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22 Pics Of All The Women Leonardo DiCaprio Has Been With

It is no secret in the world of celebrity gossip that Leonardo DiCaprio is a cad and an infamous playboy. But guess what? We still love him anyways. He stole our hearts when we were merely children (or not even born yet) in Titanic, and he has kept it all the way through The Departed to The Revenant. Though he's only won a single Oscar, it is hard for anyone to feel bad for him because he always and we mean ALWAYS has a beautiful young hottie on his arm. Typically, they are a hot, blonde supermodel, but sometimes he likes to change it up every now and again.

Just like George Clooney back before he met Amal, Leo DiCaprio likes to live the ultimate bachelor lifestyle experimenting with as many beautiful women as possible. Though he has proved himself to be long-term relationship material (there is one hottie on this list who stole his heart for 5 years), he prefers to be single. Really, who can blame him? He has all the money, fame, charm and good looks in the entire world that he will never need to settle down until he is well into middle age. If that time comes for Leo, it will probably be with a 30-something year old lady when he is well into his '50s who shares the same passion for environmental rights as he does. But for now, let's take a look back on all the seductive women that Leo has been with over the years in chronological order starting with the most recent.

Paper Mag

22 Camila Morrone - Leo's Current Beau

Wassup Celebs

In order to woo Leonardo DiCaprio, you have to at least 15-20 years his junior nowadays. 20-year-old Argentinian model/actress Camila Morrone is following in her mother's footsteps of dating famous Hollywood actors. Her mother, Lucia Sola who is a well-known actress is the ex-girlfriend of Al Pacino. Recently, she was spotted getting off a private jet with Leo after a holiday vacation in Aspen, Colorado along with Tobey Maguire and his two kids. She had kept her Instagram followers updated with pics from her snowy vacation. Her upcoming movie will debut at the 2018 Sundance Film Festival so perhaps this whole getting involved with Leo thing is more likely than not a publicity stunt. Either that, or she truly believes that she will be the one to tame him. Good luck with that, honey.

The Sun

21 Nina Agdal - The Latest Heart Broken By Leo

OK! Magazine

24 year old Sports Illustrated model Nina Agdal and Leo were first spotted together in May 2016 and broke up around July 2017. During that 14-month period of time, they were jet-setting around the world together living the good life. The two spent more and more time with each other as the relationship progressed from beach days in Malibu to yacht parties in Ibiza. They always seemed to be on the go taking vacations together over the course of just over a year. They weren't too shy with their PDA either. A source revealed that they were seen out in NYC at Gotham Bar and Grill where, "They were kissing. Like, right out in the open at the table.” When DiCaprio turned 42 last November, Agdal was on hand for a special trip to French Polynesia with him and his mother, Irmelin Indenbirken, according to People.

You have to wonder what exactly went wrong. No one will ever know.

heavy.com

20 Ella Ross - She Upgraded From Scott Disick

Entertainment Tonight

Leo DiCaprio and Scott Disick have a lot in common when it comes to the women the choose to date. The prerequisites are that they are young, beautiful and model material. Unlike Scott, Leo is not a baby daddy so his modelizing ways are not as shameful. Shortly after the breakup with Nina Agdal, it was rumored that Leo moved on Scott Disick's ex, Ella Ross. After splitting with Nina after dating her for one year, he just got right back on the horn and caught the eye of this hottie. Entertainment Tonight speculated that literally just one day after the breakup, Leo moved on to Ella Ross right after she broke up with Scott Disick. It looks like those two were probably just using each other as rebounds.

Got Celeb

19 Rihanna - More Likely They Were Just FWB

India Today

Rihanna and Leonardo DiCaprio have had a platonic(ish) friendship for a long time and they have always supported one another. Let's be honest, Rihanna just isn't Leo's usual type that he goes for. It is not to say that she is not attractive, she is just no supermodel. Rihanna has had a turbulent relationship with Drake over the years, so it is probably refreshing and fun for her to be able to hang out with Leo. Rihanna and Leo were spotted enjoying Neon Carnival at Coachella in 2016. Though they never arrived together, their actual time spent together was more than just "oh hey! what a coincidence" type of moment. He was single and she was single. Why wouldn't they mingle? According to sources, their body language was flirtatious to say the least.

theybf.com

18 Ela Kawalec - Eastern European Goddess

Plotek

One of Leo's favorite things to do is to dress down and just go out and about in New York City. New York City is most people's favorite city in the world if they have ever been there. What makes it more enjoyable is the company of a beautiful woman. Ela is a Polish model who is signed to Elite Model Management in Miami and probably had some gigs in New York as she was seeing Leo in the spring of 2016. Before they were seen cycling through Central Park together, the couple dined al fresco with his pals, but Leo could not keep his eyes off the blonde Eastern European beauty. According to Page Six, they were spotted at different venues partying together in various venues all over the city.

