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Ex-files: Who did Harry, Meghan date before finding each other?

Chelsy Davy, Cressida Bonas, Trevor Engelson, Cory Vitiello top list

(Photo by Chris Jackson/Getty Images)
(Photo by Chris Jackson/Getty Images) (Chris Jackson/Getty Images)

Pretty soon, Prince Harry will be officially off the market. He and fiancee Meghan Markle have been pretty inseparable ever since their chance meeting on a blind date in mid-2016.

On Saturday, they'll tie the knot with the world watching.

But in case you're scratching your head, wondering who they dated previously, we've broken it down. Our list includes one former husband, a lot of ex-boyfriends and ex-girlfriends and even a few flings (we're looking at you, Harry). Some relationships were confirmed, others have just been rumored. But when it comes to the pair's dating history, we'll fill you in. Ready?

Let's start with Markle, seeing as her list is notably shorter.

Trevor Engelson

Markle met Engelson, a film producer, in 2004. The pair were engaged in 2010 and then married in September 2011. However, the love didn’t last -- and their divorce was finalized in 2013. Not much has been made public about exactly why the couple split, but it did seem amicable. The two quietly separated and dissolved their marriage in a no-fault divorce, citing irreconcilable differences. Some sources have said that the two parted ways because of Markle's role on "Suits," which kept her in Toronto, while Engelson, a New York native, stayed behind in LA. Perhaps we'll never know.

Cory Vitiello

Markle then dated celebrity chef Cory Vitiello from 2014 to 2016, according to Marie Claire Australia. He was the last man Markle was romantically linked to before meeting Prince Harry. Vitiello is from Toronto, the same city where Markle filmed “Suits.” It seems like they probably shared many a delicious meal, seeing as Vitiello is a famous Canadian chef and Markle is a self-proclaimed foodie.

Rory McIlroy

Full disclosure: Markle and McIlroy never officially confirmed their relationship. But there’s no denying that the pair were inseparable in August 2014. McIlroy, a professional golfer, has been linked to many famous women, and Markle's included on that list. The two even filmed an ice bucket challenge together. Watch the clip below.


And now for Prince Harry.

Chelsy Davy

Perhaps most notably, Prince Harry was tied to Chelsy Davy, a lawyer and the daughter of Zimbabwean safari farmer Charles Davy. The two dated on and off for seven years, from 2004 to 2011. If you think Davy looks familiar, perhaps you saw her on Harry’s arm at the royal wedding of Prince William and Kate Middleton, as she was his date. The relationship ended amicably, with many suggesting that Davy will even be in attendance at the coming nuptials this Saturday. The pair have remained friends and they don’t seem to harbor any ill will toward one another. Markle doesn't mind that they've stayed in touch either, sources have said.

Cressida Bonas

And now for a relationship that didn’t end on the best of terms: Harry’s courtship with Bonas, a model and actress. The pair dated from 2012 to 2014. Many reports suggest that Bonas couldn’t stand the public scrutiny that she endured while dating the prince. The two, introduced by Princess Eugenie, broke up only a month after Bonas attended her first official engagement with Harry.

Caroline Flack

These two were introduced by a mutual friend in 2009, but called it off rather quickly -- just as soon as word of the relationship leaked to the public, the U.K. "X Factor" host has said in interviews. Flack wrote about the brief relationship with Harry in her autobiography.

Natalie Pinkham

Prince Harry may have dated TV host Natalie Pinkham in 2003, although this is another one of those situations that was mostly rumored and not confirmed by either party directly. Still, Pinkham was often seen by Harry’s side back in 2003, and many say the two were indeed an item. Now, she is married with two children, British outlets say.

Natalie Imbruglia

When Prince Harry and Davy were on one of their "breaks" in 2009, Harry and the Australian actress and singer met through mutual friends and supposedly dated for a few months. It was never very serious, according to published reports.

Camilla Romestrand

Toward the end of 2010, Prince Harry dated the lead singer of rock group Eddie the Gun for a couple of months, but it didn’t last long. Harry eventually reunited with Davy once again, and just like that, Romestrand was out of the picture.

Catherine Ommanney

Is this story getting old yet? Ommanney -- who went on to join “The Real Housewives of D.C.” -- didn’t sound like more than a fling, at the very most. She was caught making out with Prince Harry back in 2007. It doesn’t sound like the relationship ever made it beyond that point (if you can even call it a relationship), but hey, sounds like there were sparks! So she’s still included on his list of former flames.

Florence Brudenell-Bruce

Harry and Davy split for good in 2011, which is when he launched into a relationship with Brudenell-Bruce, a lingerie model. It seemed to be more of a summer romance than anything else, and the two broke up as Harry headed out for military helicopter training.

Ellie Goulding

Goulding, who’s performed at several royal events over the years -- even William and Kate’s wedding in 2011 -- was spotted kissing Prince Harry in the spring of 2016 at a polo match. The pair were never officially an item, but they’ve definitely sparked some rumors over the years.

Lauren Pope

Pope, a model, is another one of those “was it, or wasn’t it?” cases. She and Harry were caught making out at a club in 2004. He always was a wild one, that Harry, wasn’t he?


Is there anyone we missed? Let us know in the comments.

All images: Copyright Getty

About the Author:

Michelle is the Managing Editor of Graham Media Group's Digital Content Team, which writes for all of the company's news websites.