Leonardo DiCaprio Gets Older While His GFs Stay the Same

Leonardo DiCaprio is one of those A-list actors who is found in meme after hilarious meme. But for some reason, his long dating life is rarely discussed. And it might have something to do with the fact that he plans it that way. You probably already know that his dating history involves models, actresses, more models, and some singers. Almost all of them are blonde, and they are (were) very young.

Leonardo DiCaprio attends the 92nd Oscars Nominees Luncheon / Leonardo DiCaprio and Gisele Bundchen on the red carpet of the 77th Academy Awards / Anne Vyalitsyna on the red carpet / Leonardo DiCaprio and Kate Winslet attend the 88th Annual Academy Awards

Photo by Kevin Winter, Getty Images / Chris Polk, FilmMagic, Getty Images / Dimitrios Kambouris, WireImage, Getty Images / Dan MacMedan, WireImage, Getty Images

Leo seems to have a particular place where he meets his leading ladies, and it’s the Cannes Film Festival. In his late 40s, the actor goes to Cannes every year, whether or not he even has a movie to promote. It might just be because the 12-day film festival has proven to be the best place to meet and spend time with models on the very expensive yachts that surround it.

Is Leonardo DiCaprio Married?

The answer is no – not yet. But he might just pull a George Clooney and get married after decades of bachelorhood. Leo is dating someone, and she seems to be something special. Her name is Camila Morrone; she’s 23 and also 23 years younger than 46-year-old Leo.

Leonardo DiCaprio and Camila Morrone at a soccer game.

Photo by Jean Catuffe / Getty Images

Leo went to Cannes with her in 2019, and in line with his custom, he didn’t identify her as his girlfriend to the media, nor did he walk the red carpet with her at any events. We’ll talk more about their relationship later, but, for now, let’s just say that the reason Morrone might be special is that he seems to actually be interested in her. It began with the tabloids, of course…

Is She the One?

The two spent quality time in France, and thanks to The Daily Mail, they were captured interacting after a lunch date. The headline read: “Leonardo DiCaprio, 44, proves he’s the ultimate Instagram boyfriend as he takes girlfriend Camila Morrone’s, 21, photo during rare outing in Cannes.”

Leonardo DiCaprio and his girlfriend Camila Morrone attend the UEFA Champions League Group C match in Paris.

Photo by Jean Catuffe/Getty Images

After those photos hit the Internet, a wave of interest began on social media, and it made Leo look like he was really into her. Over the past two decades, the A-lister has dated tons of mostly blonde models under the age of 25. But the thing is, he hardly ever acknowledges them in the media. And he rarely shows any PDA (public display of affection). So what gives?

Bike Rides, Yachts, and Secrecy

Those who follow Leo’s life (or like to read the tabloids) probably saw him with Toni Garrn, Nina Agdal, Kelly Rohrbach, and Erin Heatherton. You might have seen him in paparazzi shots, hanging out with his photogenic flavors of the month on bicycle rides, on yachts, or at clubs. But the guy never mentions them to the press.

Leonardo DiCaprio is interviewed by multiple reporters at a movie premiere.

Photo by Dave Hogan/Getty Images

The mystery of his dating life (and the fact that he’s dated mostly models) has only made people more interested. Leo has managed to create a pretty nice situation for himself. He gets to date Victoria’s Secret and Sports Illustrated models, reaps all the benefits, and never has to explain himself when the relationships end.

The First Rule of the Dating Club

A chart of his dating history went viral not too long ago on Reddit. Anyone who saw it can see that as Leo gets older, his girlfriends stay the same age. And they all follow the first rule of Leonardo DiCaprio’s dating club: You never talk about fight club. Sorry, I mean, “you never talk about the relationship.”

A chart mapping the girls that Leonardo DiCaprio has dated.

Source: Pinterest

None of his past girlfriends has ever spoken about him in the press. So, how is it that he has managed such a careful balancing act for over two decades? Well, before we get into his dating history, it might be fun to see what the anatomy of a relationship with Leo is really like.

Single = Cannes = Models

Thanks to Vice and their “Rag Time” deep dive on Leo’s dating life. We can get a picture of what it means to be involved with the actor every girl would love to spend a weekend on a yacht with. First, when Leo’s single, he goes to Cannes to meet new models.

Leonardo DiCaprio on the red carpet during the 72nd annual Cannes Film Festival on May 22, 2019

Photo by Stephane Cardinale – Corbis/Corbis- Getty Images

And when Leo’s in a relationship, he brings the model he’s dating to a festival and meets even more models. The trend started around 2011 when Leo went to Cannes shortly after his breakup from then-25-year-old Israeli model Bar Refaeli.