DNA – Global events

17 Roxy Horner - British Blonde Bombshell

Celebuzz

In early 2016, The Sun stated that Roxy and Leo had got cozy during a night at Chiltern Firehouse while he was in London for the BAFTAs. Leo was rumored to have spent a night with Irish TV presenter Laura Whitmore the night before he invited Roxy and her friends back to his hotel. Though Roxy as adamant it was friendly, come on. You don't just take an invitation from Leo DiCaprio to a hotel room just to "be friendly". Or maybe you do. After all, it makes for one hell of a story and free publicity to maybe get a few modeling gigs out of it.

Roxy Horner is known to have dated a few musicians and other celebrities besides Leo. She once dated Towie star Joey Essex and has been linked to musician Jake Bugg after her breakup with Leo. At least she is independent enough to move on after he had her way with her.

Daily Mail

16 Chelsey Weimar - An All-Natural Dutch Beauty

giornalettismo.com

Damn, Leo's girls just keep getting younger and younger. If he goes any younger, he will be arrested for hitting on high school girls. Jokes aside, Victoria's Secret model Chelsey Weimar was all of 19 when she started to get involved with the 40-something Leo. That part is not that surprising, but she is the first brunette to grace this list before a string of blondes enter Leo's life. Dutch beauty Chelsey Weimar is an extremely successful commercial model whose baby face has graced the glossy pages and website of VS Pink. Though she never posted any pics of Leo on her Instagram, some "inside sources" alleged that a few of her Instagrams were taken from inside Leo's Malibu abode. It will only be a few more years until Leo has the option of legally dating a model who wasn't born in the same century as he was.

papermag.com

15 Kelly Rohrbach - Yet Another Sports Illustrated Calendar Girl

US Weekly

Kelly Rohrbach snagged the coveted role of CJ Parker on the Rock's Baywatch remake which is a huge consolation prize after being dumped by Leo in January 2016. She found out the exciting news around the same time she realized that she was no longer Leo DiCaprio's girlfriend. They were first linked in June 2015 and split as their work schedules meant that they were spending too much time apart. This seems like a more amicable reason to split as there is no wrongdoing on either side. In fact, that is incredibly common with most Hollywood couples.

A source told the US Weekly: 'It was mutual. They both have intense work schedules and a lot going on in their lives right now. They both needed to take a break because of that. 'They are still friends and talking but it’s over.'

si.com

14 Toni Garrn - Rekindled Her Flame

In Touch Weekly

Leonardo DiCaprio is one of the few men in the entire world who has the ability to keep all of his gorgeous supermodel exes in a rotation and then pull them out of the cabinet at any convenient time that he choses. In September 2017, he was spotted holding hands and getting cozy with his model ex-girlfriend Toni Garrn in New York City during New York Fashion week. After he had recently been linked to German model Lorena Rae, they were all lovey-dovey strolling around for a night on the town. They enjoyed an 18-month romance from May 2013-December 2014 and still manage to remain friends. Or friends with benefits more likely than not. Usually, whenever an ex texts you wanting to get drinks, you blow him off but secretly revel in the fact that he still wants you. Not unless that ex is Leonardo DiCaprio, then you just drop whatever you are doing to meet up with him. Because why wouldn't you?

Twitter

13 Alesia Riabenkova - His Most Unique Looking Girlfriend

CinemaRx

Though typically, Leo's girlfriends need to be young, beautiful, blonde models...he will go for a young, beautiful, brunette model every now and again. Alesia Riabenkova has a striking appearance that is so unique that you probably have never seen anyone who even remotely resembles her. The Latvian exotic beauty has appeared on the covers of Glamour and Elle. After a brief fling with Leo in 2013, after she dated British actor Gerard Butler from 2012 to 2013.

