Rumors say that Prince Harry allegedly tried to date Jennifer Anniston before he met Meghan Markle

We all know that Prince Harry is happily married to former actress Meghan Markle and that they have just welcomed their first son together. But before Harry and Meghan met he was considered quite the royal wild child. Before he decided to pursue Meghan he had a crush on another major Hollywood film star: Jennifer Aniston. Aniston, who is largely thought of like America’s sweetheart is a whopping sixteen years older than Harry and it seemed like it would be an unlikely match but that didn’t stop the rumor mill.

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Meet The Author

Ian Halperin has been a big name in the celebrity biography circuit and through some major digging has been able to unearth quite a few tidbits of information about some of our favorite celebs.

Hailing from the United States, Halperin has profiled the Kardashian Clan, Brad Pitt, and Angelina Jolie’s marriage, and now he has decided to jump across the pond and look at the Royals. Meghan’s induction into the Royal family has finally given him that American celeb edge he needs. But now it is time for Jennifer Aniston.

A Prince Goes Courting

Prince Harry had always been a fan of American cinema and television which means he had grown up watching Jennifer Aniston on Friends and then seen her start showing up on the big screen in a number of movies. As he watched her he knew that he had to meet her.

Keep in mind this was a long time before he would meet Meghan Markle the Hollywood actress that would steal his heart. But at the time, Jen was who he wanted and he knew that he had to meet her. The question simple became, how and what kind of meeting would this be?

The GQ Cover

While Harry had always found Jen attractive with her tanned skin, beach blonde locks, and sparkling eyes, it was the GQ cover which really pushed him over the edge. Jen is featured sitting cross-legged and wearing only a men’s striped tie as she grins beguiling at the camera.

Once Harry saw that it was over, he simply had to meet her. Keep in mind this was back in 2009 well before Meghan entered the picture. Don’t worry about his attention being diverted during this time, he would not meet Meghan for many more years. That is a tale for another time.

Party Animal

We all know that the prince has a bit of a wild time in his youth. Those no infamous photos of him going skinny dipping in Las Vegas were enough to shock the world and the Queen.

But prior to all that, Harry was in Los Angeles hitting up some of Hollywood’s favorite nightlife spots with a bunch of models that had decided to join him on his royal outing. It was during that night that the prince decided he wanted to try and track down Jen to see if she would be willing to meet him. But first, he needed to get her number.

A Naughty Prince

Harry has really cleaned up his act since he got married and started a family but before that, he did some things that were really not up to the royal standard. And we don’t just mean the partying. Oh no, one Halloween Harry made a very poor costume choice when he decided to be a historical figure.

If you’re thinking Napoleon Bonaparte think again. No, he decided to go to a Halloween party wearing an illegal armband and dressed as a member of the former Nazi party that was responsible for World War II. The media had a field day with this and Harry was condemned by the press, obviously.

An Apology

The world was horrified by Harry’s costume choice and he had to draft an apology with the help of the Royal PR team to try and do some damage control.

He realized his error but the damage was done and the photos were splashed across every form of media from newspapers to social media. He had to do some real repair work on his image and start watching exactly what he did to avoid any more major mistakes.

Boozy Billiards

This would not be Harry’s only very public debacle. While he stayed away from any more controversial costumes he did not stop partying. During a stint in Las Vegas, he was once more caught by the paparazzi or someone leaking photos they shouldn’t partying it up in a private sweet.

This would not have been a big deal, except that he was nude the entire time and playing billiards. Once more a scandal erupted around the prince.

Damage Control

You would think that the prince was young when all of this was happening but he was actually 28 when these photos were sent off to the press.

The Queen was absolutely horrified that her nephew was making headlines for all the wrong reasons and decided to have the Palace tell the media that they could not continue to print these photos or they would be sued. The problem is that once something is online it’s really there forever.

His Excuse

After those photos broke, Harry was immediately summoned to Buckingham Palace by Prince Charles and Queen Elizabeth for a very stern talking to. One inside source allegedly reported that his excuse for the whole event was that Las Vegas is very hot.

Yes, that seems like a likely story Prince Harry what with you being in your climate controlled sweet at a hotel. We’re pretty sure the Queen did not buy that excuse.

The Party Doesn’t Stop

This was only one of many instances, two years before he was caught in Vegas he was also snapped while being extremely inebriated in Croatia. He had just gone through a break-up and it seemed the answer was to drink way too much, dance the night away, and go swimming in all of his clothes.

All we can say about this is that it’s good he kept his clothes on this time since there were a ton of people taking pictures that night.

