The boyfriend Meghan would rather forget: How a 22-year-old Miss Markle dated an award winning PORN STAR among a host of other young suitors

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For any girl on the eve of her wedding it would be a shattering blow, from which recovery would be painful.

For Meghan Markle, eight days before she marries Prince Harry in front of the Queen and the Royal Family and not forgetting a global TV audience of millions, the agony must be even more acute.

Yesterday she awoke to learn details had emerged of a gallery of men she is said to have dated — all of whose identities, until now, she had managed to keep hidden.

But for the presence of one individual, their identity might have barely caused a ripple — after all if a woman of 36 hadn’t had a boyfriend or two, people might have wondered what on earth was wrong with her.

Yet amid the chiselled ex-actors and sports stars who are reportedly former beaux, the figure of Simon Rex stands out.

Meghan's X-rated romance: Simon Rex made porn films before becoming a comedian/ rapper

'Scary Movie 3' actor Simon Rex and French Model Nausicaa are spotted doing a sexy photo shoot

Posing languidly stretched out naked on a bearskin rug, an unlit cigarette dangling from his mouth and with only a puppy to hide his modesty, he seems an unlikely suitor in the life of the poised young woman who next week will become Her Royal Highness and daughter-in-law to the Prince of Wales.

While the photo alone must be embarrassing enough, it is the back story of the model-turned actor, who made his name in the Scary Movie franchise, that really adds to her humiliation.

For Rex — born Simon Rex Cutright and now a 43-year-old comedian and rapper using the name Dirt Nasty — is a former star of ‘adult’ films, the Hollywood euphemism for porn movies.

His first three films were ‘aimed’ at the gay market. Indeed, he claims to have won an award for Best Gay Solo Video in 1997. Rex uses the reclining naked photograph on his Twitter home page where he also likes to post crude jokes. In a reference to engagement rings, he wrote the other day: ‘The bigger the diamond, the smaller the d***.’

Elsewhere there is a picture of him posing in a Coca-Cola costume carrying the caption: ‘I think I have a coke problem.’

All in all, he seems the unlikeliest of romances for Ms Markle. But according to the Sun newspaper, the two enjoyed a date in 2004 when Meghan was 22 and taking her very first steps as a professional actress with walk-on parts in daytime television.

Simon Rex of Dirt Nasty performs at the world famous Roxy theater in Los Angeles, CA

Simon 'Dirt Nasty' Rex (centre) arrives at the grand opening of the Sapphire Pool & Day Club on May 3, 2013 in Las Vegas, Nevada

They are said to have met on the set of a long-forgotten U.S. sitcom called Cuts when they both had roles in the same episode.

He was already a successful model appearing in ads for Calvin Klein, Versace and Levi’s while Meghan was still a year away from her first regular-money role as a ‘briefcase girl’ — holding up a case full of cash — on game show Deal Or No Deal.

Of his past as a porn star — he was 18 and 19 when he made the films — he says it was to pay the bills.

‘I went there and did that s***,’ he said in a 2014 interview. ‘It was just enough to pay the rent at the time. I was living in the moment.’

He added: ‘In hindsight, it wasn’t the best move.’

For Meghan, Rex’s moment of regret will barely register. Instead, any lingering hopes she may have had that her past life would remain off limits as she completes her transformation from Hollywood starlet to royal princess must surely now have vanished.

If it’s any comfort, the Royal Family will scarcely raise an eyebrow at the revelations. As one figure close to the Royals told me: ‘It’s a horrid little betrayal, but it won’t damage her reputation. She’s not a virginal bride like Diana, who was only just out of her teens when she married Charles, but a mature woman of experience with one failed marriage behind her.’

Paris Hilton and Simon Rex at the premiere of the 'Layer Cake' film in January 2005 (left). Paris Hilton and Simon Rex on the set of Pledge This! in Miami, Florida in August 2004

The disclosures have come from Ninaki Priddy, once an inseparable friend of Meghan to whom she had been ‘like a sister’. But their relationship is long over. Since Meghan’s engagement to Harry she has spilled just about every intimate bean of their 30-year friendship.

It was Ms Priddy, you may recall, who revealed to royal biographer Andrew Morton that Meghan ‘was always fascinated by the Royal Family. She wants to be Princess Diana 2.’ Yet what emerges from these revelations is a picture of Meghan who, as a young woman, was not quite the confident and sophisticated figure whom Harry fell in love with. Meghan was vulnerable and as likely as any other twentysomething to chance her luck in the dating stakes.

Until now it had been thought that, for all her beauty, Meghan had been linked to only a handful of men, apart from her former husband, film producer Trevor Engelson and the Canadian chef who replaced him in her affections.

