A Timeline of Meghan Markle’s Dating History


Meghan Markle has lived the dream of countless girls all over the world. Like something out of a fairy tale, she met a handsome prince, became an actual princess and then managed to live happily ever after (well, moreso after they escaped the Royal Family).

In fact, Meghan and Prince Harry are in the news so often that you might think he is the only love she has ever known. In reality, the romantic timeline for Meghan Markle is about as complicated as it gets!

Meghan had some real romantic highs and lows before meeting Harry. And she even had a previous husband, which caused more than a few scandals after Harry proposed to her. 

Want to know more? We’ve got all the juicy details of Meghan Markle’s dating history! 

2004–2013: Trevor Engelson

When you read or hear “Meghan Markle’s husband,” the first person you think of is Prince Harry. However, Meghan actually had a husband long before she met Harry.

Meghan dated American movie producer Trevor Engelson from 2004 to 2010. They made for a natural match: he specialized in helping to launch Hollywood careers, and Markle was an aspiring actor at the time.

Things got more serious in 2010 when the couple got engaged. One year later, they had a Jamaican wedding ceremony that combined the natural beauty of the area with the vibe of a raucous party.

Sadly, their union wasn’t made to last. The two divorced in 2013. Meghan has kept her thoughts on their former marriage mostly to herself, but Engelson believes they broke up due to her starring in the show Suits. While that show made Markle a household name, it also kept her shooting in Toronto, Canada, far away from her Los Angeles home she shared with Engelson.

How well did Engelson take the split? Well, Deadline reports that as of 2017, he is trying to create a TV divorce comedy about a man sharing custody with his ex-wife after she marries a British prince!

Summer 2014: Rory McIlroy

Aside from Prince Harry himself, Trevor Engelson was the major romance of Markle’s life. But after they split, she still found time to date other men. Though whether or not she actually dated Rory McIlroy is a subject of some debate.

McIlroy is a famous pro-golfer whose athletic outings have taken him all over the world. Like many famous world travelers, he has a string of beautiful women that he may or may not have been romantically involved with.

And Meghan Markle is one of them. The two were spotted on a date in the summer of 2014, and they looked awfully cozy with one another. Later, though, those close to each party say they enjoyed hanging out and just being friends.

While things seemed very casual with Mcllroy, Meghan Markle was surprisingly serious with the next romance in her life.

2014–2016: Cory Vitiello

In 2014, Meghan Markle began dating Cory Vitiello. If you don’t already know, Vitiello is a very successful chef based out of Canada. In addition to making regular appearances on television, Vitiello owns several Toronto restaurants that locals absolutely love.

But did Meghan Markle love what Vitiello was bringing to the table? Even though they dated for two years (from 2014-2016), those close to the couple thought it was pretty casual. For example, one insider familiar with both Markle and Vitiello told The Daily Mail, “They were a very handsome pair and well suited, but you got the impression it was a sometimes superficial relationship.”

The insider also thinks that the couple was more focused on their careers than their relationship. “Cory was always very focused on his job and his work. In that respect, they both put their careers first. The relationship came second.”

Nonetheless, these two might have dated a bit longer. However, Meghan soon ran into Prince Harry, and things really took off from there.

2016–Present: Prince Harry

Harry and Meghan have their own personal “meet cute” story. A friend who knew both of them set them up on a blind date back in 2016. Meghan immediately wanted to plan their next date. And as Town and Country Magazine reports, Harry knew Meghan was “the one” from “the very first we met.”

Harry’s actions certainly matched his thoughts. After their second date, he invited her on a trip to Africa with him. They dated for several months, and Meghan was meeting the Royal Family by the end of 2016.

While the press dragged Meghan’s name through the mud, the Queen herself approved of Meghan. They took another trip to Africa, a trip to Norway, and even made long-distance love work while Meghan filmed Suits.

The two got engaged in November 2017. Their wedding the following May was a stunning and star-studded affair, despite controversies and complications from Meghan’s father. Since then, the two have started a family and even left royal responsibilities behind to start a new life in America.

Now, Meghan is pregnant with her second child. And away from the pressures of both the Royal Family and the British press, her “happily ever after” can truly begin.

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