Was Jen Interested?

With Harry being so much younger than her, and no doubt she had heard all about his exploits both in the States and abroad it seems likely that she would not have found him very appealing.

As a woman with an established career, long term relationships, and basically a maturity level Harry did not seem to possess it is no wonder that things did not work out between the two. So where was Jen while Harry was out partying in the streets of Los Angeles?

Jen’s Love Life

Harry was busy being young and living large but Jen was very focused on her career in 2009 not to say that she isn’t still focused on it. But the time Harry wanted to date her was particularly busy.

She had four major movies come out between 2009 and 2010 and had two relationships with a very well-known actor and a singer-songwriter. Who was she dating you might be wondering because it certainly wasn’t Harry.

Jen’s Boyfriends

Jen was pretty busy work wise and love wise as well. In 2009 she dated singer-songwriter John Mayer for just under a year which seems like a feat itself as this guy has dated half of Hollywood with Katy Perry and Jessica Simpson being in there.

Gerard Butler was also rumored to have been with Jen after they filmed The Bounty Hunter together the following year, although this has never been confirmed by either of them.

A Major Loss

Jen found John Mayer’s social media use, specifically Twitter simply too much to handle which is one of the reasons the two didn’t work out. Mayer maintains that Jen was his dream woman and even though things didn’t work out he was happy that he at least got the time they had together.

But what exactly is it that makes Jen so special that the men of Hollywood and even Royals seem to fall at her feet?

The Peoples’ Princess

It seems like Harry had heard the rumors about Jen not just for her beauty but the fact that she was down to earth and a genuinely great person to be around. Clearly all the men in Hollywood seemed to think so as they were begging for her to date them.

Harry would not be left out of the mix and one source close to the Prince reported that he thought she might be the next princess to enter the royal family.

The Number

Eventually, through a lot of finagling and schmoozing Harry managed to find someone willing to give him Jen’s phone number. He was beyond thrilled that he finally had a direct line of communication to what he hoped would be his future princess.

Now, you would think that Harry would have tried to approach her or at least message her like an adult and ask her out. Sadly, the prince showed his age and messaged her the way no grown woman wants to be approached.

Emojis

We don’t know exactly what Harry was thinking but Halperin says in his book that the prince did not text Jen a message asking her how she is or what she’s up to. No, instead he selected a series of emojis and sent those to her instead.

What she was supposed to infer from those we don’t know but we can only assume that Harry had either had too much to drink, was very nervous or possibly a combination of both.

What Was He Thinking?

Clearly, Harry has done a lot of growing up since then or perhaps Meghan Markle really enjoys emojis. We hope that’s not what won her over. Nobody knows for sure which emojis he used, maybe Halperin’s book will tell us.

But if the prince has been drinking we can only imagine how bad they must have been. Let’s just imagine he set a waving hand or a smiley face rather than something like a peach or a winking face.

Did Jen Respond?

We don’t know for sure what Jen said or if she responded but there are sources who have reported that she did receive the message. Jen was not interested primarily because of his age and the fact that they were at completely different times in their lives which would probably make them incompatible.

But really it just sounds like she wasn’t interested in getting involved with a prince who didn’t want to grow up.

False Claims

Jen has decided to come forward and inform the press that nothing regarding Prince Harry’s alleged infatuation with her is real. She does not want any bad press for herself or the Prince who is now very happily married and we respect that.

Halperin though claims that everything in his book is true. Of course, he would claim this as he does want to make some sales but who can know what is true and what is not.

Staying Quiet

Nothing has been heard from Buckingham Palace regarding Prince Harry’s former Jen obsession which makes sense since if they did send out a press release it would further work to back up the claim. Also, Harry is married now so what does the past matter.

If he wanted to meet Jen and didn’t oh well. Even royals don’t always get what they want and maybe that was a catalyst for Harry to grow up and meet Meghan.

Are You Going To Read The Book?

This book of Halperin’s sounds like the kind of sensationalist material that only diehard Jen and Prince Harry fans will purchase. In this day and age, people can simply Google the information they want and it will probably be the same or on par with what Halperin is putting out there.

We will admit though that we do plan to watch the documentary just to see what kind of fun tidbits might pop-up, and maybe some of it will even be true.

Happily Ever After

Jen is off making movies as usual and Harry is now married with a new baby. You should definitely look into how Harry’s life has vastly changed during this time and how he is starting to make a name for himself through his philanthropic work rather than for being caught partying or in a state of undress.

He has come a long way in a short amount of time, so good on him for getting his act together!