Meghan Markle Ex-Files: The Duchess' Surprising Romantic Past Exposed!

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Earlier this year, Prince Harry married Meghan Markle before the eyes of the world at Windsor Castle in his native England.

In many ways, it was like you'd expect from royal wedding - loaded with pageantry, tradition, and a whole lot of stuffiness.

But if you've followed their relationship before, during or since the wedding, we certainly don't need to remind you of this:

Meghan Markle is not the typical royal bride.

She is older than Harry (37 to his 34) an American, a former actress; and (perhaps most controversially) a divorcee.

In fact, unlike some of her more prim and proper predecessors, fair Meghan has a rather extensive romantic history.

Take a look below at the men who wooed the Duchess of Sussex before she became a British historical figure ...

1. Young Meg

Young Meg
Before hitting it big (relatively speaking) on U.S. basic cable drama Suits, Meg was just another young woman taking whatever work she could find in the wild west of modern day Hollywood. Like most up-and-coming model/actresses, she often found herself in some unusual positions.

2. What's the Deal?

What's the Deal?
For a time, Meg was one of the "Briefcase Girls" on the popular game show Deal Or No Deal. This involved looking hot and holding a briefcase. Hey, it paid the bills ... and it wasn't long before Markle was able to parlay this and rise through the ranks to become a legitimate actress.

3. Suit Up

Suit Up
Before her relationship with Harry, Meghan was most familiar to a small but loyal number Americans as one of the stars of the critically-acclaimed USA Network legal drama Suits.

4. Always a Go-Getter

Always a Go-Getter
She certainly didn't waste any time in carving out a career for herself. And it seems Meghan applied that same level of ambition to her love life.

5. Rule-Follower

Sources say Markle was a strict adherent of the controversal women's dating guide entitled The Rules. What does that mean exactly?

6. Meghan's Men

Meghan's Men
“Meghan used to quote The Rules all the time and really put it into practice with a number of her boyfriends," says one insider. And those boyfriends were a motley crew, indeed ...

7. The Argentinian Businessman

The Argentinian Businessman
Meg's first serious boyfriend as an adult was a South American business tycoon, whom she dated during her first year of college at Northwestern.

8. The Good Life

The Good Life
“He was a successful businessman and it was a case of, ‘I will send a car for you, be ready,'" says the source. "She was really taken by that.”

9. Simon Rex

Simon Rex
Not long after embarking on a career in Hollywood, Meghan briefly dated the actor and rapper Simon Rex. Can't believe she let him get away, right??

10. Scary Movies

Scary Movies
Perhaps best known for his role in the Scary Movie films, Rex also performs in the hip-hop crew Three Loco, alongside Riff Raff and Andy Milonakis. He also recently revealed that as a young man, he did porn to pay the bills. You do what you gotta do, we suppose.

11. Shaun Zaken

Shaun Zaken
Next, Meg hooked up with the comedy writer Shaun Zaken, who you may recognize from his role as a waiter on Sex and the City. Upgrade?

12. A Foot In the Door

A Foot In the Door
This was also early in Meg's Hollywood career, and she reportedly very much enjoyed how well-connected Zaken's family was.

13. House In the Hamptons

House In the Hamptons
“His family is well-off with a home in the Hamptons and he had good connections in Hollywood," said one source close to Meg. "She liked that lifestyle and his access."

14. A Bad Breakup

A Bad Breakup
Alas, it did not end well for these lovebirds. An insider says Shaun and Meg fought constantly, and she was heartbroken when they eventually parted ways.

15. Great Expectations

Great Expectations
“She really pursued him because she saw a future with him, but he wasn’t ready for that kind of commitment ... She was broken-hearted by their split," the source claims.

16. Brett Ryland

Brett Ryland
But you can't dwell on the past forever, and soon enough, it was on to the next. After Zaken, Meghan dated the actor Brett Ryland for five months.

17. A Lack of Chemistry

A Lack of Chemistry
“Brett adored Meghan. He was constantly trying to shower her with love and she enjoyed the attention, but she seemed to be in it more for the affirmation," says the insider. “He didn’t have the kind of bravado or high profile she was looking for in a partner. He tried hard but there wasn’t much glamour or huge chemistry."

18. A Familiar Pattern

A Familiar Pattern
“One day the switch just flipped, like it did with (first husband) Trevor, and she called it off. But he is a good guy, so they stayed friends," the source adds.

19. Trevor Engelson

Trevor Engelson
Finally, we arrive at Meghan's first husband, actor and film producer Trevor Engelson. The couple was married just two years, and neither has been eager to talk about their split.

20. The Past is the Past

The Past is the Past
But hey, we all have our pasts, and the only thing that matters now is that Meg has found happiness with the world's most eligible bachelor. We wish Markle - now the Duchess of Sussex - and Harry all the best!

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