Alesia Riabenkova has been involved in some controversy. In January 2015, Riabenkova then made the shocking claim she was impregnated during the alleged assault and wanted an abortion. A DNA test confirmed the baby was not the photographer's. Ultimately, it was his word against hers and his attorneys claimed that she falsely accused him.

celebritynstars.com

12 Margarita Gauchet - A French Brunette Turned Blonde

zimbio.com

For some time after filming Wolf of Wall Street, Leo announced that he was taking some time off from acting but that never stopped his steamy love life. At around the same time, he started to court 20-year-old French model Margarita Gauchet. She caught Leo's eye on the set of Wolf of Wall Street and a source said that he asked co-star Jonah Hill to score her number. Leo rang her up and invited her to his annual New Year's Yacht party in Australia. If a dude invites you to a party initially rather than asking you to dinner or at least drinks, then it would seem like a casual invitation. These ladies are probably intelligent enough to know that when you get with Leo, there is a limit on the relationship. Or are they?

Listal

11 Miranda Kerr - Short-Lived Speculation

MTV

Back in late 2013, Victoria's Secret model and single mom Miranda Kerr was a newly single after having recently divorced Orlando Bloom. He was spotted out and about at the Sushisamba in the Palazzo in Las Vegas with her after he dumped his on-again, off-again girlfriend Toni Garrn. Seeing as though he was then spotted a week later again with Garrn at a Kanye West concert in Madison Square Garden, they probably reconciled. Perhaps Miranda Kerr was just a party friend to hang out with to share their breakup woes with. There is only heavy speculation over this, so there is a good chance it may or may not have been romantic. Now, she is happily married to Instagram mogul Evan Spiegel and expecting a baby with him, so her ties to Leo are of little to no importance now.

Elle

10 Erin Heatherton - Fling With A Midwestern Cutie

popsugar.com

This is another one-year relationship Leo managed to maintain. You can't exactly say he's too non-committal but he will move on if he doesn't think that the relationship is working out. Victoria's Secret angel Erin Heatherton dated Leonardo DiCaprio from 2011 to 2012 and she doesn't have any regrets or bitterness about it. She told Daily Mail Australia: "He's a wonderful person and he's a friend of mine, I wish him all the best." The 26-year-old model who was raised in a Jewish family in Skokie, Illinois was said to have been devastated when her romance with the modelizing Leo had to come to an end. Though there is no bad blood between them, you have to wonder if her heart is still secretly broken.

Chalkboard Mag

9 Alyce Crawford - She Insists It Was Only Casual

Ella Hoy

Leo DiCaprio was linked to 21-year-old Alyce Crawford who was a contestant on Australia's Next Top Model back in 2011. This was a convenient time because he was staying in Sydney while he was filming The Great Gatsby at the time and she happened to live in the same city. She would visit him regularly at his hotel. This was another trivial and casual fling because he didn't exactly put her at the pinnacle of his social life. According to Australia's Daily Telegraph newspaper, he texted her when he wants to see her and they hook up a few times a week. They've mostly met up during the week. He did other things on weekends. Perhaps there is a good reason that Leo likes them young. They are more content with having short-lived affairs.

Scoop Management

8 Blake Lively - Before There Was Ryan, There Was Leo

NY Daily News

When Blake Lively and Leonardo DiCaprio first got together, the press went wild because it looked like that she would finally be the one to tame his single-guy ways. Alas, it was just merely a summer love that ran its course and came to a graceful end. It all started when they stepped out together at the Cannes film festival in 2011 and called it quits after a blissful summer together. They were seen galavanting in France and Italy even Disneyland before Leo returned to work to work on the set of J. Edgar. A source said it was distance and timing that caused their split even though they had great chemistry. Shortly thereafter, Blake met Ryan Reynolds and the rest is history. We wonder if Leo looks at them with a bit of envy deep down.

US Magazine

7 Bar Refaeli - Long Term Relationship That Set The Bar For Other Blondes

Page Six

Bar Refaeli and Leonardo DiCaprio managed to sustain their relationship for five years, which is a long time in Leo years. The two dated from 2006-2011 and it looked like Leo had finally found "the One." Bar Refaeli is a natural beauty and looks radiant even without any makeup on so she definitely set the bar high for any future blondie girlfriends that he dated after her. Their relationship was so on-again, off-again because it turned out that neither one of them was ready to settle down because it just wasn't their time. They both had busy careers that had been taking them in different directions. After they broke up, Bar married businessman Adi Ezra and got pregnant with her first child. Perhaps a relationship with Leo teaches you a few lessons of what you want your future husband to be like.

popsugar.com

6 Gisele Bündchen - The Famous Five Year Relationship

popsugar.com

Gisele Bunchen and Tom Brady are known as one of the biggest power couples in all of Celebrityland. They have been happily married for 9 years and have two beautiful children together. In the early '00s, Gisele Bunchen and Leo DiCaprio were one of the most talked about couples in the tabloids. They were the it couple from 2000-2005 when he was one of the biggest actors and she was one of the biggest supermodels of the moment. Together they looked absolutely perfect and people started wonder when they were going to hear wedding bells.

