Before Prince Harry decided to settle down and marry Meghan Markle, his relationship status often made headlines. From his rumored hookup with a former Real Housewife to his on-again, off-again relationship with Chelsy Davy, Us Weekly breaks down his dating history.
“For so many people in the family, especially obviously the men, there can be a temptation or an urge to marry someone who fits the mold,” the prince explained in the first episode of Netflix’s Harry & Meghan docuseries, which debuted in December 2022. “As opposed to someone who perhaps you may be destined to be with. [It’s] the difference between making decisions with your head or your heart.”
The Duke of Sussex noted that all of his past girlfriends had their lives “turned upside down” when they started dating the famous royal.
“[I learned] the pain and suffering of women marrying into this institution. I remember thinking, ‘How can I ever find someone who’s willing and capable to be able to withstand all the baggage that comes with being with me?’” he said.
Harry met Meghan during summer 2016 after he asked a friend to introduce them when he saw the Suits star on social media.
“Meghan and I met over Instagram. I was scrolling through my feed, and someone who was a friend had this video of the two of them, it was like a Snapchat,” he recalled.
Meghan revealed she was using the puppy filter in the footage. “That was the first thing, I was like, ‘Who is that?’” Harry added.
He proposed in fall 2017 and they wed the following May.
“I remember my family first meeting her and being incredibly impressed,” Harry said on the series. “Some of them didn’t quite know what to do with themselves, so I think they were surprised, maybe surprised that the ginger could land such a beautiful woman and such an intelligent woman. But the fact that I was dating an American actress was probably what clouded their judgment more than anything else at the beginning: ‘Oh, she’s an American actress. This won’t last.’”
While their relationship has lasted — and they went on to welcome son Archie and daughter Lilibet in 2019 and 2021, respectively — Harry and Meghan opted to stop working as senior members of the royal family in 2020, relocating to California.
“By the nature of being born into this position and with everything else that comes with it and the level of hate that has been stirred up in the last three years — especially against my wife and my son — I’m generally concerned for the safety of my family,” Harry explained. “This is about duty and service I feel as though being part of this family, it is my duty to uncover this exploitation and bribery that happens within our media.”
Before Prince Harry decided to settle down and marry Meghan Markle, his relationship status often made headlines. From his rumored hookup with a former Real Housewife to his on-again, off-again relationship with Chelsy Davy, Us Weekly breaks down his dating history.
“For so many people in the family, especially obviously the men, there can be a temptation or an urge to marry someone who fits the mold,” the prince explained in the first episode of Netflix’s Harry & Meghan docuseries, which debuted in December 2022. “As opposed to someone who perhaps you may be destined to be with. [It’s] the difference between making decisions with your head or your heart.”
The Duke of Sussex noted that all of his past girlfriends had their lives “turned upside down” when they started dating the famous royal.
“[I learned] the pain and suffering of women marrying into this institution. I remember thinking, ‘How can I ever find someone who’s willing and capable to be able to withstand all the baggage that comes with being with me?’” he said.
Harry met Meghan during summer 2016 after he asked a friend to introduce them when he saw the Suits star on social media.
“Meghan and I met over Instagram. I was scrolling through my feed, and someone who was a friend had this video of the two of them, it was like a Snapchat,” he recalled.
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Meghan revealed she was using the puppy filter in the footage. “That was the first thing, I was like, ‘Who is that?’” Harry added.
He proposed in fall 2017 and they wed the following May.
“I remember my family first meeting her and being incredibly impressed,” Harry said on the series. “Some of them didn’t quite know what to do with themselves, so I think they were surprised, maybe surprised that the ginger could land such a beautiful woman and such an intelligent woman. But the fact that I was dating an American actress was probably what clouded their judgment more than anything else at the beginning: ‘Oh, she’s an American actress. This won’t last.'”
While their relationship has lasted — and they went on to welcome son Archie and daughter Lilibet in 2019 and 2021, respectively — Harry and Meghan opted to stop working as senior members of the royal family in 2020, relocating to California.
“By the nature of being born into this position and with everything else that comes with it and the level of hate that has been stirred up in the last three years — especially against my wife and my son — I’m generally concerned for the safety of my family,” Harry explained. “This is about duty and service I feel as though being part of this family, it is my duty to uncover this exploitation and bribery that happens within our media.”
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Natalie Pinkham
Harry and the British television host briefly dated in 2003 after they met four years earlier at the 1999 Rugby World Cup. They both attended the BT Sport Industry Awards in London in April 2016, but did not appear to cross paths. Pinkham was expecting her second child with now-husband Owain Walbyoff at the time.
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Cassie Sumner
Harry reportedly spent time with the model during a night out at a London nightclub in 2004. “He made eye contact as I stood at the bar with friends and he invited me to join his private table. … I thought, ‘What the hell.’ I plonked myself down next to him and it wasn’t long before he began cuddling up to me,” the model told UK’s Mirror Online in 2004. “Anyway, I can’t see myself getting invited home for tea with Prince Charles and Camilla!”
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Catherine Ommanney
Before she one of the Real Housewives of Washington D.C., Ommanney claimed she hooked up with the prince. “We had a great time and a fun evening,” she told Daily Mail’s Mail on Sunday in July 2006. “We started talking and that was it for the rest of the evening. I was quite taken aback by him!”
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Chelsy Davy
Harry and his college sweetheart dated on and off from 2004 to 2011. Davy even attended Prince William’s wedding to Kate Middleton in April 2011, but Harry and Davy called it quits shortly after the nuptials. A source told Us in January 2018 that Davy is expected to score an invite to Harry and Markle’s big day because the former couple have “remained friends long after ending their relationship.”
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Caroline Flack
The former X Factor U.K. host detailed her 2009 fling with Harry in her 2015 autobiography Storm in a C Cup. The pair were introduced by a mutual friend. “Once the story got out, that was it. We had to stop seeing each other. I was no longer Caroline Flack, TV presenter, I was Caroline Flack, Prince Harry’s bit of rough,” she wrote about the relationship.
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Astrid Harbord
Harry was rumored to briefly date Harbord, one of Duchess Kate’s friends, during a 2009 during a break from his relationship with Davy.
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Camilla Romestrand
Harry and the Norwegian singer reportedly dated for a couple months toward the end of 2010 before he once again rekindled his relationship with Davy.
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Florence Brudenell-Bruce
The prince and the lingerie model had a brief summer fling in 2011. They were first spotted together at at London’s Hard Rock Calling music festival in June, and Us reported at the time that hung out “backstage in the wee hours of [the] morning while The Killers performed live.”
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Cressida Bonas
Harry dated the model from 2012 to 2014 after they were introduced by his cousin Princess Eugenie. A source close to Bonas told Us Weekly in 2014 that their split was “very amicable.” Bonas opened up in August 2017 about how “frustrating” it is to be known as Harry’s ex. “I think it’s that thing of being pigeonholed. Especially in this country, I feel people are very quick to put you in a box or put you in a corner and think, ‘Oh, well, you’re that so you must be that,’” she said on the BBC’s Woman’s Hour radio show at the time. A source told Us in January 2018 that Bonas will likely not be invited to Harry’s wedding to Markle.
