22 Pics Of Prince Harry Before He Decided To Settle Down

The Royal Family have been crossing their fingers that one day, Prince Harry will settle down with a nice girl. Though she may not have been what they expected, Meghan Markle stepped up for that role to win over the former playboy's heart. No one will ever forget the worldly reputation he built for himself back when he was single. Prince Harry was that naughty ginger who was a total cad with women and a rowdy party boy. His rascal-like antics were enough to make the Queen cringe and give him a talking to behind closed doors.

Prince Harry's party boy ways were entertaining and gave the media a field day to make stories out of. However, there were a few times that he did cross the line when it came to royal behavior. Though no one will ever know, his family probably scolded him more than once. We will applaud both Harry and Meghan for defying royal conventions and redefining what it means to be a modern-day couple in a traditional place such as Buckingham Palace. Before he walks down the aisle in May, let's take a walk down memory lane and reminisce about the times when Prince Harry was a single playboy who was ready to paint the town and have a good time.

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22 Don't Worry, Be Happy

E! Online

Throughout the years, Harry prided himself on being the royal bad boy. After all, he is only second in line after Prince William so that means that he's allowed to be the silly one whereas his older brother has to be the responsible one. No matter what kind of trouble he got himself into, people adored him even more for it because he was just too much of a silly character. He is always upbeat with a big smile on his face and he is kind to everyone around him. If you didn't know he was a Prince, you would think he is just a cute guy in his '20s who is just down for a good time. Here, he is getting silly with some security guard trying to get a rise out of him.

21 Shhh It's A Secret

Daily Mail

The then 27-year-old cozied up to some mystery brunette girl on a Vegas trip. Chances are that he probably randomly met her at a pool party that very day. She was probably thinking, "Oh my God! What are the chances that I will ever get to hang out with Prince Harry?" For real though, who in their right mind would ever turn down that opportunity? Even if you don't end up pulling a one-nighter with Prince Harry, it still makes for one hell of a story to go home and tell your friends how you partied with him. They will be envious when you tell them that you got to sit on his lap in a hot tub. This lucky girl can safely say that she had a "moment" with the Prince.

20 Big Pimpin' Since '97

NY Daily News

The adorable young 13-year-old Prince couldn't help but blush when he was enjoying the company of the Spice Girls in 1997. He got to meet them at their concert in Johannesburg, South Africa. Baby Spice (aka Emma Bunton) was his favorite one and she held his hand and kissed him tenderly on the cheek. This was sure to cheer him up since this was one of his first public appearances since his mother's funeral that happened tragically earlier that year. Sometimes, all a preteen kid needs is some attention from some foxy older women in order to boost his confidence. Clearly, this did wonders — just look at the game that he has now with the ladies! It is always better to start them out young.

19 Back In His Dorm Room Days


In 2003, Prince Harry attended Eton College which is an all-boys boarding school in Berkshire England were boys age 13-19 attend. Of course, it has a pricey tuition and only young boys from well-off families can afford to go there. Naturally, this is where the Royal Family put both William and Harry so that they could get the best possible education that England had to offer. Here, a teenage Harry is pictured sitting at a desk in his dorm room with a beautiful portrait of his mother, the late Princess Diana. This is where we see Harry's more vulnerable side where he isn't such a bad boy. Prince Harry later revealed that he "didn't enjoy" Eton and that he “wanted to be the bad boy” as he visited a Cape Town youth center that works to rehabilitate gang leaders.

18 Getting Flushed In The Face

Daily Mail

This pic clearly demonstrates Prince Harry living up to the rambunctious image that the press feeds international news sources. He is yelling something here at the top of his lungs and pointing at something that has caught his eye. With a table of never-ending drinks in a VIP room somewhere, Harry's face is flushed. It is half because he is a redhead with naturally fair skin that blushes easily and the other half is because he is intoxicated. Maybe there is some hot girl in the room who he is trying to summon or there is something hilarious going on that we don't know about. He is in his early '20s in this pic living the rockstar lifestyle long before Meghan came into the picture.

17 Not Sure What To Do With Her


There were times when Prince Harry was not single back in his younger years. In fact, he was in a long-term seven-year on-again-off-again relationship with Chelsy Davy. Chelsy Davy is the daughter of a wealthy Zimbabwean farmer. In this pic, there are some telltale body language signs here. She is trying to get his attention by whispering in her ear at a rugby game they are attending. He is staring off into space in ambivalence almost wishing that she wouldn't be nagging him. After their breakup in 2010, she opened up about her relationship with Prince Harry to the press. Davy admitted that "some people are definitely better' at dating royals than others." She revealed that being chased by photographers desperate to capture images of the couple together was terrifying.

16 Chasing Some Tail


In 2012, Prince Harry was in trouble once again after another royal scandal broke out after being pictured naked in a Las Vegas hotel. Two pictures of him of appeared on TMZ showing Harry playing strip billiards with six young women. Though those pics are a little too inappropriate for TheTalko, feel free to Google these if you are so curious. In this pic, he is pictured again with these women either before or after playing the game of strip billiards. He obviously likes what he saw because he is chasing this hot blonde in a bikini around. Prince Harry needed some R&R because this was fun time in Sin City before heading off to serve in Afghanistan. At this point in time, anything the "Party Prince" did was hardly shocking.