There had been the boy with whom she shared a first kiss, a high-school sweetheart, and a couple of others, none serious. But now we learn that she had a dating bible called The Rules, a self-help book aimed at women who want ‘marriage in the shortest time possible’. Meghan studied the book — an instant bestseller when it came out in the mid-Nineties — so thoroughly she was able to recite passages off by heart.

Andre Legacy and Simon Rex 'Dirt Nasty' perform with Chris Jones at Louis Bar and Lounge at Gansevoort South, Miami Beach, Florida

According to Ms Priddy: ‘Meghan used to quote The Rules all the time and really put it into practice with a number of her boyfriends.

‘She was never without a boyfriend for more than two or three months and always striving to have someone by her side. She liked the idea of being part of a team and having a domestic life.’

Ms Priddy adds: ‘Any relationship that she was in, there was always an element of marriage in the back of her mind.’ Meghan, she says, would quickly be thinking about what the relationship would be like in ten years time. That surely cannot have been the case with porn star Rex. But what of the other figures she has now been linked to?

Unsurprisingly some cover the period when she was away from home for the first time and a student at Northwestern University in Chicago.

Shaun Zaken was an actor and screenwriter with whom she enjoyed a six-month romance in 2003. Both had attended Northwestern and had ambitions to act. Shaun, now 38 and who played a waiter in an episode of Sex And The City, would rehearse his audition lines with her.

According to the Sun they split up because he would not make the commitment she wanted.

‘His family are well-off with a home in the Hamptons [the upmarket resort on Long Island, close to New York] and he had good connections in Hollywood,’ a source told the newspaper. ‘She liked that lifestyle.’

Both were demanding of each other, claims the source, resulting in passionate rows in public. ‘She really pursued him because she saw a future with him. She was broken-hearted by their split.’

Young lovers (left to right): Brett Ryland and Shaun Zaken were both actor/ screenwriters while Steve Lepore was a university basketball star

How interesting that Zaken, now a comedy writer, penned a show last year about a fairy tale Prince Charming in modern-day Los Angeles.

After Zaken, Meghan is said to have dated another actor and writer called Brett Ryland. They were together for five months, but he was said not to possess the ‘kind of bravado or high profile she was looking for’.

According to a friend, Brett, who lives in LA, ‘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 [emotional support].’

They are said to have stayed good friends. During her first year at university, Meghan went out with strapping 6ft 5in basketball star Steve Lepore. Her college friends were ‘impressed that she had snared a hottie’.

The friend said: ‘She was very proud of having landed this handsome guy and happy to share photos of him. She spoke of how broad and beautiful his chest was. Steve was the star of the basketball team. She hadn’t ever dated someone like that.’

Then, after Lepore she is said to have had a nine-month romance with a wealthy fellow student. He is not named, though the newspaper reports: ‘She was very much in love with him, but it was a tempestuous relationship.’

Meghan was said to have been ‘taken by his status’ because his family were wealthy diplomats.

During her university years Meghan did work experience as an intern at the U.S. embassy in Buenos Aires. In 2002, she was said to have ‘caught the eye’ of a wealthy Argentine businessman.

According to the newspaper the encounter was ‘something of a liberation’ for her. She was off in Argentina and had this little adventure on the quiet.’

Interestingly, Meghan was also linked to another American who worked at the embassy. Or at least those are the rumours in the Argentine capital

Interestingly, Meghan was also linked to another American who worked at the embassy. Or at least those are the rumours in the Argentine capital.

Looking back, it does seem these men were little more than footfalls in her romantic history. By 2004, she was with TV producer Engelson. In 2010, they were engaged and wed the following year, to separate two years later.

Ms Priddy claims that her friend had put ‘all The Rules into play with Trevor’.

She had apparently met a fortune teller in Argentina who told her she would marry a man with ‘curly red hair’. Engelson, of course is not the only figure in her life to have reddish hair. So, too, does Prince Harry.

Next week she will have pushed the far-from-welcome disclosures to the back of her mind as family and friends see them marry.

Her old friend Ninaki will not be there. She did not make the guest list.

The rule book secrets that helped her bewitch a Prince 

For every young girl who dreams of growing up and marrying a handsome Prince, there is one burning question. How did Meghan do it?

Just how did this 36-year-old American divorcee and small-screen actress capture the eye of Prince Harry?

Now we know the answer. One of her childhood friends, Ninaki Priddy, this week said Meghan swore by a self-help book called The Rules: Time-tested Secrets For Capturing The Heart Of Mr Right.