He met her at one of her runway shows and they hit it off from there. She even moved to LA in order to be with Leo but that didn't end up working too well for her. She said: "I moved to L.A. for love. I was in a long-distance relationship and I wanted to be close to him. This was the first love of my life, so that was it: ‘I’m moving, I’m in love.’ But now it’s been four years and it’s been hard. I’ve had to cancel a lot of jobs." She eventually had to move back to New York and sadly they broke up.

allure.com

5 Naomi Campbell - Quick Little Fling In The '90s

People

Back in the day, Leo DiCaprio didn't always go for women who were too young for him. Back in 1995, he had a brief fling with Naomi Campbell who was actually four years his senior. Though the fling quickly fizzled and the two still remain close friends today. Even to this day, they are sometimes seen out and about at big events like the Cannes Film Festival, especially after Leo has gone through one of his many breakups with whatever hot blonde model flavor of a few months. What Naomi Campbell and Leonardo DiCaprio both have in common is that they are both notorious party animals so that has given them something in common in order to sustain their friendship for all of these years.

Pinterest

4 Demi Moore - Before Ashton Ever Happened

happenings.com

Fun fact: Leo and Demi share the same birthday on November 11th, except she is 12 years older than he is. Sometimes even Leo likes to change up his routine and sometimes go for older women. It was rumored that while Demi Moore was going through her divorce from Bruce Willis, she and Leo spent some time together. Though it was probably a fling that never grew into anything more, they were still two gorgeous Hollywood actors that both happened to be Scorpios. This allegedly occurred back in 1997 back when Leo was only 23 years old so it is safe to assume that he was used to be Demi's boy toy for the time being. Sometimes, a cougar just needs to play around in the jungle and target younger dudes. Ain't nothing wrong with that. If men can do it, why can't women?

Fandango

3 Kristen Zang - His GF Before He Shot To Stardom

People

Back in the '90s, baby-faced Leo dated Kristen Zang from 1996-1997 for 15 months before he shot to fame in Titanic. He brought her as his date to the premiere of Romeo & Juliet. We wonder how it must have been like for her watching him in all those romantic scenes with co-star, Claire Danes. After their breakup, it was reported that Kristen dumped Leo because she just wasn't impressed by his immature antics, party boy ways and his group of guy friends and that he needed to "grow up." There is no no-name actress in the world that could have ever gotten young, wild and free Leo to be under her control. Sorry honey, but Leo DiCaprio is in no need for being tamed.

Imgrum

2 Claire Danes - At First, They Hated Each Other

People's Choice

This romance was one that started with dislike and ended in a brief romance. Claire Danes was only 16 when she was casted for the role in Baz Luhrmann's popstastic 1996 adaptation of Romeo & Juliet, but that did not stop her from finding her 22-year-old costar irritatingly immature. Back in the '90s, Leo DiCaprio wasn't afraid to show a little lighter side on set and that just got on her nerves. At the same time, Leo found young Claire to be annoyingly reserved and uptight. Then there were all those steamy romance scenes between them and there was some undeniable chemistry. Apparently, that chemistry transferred off the set of filming because the two reportedly had a brief fling after the filming wrapped. The key word being "brief." Big surprise there.

US Weekly

1 Bridget Hall - Even As A Young Teen, He Was A Modelizer

People

In 1994 when Leo DiCaprio was merely 20 years old, he was starting early by getting with supermodels. At that time, he was enjoying a fling with supermodel Bridget Hall. According to a report in The London Sun, Leo and supermodel Bridget Hall had been spotted several times "canoodling together" around NYC in 1994. Though Bridget insisted that they were "just friends" (yeah right, that's what they all say) the rumor mill generating stories of the two hooking up. Even some reports go so far as to say far as to report that she once said, "He was lousy in bed." and dumped him after finding the encounter "disappointing." Not to worry, young Leo. There are plenty more fine ladies in your future, just consider this experience practice.

Celebs Daily

Sources: People, Entertainment Tonight, The Sun, Paper Mag, US Weekly, Daily Mail Australia, Page Six, Zimbio

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