. Harry explained she did not want “to take on the stresses that came with being part of royalty.”
Ellie Goulding (2015)
Did Prince Harry date pop star Ellie Goulding? Their possible coupling was the source of much speculation in 2015 after the Daily Mail reported that they were seen “chatting, flirting and eventually kissing” at a post-polo event. Of course, no photos were allowed at the party, so it’s only hearsay from a source.
What we do know is that the duo’s friendship extends back to his 30th birthday, where she performed. She also was a part of the closing ceremonies at the 2014 Invictus Games, the charity that is close to Harry’s heart. And even if they had a flirtation, Harry met Meghan a year later and the rest is history.
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