Although a bestseller, the book came in for criticism over its anti-feminist message. It advises women to be subservient, let the man to lead the conversation and to never, ever sleep with him until you’ve had at least three dates.

There’s also a chapter on how to attract a high-profile man — along with other rules Meghan may have found useful . . .

SNARING YOUR VIP

What follows are The Rules for meeting and dating celebrities and business bigwigs. Assuming the VIP spoke to you first, here’s what to do and what not to do:

1. Take a deep breath. Stay composed.

2. Treat him as you would any other man, not the movie star or business tycoon he is.

3. Do not stare at him

4. Do not light up or act giddy, as if you just won the lottery.

5. Act as if you’ve been out of the country for the last three years and you’re not quite sure who he is, even if he was just on the cover of People magazine.

6. Don’t ask for his autograph.

7. Don’t compliment him.

8. Don’t show any interest in his career.

9. If you’re an aspiring actress, do not ask for an audition.

10. Do not ask him to do you a favour, such as donate money to your favourite charity.

11. Act interested but not spellbound. Leave him alone. After five minutes of conversation about whatever he wants to talk about, say: ‘Oh, look at the time, I must leave now. It was nice meeting you.’ And walk away.

12. Do not seem impressed by his limousine or entourage.

13. Once you are dating a celebrity, don’t see him whenever and wherever it’s convenient for him because he has a busy schedule. 14. It’s tempting to drop your friends and family and revolve your whole life around this famous man. You must still live your own life, see him two to three times a week — until he proposes.

15. If he’s widely popular, expect that other women might write to him, call him and throw themselves at him. Do not get angry or show jealousy or insecurity. Do not be possessive in public. If he pursued you, their advances won’t matter. He’ll still want you.

16. Be discreet. Do not call the tabloids and tell them you’re dating, as a way of announcing to other women that he’s your man. That would be self-serving, possibly hurtful or embarrassing to him, and might ruin any chances of his continuing to see you.

17. Don’t try to become too friendly with his staff in an effort to keep tabs on him or so they put in a good word for you.

18. Don’t seem overly interested in his wealth or the limelight. Rules girls are not groupies.

DON’T RUSH INTO SEX

You will have to exercise a bit of self-restraint and trust that if you hold off for a few weeks or months you won’t be sorry. Why risk having a man call you easy?

It can be excruciating to put off sex with someone you’re attracted to but you must think long-term.

Let’s say that now, hopefully, you’ve held off for a while and are ready to have sex with him.

What Rules should you follow? First and foremost, stay emotionally cool no matter how hot the sex gets. The fact is that most women turn men off not only because they sleep with them too soon, but because they talk too much about it in bed.

Don’t be a drill sergeant, demanding he do that or this. Being with you in bed should not be difficult or demanding.

Don’t cling to him if he has to leave that night or the following morning.

Be casual and unmoved about the fact the date is over — with that attitude chances are that he’ll be the one hanging on.

LONG-DISTANCE LOVE

Having been introduced to someone who lives in a different city or country, Rules apply to making it work:

Don’t call him. He calls you. Get off the phone in 20 minutes. If he wants to visit you on the weekend, he must ask you by Wednesday.

If he suggests that you meet in his city, or halfway, say: ‘That sounds nice, but things are really hectic right now, I just couldn’t get away.’ He’ll realise that he has to visit you. If you travel to see him before he’s made at least three trips to see you, he won’t think you’re special, and will not pursue you in the future. The first three times he visits, he should not stay with you. The first three visits are really three dates . . . and on the first three dates we don’t have sex.

The first three times, always see a little less of him than he would like. If he suggests flying in Friday night and leaving Sunday evening, say Saturday morning would be better and end on Sunday afternoon.

After he has visited you three times, you can visit him once and stay at his place. If he offers to pay your travel costs, let him. If he doesn’t, don’t ask for the money but let him pay for everything when you’re there. If things get serious, he might ask if you would ever consider relocating.

Until he actually gives you a ring, be vague. There’s no reason to relocate until you’ve set a wedding date.

CLOSING THE DEAL

If you have been following the Rules you will not only get a proposal but you will know where the relationship is going long before he pops the question. You will sense a warm, open feeling emanating from him, a desire to include you in his world.

The way to get a man to ask you to marry him in a reasonable amount of time is not to live with him before you’re engaged, and to continue to see him only three times a week. There’s no cold feeling in Rules engagements. He’s made his decision, he wants to get married, to be with you all the time, for ever.

The Complete Book Of Rules by Ellen Fein and Sherrie Schneider published by Thorson Element at £9.99 © Ellen Fein and Sherrie Schneider 2000.