15 Boy's Night With Ryan Lochte

Hollywood Reporter

Lest we forget, all the fuss that was made about Prince Harry exposing his crown jewels in Las Vegas was accompanied by his bromance with Olympic medalist and competitive swimmer Ryan Lochte. Their bromance was brief and short-lived since Lochte told the Today Show that he had never met the Prince before that infamous night. "We were at the same pool party, and his people came over to my table and said, 'Hey, Prince Harry wants to meet you.'" If Prince Harry wants to party with you, that is an offer that no human being could possibly refuse. Lochte goes on to tell the story: "He was like, 'You want to race me in the pool?' I was like, 'All right, let's go.'" Later they were seen in a pool full of women in bikinis and the rest is history.

14 Just Another Excuse To See Him Shirtless


Prince Harry always looks like he is in shape but he never looks too jacked. In any case, a shirtless pic of Prince Harry is always more than welcome on our list. In this pic, it is uncertain whether is doing a goofy dance impromptu or if he is just moving around and the paparazzi just snapped him in mid-movement. This is one of his more chill pics on our list but Prince Harry always used to look like he was up to no good when he was out and about. When he wasn't at some well-to-do royal event, he was on the prowl. Sorry, Harry. Those sunglasses can't hide you or disguise you. You stand out from the crowd whether you want to or not.

13 Ain't Nothing More Ballin Than A Top Hat

Celeb Buzz

In 2014, Prince Harry was looking dapper AF on a fine summer day when he escorted his grandmother, Queen Elizabeth to his first ever Royal Ascot races. British fashion can look so campy to us Americans, but only Prince Harry can pull this look off without looking like a dork. He even wore a mismatched 3-piece suit with that hat as a signature accessory. There is a time and a place to wear anything and an old-fashioned British traditional festivity is the perfect place for a top hat. If he were to wear that on the red carpet, now that would be a different story. Like a perfect gentleman, he rode with the Queen in a horse-drawn carriage and kept her company the entire day. Prince Charming, indeed.

12 Just Take A Look At That Mischievous Grin

E! Online

In 2012, Prince Harry did the honor of being dispatched around the globe in honor of the Queen's Diamond Jubilee. In England, the Diamond Jubilee of Queen Elizabeth II was a multinational celebration throughout the year of 2012 that marked the 60th anniversary of the accession of the Queen on February 6th, 1952. The last time there was a Diamond Jubilee was back in 1897. This meant that Prince Harry got to do some island-hopping beginning with Belize and ending with the Bahamas. He appeared coming out of the plane in the Bahamas with this crisp white ceremonial uniform. Being the eloquent public speaker that he is, he got to meet with the local officials and Miss Bahamas and deliver a speech on behalf of his grandma. We could listen to hours of him talking in that accent.

11 What Happens In Vegas Stays In Vegas

The Huffington Post UK

Alright, so we are going to revisit that infamous 2012 Vegas trip because it was just too eventful that we just can't shake it from our memories. Also, we want to just feature Prince Harry shirtless as much as we possibly can. Believe it or not, this pic was one of the more tame ones that were leaked in the media before his naked pics were leaked to TMZ. Since Harry was with a group of his bros, we certainly hope that he was the only one in the group donning a Fedora hat. After all, you can only have one Fedora per group. Prince Harry is getting wet and wild in this daytime picture but this is just the pre-game before the strip billiards that would be later to come.

10 Dirt Off Your Shoulders

Rant Now

Prince Harry is caught chatting with yet another girl, which is no surprise. She was probably just passing him, looked over and realized "wait...is that? No, it can't be. Oh wait, it is. It's *gasp* Prince Harry!" This passerby probably just wanted to get a quick pic with him before the paparazzi snapped them standing next to each other. If you go to Vegas, attend a pool party, get hammered then any redhead in your path could very well look like Prince Harry so you would definitely have to do a double take without looking like an idiot. Women approaching him ain't no thang for Harry because he is just brushing the dirt off his shoulders like Jay-Z. There is probably a volleyball pool game that he is missing out on by talking to this broad, hence the inflatable volleyball.

9 Players Gonna Play


Look at the way all these women are just lining up to meet and greet with the handsome Prince Harry. They are all smiles and cheer somewhere at a British event were you have to wear hats and wear springtime colors. It is as if they are all waiting for their turns to have any one-on-one time that they can. Prince Harry would have made the perfect contestant for The Bachelor if he really wanted to, but he is too cool and high-profile for that. These ladies clearly don't mind sharing him and his attention because any kind of attention you can get from Harry is something to write home about. He is trying to look humble but he knows deep down that the spotlight is all on him.