Bar Refaeli: Conservation and Politics

Leo met Bar Refaeli in 2005 at a party thrown by U2 in Las Vegas. The couple apparently bonded over their love of conservation and political views. The two of them even met Israeli PM Shimon Peres in 2007 to talk about promoting peace and the environment.

Bar Refaeli and Leonardo DiCaprio front and center at a basketball game.

Photo by Noel Vasquez/Getty Images

They were together for quite some time, but after an on-again-off-again trend in their relationship, they called it quits in 2011. She was Leo’s sixth Victoria’s Secret romance. Their split was reported in Page Six: “It was amicable, they’re still friends, and they are still talking,” a source stated. “They just grew apart and went their separate ways.”

Blake Lively: Wining and Dining

After his split from Refaeli, Leo went to the festival solo and met, wined, and dined then-23-year-old Gossip Girl star Blake Lively on a yacht. Their affair was brief before she dumped him for Ryan Reynolds. But before they broke up, they were said to be quite domestic.

Blake Lively is making macarons alongside two other women.

Source: Instagram/@blakelively

According to some unnamed friends of Leo’s, “She spent the whole time baking… Leo’s never dated a girl who can cook. And he’s smitten!” But after five months of domestic and romantic bliss, it was over. An insider stated that distance and Leo’s work commitments contributed to the breakup.

Nina Agdal: Driving in the Hamptons

In 2016, Leo met Danish Sports Illustrated model Nina Agdal at that year’s Cannes festival and started dating her. He then dumped her a few days before the next Cannes festival (she had just turned 24, and his unofficial limit is 25). She caught Leo’s eye in 2014, and they reconnected again in the summer of 2016.

Model Nina Agdal on the red carpet during the 68th annual Cannes Film Festival on May 18, 2015.

Photo by Venturelli/WireImage/Getty Images

Leo spent the summer with Agdal, who is Adam Levine’s ex. The two were reportedly rear-ended while driving in the Hamptons. By May 2017, they parted ways. She was Leo’s 10th Victoria’s Secret model.

Camila Morrone: The Current Lucky One

He went to the 2017 Cannes festival solo, as did Argentinian-American model Camila Morrone, who was still a teenager at 19 years old. The pair started dating six months later and are still an item to this day. They were first seen on a shopping trip at Barney’s in L.A. in December 2017.

Camila Morrone on the red carpet during the 70th annual Cannes Film Festival at Palais des Festivals on May 24, 2017.

Photo by Kristina Nikishina/Epsilon/Getty Images

What might be the most promising sign of a possible long-term commitment was the two showing up together at the 2020 Academy Awards – something Leo simply doesn’t do. Who knows, maybe it was because he was nominated for his role in Once Upon a Time… in Hollywood.

Lockdown = The True Test

But if there’s any test that proves the relationship is steady, it’s the lockdown. The couple has passed the test with flying colors. One source told People, “Leo has spent 24/7 with Camila for months at his house.” The fact that she’s 23 years his junior isn’t an issue for them.

Camila Morrone is taking a selfie in a large mirror.

Source: Instagram/@camilamorrone

Whether or not he plans on going down on one knee is not clear at this point. He is, after all, a very private guy, so it’s not like we would be getting any announcement beforehand. Still, people have been speculating, of course, and some even say the young model is pregnant.

Down to a Science

According to Ashley Smith, one brave model who talked with Cosmo, Leo has his dating method down to a science. Smith didn’t date Leo (at least she didn’t admit it) but saw him at a party in Cannes.

Model Ashley Smith on the red carpet during the 65th Annual Cannes Film Festival at Palais des Festivals on May 20, 2012.

Photo by Venturelli/WireImage/Getty Images

She said he showed up in casual clothes and a baseball cap while everyone else was in tuxedos. She said he “was there for five minutes, found a girl, and left.” But with all this talk of Cannes, you might be thinking, well, what about the other 353 days of the year?

40 Plus? Not for Leo

In 2017, The New York Daily News reported on how Leo was handling the club scene in the wake of the MeToo movement. At a lower Manhattan Halloween party, people were in shock when Leo didn’t approach “any of the beautiful women at a 40-plus-person party that was stocked with models who appeared to be just his type.”

Leonardo DiCaprio, 45, kept a low profile in a baseball cap and black hoodie while talking to friends.

Source: Pinterest

An insider reported that he arrived with five friends, in a baseball cap, and didn’t talk to anybody outside of his group.” It’s been well documented that Leo tends to use his friends to help him land models – a tactic he’s used since he was in his 20s.

