Meghan Markle's Hottest Boyfriends: How The Duchess Used To Choose Her Men

Meghan Markle is now happily married to Prince Harry, and they are about to have their first child together. But before dating and tying the knot with the British royal, the former American actress had a record of hookups and relationships that are quite interesting. 

Today, we'll give you a comprehensive dating list with all the Duchess' ex-boyfriends, plus some fascinating details about them, rumors, pictures together, and everything you need to know about the mother-to-be's love live. Final warning: try hard to contain your envy as these dudes are hot! Without further ado, let's get started! 


Simon Rex Cutright, also renowned as Dirt Nasty, is a comedian, rapper, model, and actor from the USA. You might remember him merely as Dirt Nasty; the alter ego he came up with to rap and tell jokes. His professional acting career is more notable, though.

He starred as Jeff Campbell in 'What I Like About You' during the first season. He was also George Logan in 'Scary Movie' 3 and 4, according to Ranker. As a model, the Californian boy has appeared on ads for Versace, Calvin Klein, and Levi’s. But you won't believe your eyes when reading what he used to do in the past.

Rex was also a porn star when he was around 18, and his first three movies were aimed at the gay market. In fact, Daily Mail claimed that Simon even won an award for Best Gay Solo Video back in 1997. The former adult films actor dated Markle in October 2004. 

However, things did not go beyond the first date. As the source reported, Simon claimed that Meg dumped him over his garlic breath after they snogged. "I'm blaming it on the garlic noodles. To this day that’s like an ongoing joke — don’t order the ­garlic noodles that ruined my chances," said the actor.

The 44-year-old rapper also speculated that his past as a porn star might have scared the Duchess off. He said it was possible that she discovered his previous job after the first outing together. "There's so many questions I don’t know the answer to about why we never went on a second date," he claimed. 


By now, most people know that the royal wedding in May was not the first time Markle walked down the aisle. She was previously married to a film and TV producer. The lucky gentleman? Trevor Engelson. According to Insider, some of the New Yorker's productions are the FX series 'Snowfall' and 'License to Wed,' a movie starring Mandy Moore.

The source also explained that the producer and the actress met in 2004, dating for six years before tying the knot in September 2011 at a brief ceremony in Ocho Rios, Jamaica. Nevertheless, their marriage was very short since they parted ways in August 2013. Town & Country revealed that the couple cited irreconcilable differences.

The union terminated in a no-fault divorce; however, the real reason for the split is still a mystery. But it seems that Trevor has already moved on with his life. He got engaged only two weeks after the royal wedding and wedded nutritionist Tracey Kurland in October last year, by Harper's Bazaar


Rumor has it that the 'Suits' actress hooked up with the Canadian hunk in April 2013. But if you were paying attention, you might have already notice that this means she was still married to Engelson. There are also gossips claiming that the Duchess' split with her hubby was because of him.

Apparently, Markle developed a very close friendship with the then 22-year-old ice hockey defenceman of the Philadelphia Flyers. And the thing is that the dates matched perfectly! However, The Sun reported the actress' spokesman denying the rumors.

"In fact, she was never alone with him, and Mr. Del Zotto had absolutely nothing to do with the end of her marriage," stated her spokesman. But when the very Trevor was asked about the NHL player, he claimed, "‘Who? Oh, him. I don’t have anything to say." Quite fishy, right?


It seems that the Duchess was into athletes as she dated another professional jock. In August 2014, it was McIlroy's turn, a Northern Irish golfer. According to Ranker, he is a member of both the PGA and the European tours, being a four-time major PGA champion and the world number one for 95 weeks in the Official World Golf Ranking.

As per Insider's report, the couple was spotted together on a few occasions, but rumors were fueled when the Irish golfer challenged Meg to complete the ice bucket challenge. There's even a video on the Internet with Roy dumping the bucket over her head in the Big Apple. 


In 2014, the Canadian hunk caught Markle's eyes, and we totally understand why. The professional chef and restaurateur, apart from being sexy, is the co-owner of The Harbord Room, a restaurant in Toronto that the Duchess of Sussex frequently visited while filming 'Suits.'

Daily Mail reported that the lovebirds maintained a secretive romance from the summer of 2014 until April 2016. People in their circle believed that the intense relationship would lead them to the altar. Actually, Insider stated that Vitiello stayed with the former actress at her place and that she spent Christmas with his family in 2015. 

Read more: Queen Elizabeth is not happy about Meghan Markle modernizing royal tradition.

However, the couple called it quits after two years, with Cory leaving the door open for Prince Harry. The cause of the split is still uncertain, but we're so glad they parted ways because Meghan met Harry just weeks later. Can you imagine what would have happened if she hadn't been single? 


Well, the British royal needs no introduction, but the story of these lovebirds has an enchanting start. In October 2016, there was a buzz that the American actress and Diana's young son were dating secretly. According to Town & Country, the two became acquainted on a blind date that a mutual friend set up in July 2016. 

Read more: It turns out that Meghan and Harry might not have custody of their first child.

Things moved quickly from there. Prince Harry invited her for a second date and then for a trip to Africa. In October, after four months of private dates, news leaked, and the whole world went crazy with the romance. However, haters didn't waste time to try to ruin the romance with racist attacks towards Meghan and her Afro-American mother.

The lovebirds also experienced the difficulties of having a long-distance relationship. But despite all odds, Harry and Meghan made it to the altar in May last year. The rest is just history. The Duke and Duchess of Sussex are now eagerly waiting for the arrival of their firstborn

Wow! Did you know that the Duchess of Sussex had such an interesting love history? Tell us your favorite guy in the comment section down below, but don't go too far because we have more exciting articles about her just for you! See you soon! 

Source: Daily MailTown & CountryInsiderDaily MailTown & CountryRankerHarper's BazaarThe Sun


  1. Buckingham Palace Gives an Official Update on Prince Harry and Meghan Markle's Baby.

  2. Eugenie and Harry’s Wedding Photos Have One ‘Sad’ Difference That Says A Lot About The Royal Family.

  3. Princess Diana Would Have Turned 57 This Year And Would Look Like This Today, Experts Say.

  4. Prince Charles Was Crying Before His Wedding Day And Prince Harry May Not Be Charles’ Son.

  5. How Kate Middleton Treats Her Children Due To Their Royal Status.

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