8 Didn't Take England's Loss Too Well


Back in 2004, 20-year-old Prince Harry couldn't exactly contain his alcohol and self-control. He got into a drunken brawl with a photographer outside a London club. A rep said that he was merely "pushing the camera away" but that blew up into headlines shortly thereafter. Granted, we can't imagine how annoying and invasive it must feel for celebrities have the paparazzi follow them around and blatantly harassing them for any shot. In fact, the paps purposely want to get a reaction out of the stars that they are targeting because they see nothing but dollar signs. His behavior isn't any different from many other male celebrities who had just about enough of the paparazzi stalking them before their fuses blew out and they exploded in temper.

7 Macking On A Brazilian Model

Heart Radio

Not only is Harry a Prince and soldier, but he is also a talented rugby player. In spring of 2012, he was on the winning team at the Sentebale Royal Salute Polo Cup, besting his opponents astride a horse 6-3 in a charity match held just outside Sao Paulo. To cap off the last event of the tour, he was presented with a champion's cup by the stunning Brazilian model Fernanda Motta. Of course, he had to snag a kiss from her and flirtatiously tousle her hair around in the most playful manner. She was flattered yet taken aback at the same time because looking at the body language, this was clearly unexpected. Prince Harry likes to lay those surprises on pretty women that cross his path.

6 Even As A Young Teen, He Was A Ladies Man

Getty Images

This photo takes us way back to Prince Harry's teenage years and it caused some foreshadowing into his future full of women and debauchery. These three blonde ladies are all sharing the company of the young Prince at The Beaufort Polo Club and he has all three of them to himself. It looks like a chilly day but that doesn't stop anyone from enjoying the outdoors for a game of polo. Gotta love that old school BMW that he was using as a way to impress the chicks. No doubt that these girls were target practice for more women that would find their way into Prince Harry's life at one point or another. Meghan Markle would look at these pics and either laugh or cringe. We can't decide.

5 Harry Joining The Hitler Youth


Back in 2005, Prince Harry stirred up controversy and criticism after he was spotted wearing a Nazi uniform at a private Halloween party. Though he was only 20 years old at the time, all eyes in the world were on him and it is a safe assumption that he brought shame on the Royal Family. Out of everything that he has ever done, this was the biggest stunt that got him in the most trouble and made the Queen's head spin. His late teen years were characterized by a facility for "hell-raising", including excessive drinking, cannabis use and taking a swing at photographers, but this one took the cake. After offending the Israeli prime minister, calls began for strip Prince Harry of his place at the Royal Military Academy. Those calls all fell on deaf ears. This is one incident that he probably looks back on the most with regret.

4 Ginger Man In Afghanistan


Prince Harry has served two tours in Afghanistan in the British army rising to the rank of Captain over the course of ten years. This is a surprising fact that many people are not aware of because when you think "royal", you typically think of someone that is just joining the army out of courtesy. What makes Prince Harry even more desirable to us women is that he is a real-life war hero having saved many Afghan lives from Taliban attacks. Here, he has some down time getting all sweaty in the desert kicking around something that resembles a soccer ball. Hopefully, he doused himself with sunscreen because that fair skin doesn't do very well in the Middle East when the sun is at its peak.

3 Who Doesn't Love A Man In Uniform?

She Knows

Women since the beginning of time have been attracted to men in uniforms, especially military uniforms. Just when we think that Prince Harry can't get any hotter, we get this curveball. That automatic weapon makes him look dangerous and just adds to the appeal. For those ladies who have fantasized about their men taking them out to a shooting range should just stop what they are doing and ogle this pic immediately. Though he is doing his service and not goofing around in this pic, you can bet that he used this as ammunition (no pun intended) knowing that women all over the world were going to see this and swoon. The dichotomy of a Prince serving in the army among commoners gives him a humble vibe that earns some street cred and respect.

2 And Another One For The Road

E! Online

In all seriousness, war is not a pretty thing and most soldiers who have to endure don't typically leave it unscathed. Not even Prince Harry is an exception to that. At the end of his four-month tour in Afghanistan, he admitted that he killed insurgents while piloting his Apache helicopter. His biggest reason for committing so much time to the Army was because he craved a life out of the spotlight and got frustrated with the tensions and pressures in being a royal. He has also publicly revealed his disdain for some sections of the media and felt the pressure from his father to behave more like a member of the royal family. Prince Harry has always marched to the beat of his own drum and has stayed true to himself no matter what anyone has told him.

1 Just Can't Tolerate The Paparazzi Anymore


In 2006, Prince Harry got found himself in another incident with photographers. Only this time, he had the last laugh. Reps denied that he got into a scuffle with this paparazzi outside Boujis nightclub in London. A palace spokesman said, “There was no aggression intended, there was no confrontation and everyone was laughing about it at the time.” The Prince reportedly chased photographer Nirach Tanner, swore at him, and shoved him. Then, he tumbled on the floor of his car. Though it is clear that Harry is not a fan of the paparazzi, he might have just been having some fun with them by chasing them around. You know, sometimes you need to law down the law and show them who is boss. He is royalty after all.

Sources: Daily Mail, The Guardian, Telegraph, The Sun, E! Online, The Cut, Just Jared

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