The Girlfriend Experience

After the initial Cannes/party dating scene, some lucky girls get to progress to the girlfriend stage. It appears that once the model becomes his girlfriend, she gets the full “girlfriend experience.” As seen with Morrone, he’ll take her on yachts. They’ll go snorkeling in Positano and even sit on the ground at Coachella.

Camila Morrone is sitting on the grass during a sunny day at Coachella.

Source: Pinterest

However, despite these public outings, the model turned new actress has never once discussed her relationship or posted about Leo on Instagram. And she has 1.7 million followers. It’s come to the point where journalists don’t even bother asking Leo about his personal life.

Bridget Hall: His First

According to Vice, the last time Leo earnestly spoke about “falling in love” was in an interview in 1994. He must have experienced some trauma if, after that, he swore to secrecy. So, who was in his life at that time? Well, it could be one of two women.

Leonardo DiCaprio and Bridget Hall in 1994.

Source: Pinterest

Model Bridget Hall and Leo hooked up as 20-year-olds back in 1994 in New York. Media reports were so candid about suggesting that he was her “first,” but Hall “vehemently denied” the claim. Speaking of first, Hall was Leo’s first Victoria’s Secret model.

Brittany Daniel: Sweet Valley Love

Another one of his 1994 romances was with Brittany Daniel. Remember her from Sweet Valley High? She was one of the blonde twins on the show. Daniel appeared with Leo in The Basketball Diaries; they filmed a scene where her character seduced him.

18-year-old Brittany Daniel is sitting close to Leo on-screen in The Basketball Diaries.

Source: Pinterest

At the time, she was 18, and he was 19. Their on-screen chemistry transcended into real life. For a while, at least. The two obviously broke up not too long after that. But ever since the mid-‘90s, Leo chooses not to divulge his personal life. Nowadays, when he does do press, it’s mostly about his global warming charity work (via the Leonardo DiCaprio Foundation).

Do They Sign a Non-Disclosure Agreement?

Vice states that the last time anyone directly asked Leo about his love life in the press was an interview with Parade magazine in 2016. His response was something of a “short non-answer.” There’s a rumor that’s been going around for quite some time about a non-disclosure agreement that these models allegedly sign.

Leonardo DiCaprio attends the 92nd Oscars Nominees Luncheon.

Photo by Kevin Winter/Getty Images

It’s not even a crazy rumor seeing as none of them ever give tell-all interviews or gossip about Leo to the tabloids, even after a breakup. No one has gotten their hands on this rumored NDA, but in 2017, The Los Angeles Times reported on NDAs that Leo used to have employees sign at his production company Greenhour Corp.

No “Confidential Information” Whatsoever

According to an expert, those agreements were “wildly overboard” and prevented employees from disclosing any sort of “confidential information” about the actor. And by “confidential information,” he means information about him, his family, his friends, his businesses.

Leonardo DiCaprio signs autographs for fans on the red carpet.

Photo by George Pimentel/WireImage/Getty Images

There’s also a clause that states they can’t speak of “the existence of the contractor’s business and/or personal relationship with DiCaprio,” the Times reported. In addition, the NDA provides a long list of “offensive/inappropriate material” that is also confidential information. After knowing this, it’s not so far-fetched to assume that his ladies sign something of the sort as well.

The Code of Silence

Whether or not they sign an NDA is unknown, but the women in Leo’s orbit behave in an almost mafia-styled silence. In the aforementioned Cosmo interview with Ashley Smith, another model named Lily Aldridge, who had never even dated Leo, visibly shut down when she was questioned about him.

Lily Aldridge attends the 2020 Vanity Fair Oscar Party.

Photo by Axelle/Bauer-Griffin/FilmMagic/Getty Images

Fellow model Gigi Hadid stepped into the sort-of-conversation to say that Aldridge and Leo were “friendly,” but Aldridge herself made no comment and just simply shook her head. Their sworn secrecy is a little suspicious, don’t you think? It’s basically what the Italian mafia adhere to omerta (the code of silence).

Toni Garrn: Breaking the Rules

There have been rare occasions here and there when one of Leo’s girlfriends has publicly shared information about her experiences with him (gasp). During the summer of 2013, then 38-year-old Leo was dating German model Toni Garrn.

Toni Garrn walks the runway at the Ermenegildo Zegna fashion show.

Photo by Jacopo Raule/Getty Images

He hosted her 21st birthday party at his Hollywood Hills mansion. Some of her friends tweeted and posted photos from the party on Instagram. Gossip blogger Lainey Gossip shared the photos on her site before she nearly immediately got a request to remove them. Then, in a domino effect, most of the trigger finger friends also quickly deleted them.

“With 20 Girls” in Tow

Two photos, however, remain online. There’s a group shot and a photo of Garrn’s friend posing with Leo’s dog, Django. It looked like Garrn, Leo’s ninth Victoria’s Secret model, was the real deal during their secret relationship. After all, she fit the bill.

Garrn’s Friends in a group shot outside on the couch/ Garn’s friend posing with Django, the dog.

Source: Facebook

They even lived together for a while. But despite all that, Leo broke it off with Garrn in December of 2014. After the breakup, Leo was seen leaving a Florida nightclub “with 20 girls” in tow. Leo briefly reconnected with Garnn in 2017, but by then, the model had already moved on to actor Alex Pettyfer.

Gisele Bündchen: The Famous and Powerful Ex

The only one of Leo’s exes who really talked about what it was like to date him is one of his most famous and powerful model girlfriends, Gisele Bündchen. It took 14 years for her to muster up the courage (or whatever it was) to do it.

Leonardo DiCaprio and Gisele Bundchen on the red carpet of the 77th Academy Awards.

Photo by Chris Polk/FilmMagic/Getty Images

Before Gisele was Tom Brady’s trophy wife (they married in 2009), she was Leo’s flavor of the early 2000s. The supermodel, and VS Angel number five, started an official romance with Leo in 2000. By 2004, they were one of the People’s Most Beautiful Couples. But their relationship wasn’t as pretty.

The On-Again, Off-Again “It” Couple

Gisele and Leo endured an on-again, off-again type of relationship. She finally called it quits in 2005, but before that, they were the ultimate “it” couple. The reason for their split was a lot deeper than what the tabloids will have you believe (that she was tired of waiting for him to pop the question).

Leonardo DiCaprio and Gisele Bundchen are walking their dogs.

Photo by Ronnie Taylor/FilmMagic/Getty Images

The truth is that underneath her glamorous facade, Gisele was suffering from severe emotional instability. In 2019, she told Porter that she had been suffering from panic attacks. At her lowest point, she confessed that she considered jumping off the balcony.

She Soul-Searched, but He “Stayed the Same”

Gisele stated that she broke it off with Leo after she finally decided to cut back on partying in order to cope with her anxiety. “No longer numbing myself with smoking, drinking, and too much work, I was becoming more and more aware of things that I’d chosen not to look at,” she said.

r Leonardo DiCaprio and girlfriend, model Gisele Bundchen attend a basketball game.

Photo by Vince Bucci/Getty Images

She added, “Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes.” And so, she decided to part ways with Leo and start fresh.

But They Still…

In an interview with Vanity Fair in 2009, Gisele confirmed that Leo is “a really wonderful person.” Gisele also noted that they still speak, that’s she’s still friends with his mom, and that he even still has one of her dogs. “He’s done a lot for the environment, and I admire what he’s done,” she added.

Supermodel Gisele Bundchen appears on

Photo by Kevin Winter/Getty Images

“We know what we had. We were very young, and we grew together in a lot of ways.” But according to Gisele, they were “just not meant to be boyfriend and girlfriend.”

The following are other lucky ladies who used to date the Hollywood star…

Naomi Campbell: Angel Number Two

Back in 1995, when just about every teenage girl (myself included) had a poster of Leonardo DiCaprio on their wall, he was arm in arm with supermodel Naomi Campbell. Around this time, the actor was seen flirting with her, and after a brief fling, the couple decided things would be better if they were just friends.

Leonardo DiCaprio and model Naomi Campbell pose as they attend the International Tiger Conservation Forum on November, 23. 2010.

Photo by Konstantin Zavrazhin/TCF/Getty Images

She was his second Victoria’s Secret model, and after calling it quits, the pair has remained on friendly terms over 25 years later. If you want proof, you can see the photos they’re in together these days.

Demi Moore: A Misnomer

After her public split from Bruce Willis, Demi Moore took a chance on love again. And as we know from her relationship with Ashton Kutcher, she likes ‘em young. Moore, who’s exactly 12 years older than Leo, was spotted with him on a dinner date back in 1997.

Leonardo DiCaprio and Demi Moore spotted having lunch through a window.

Source: Pinterest

But later on, neither Moore nor Leo confirmed if they ever gave it a shot. Moore is unlike the rest, as she’s neither blonde nor a model. But then again, this was still the ‘90s, before he created a trustworthy repertoire for himself in the ladies department.

Natasha Henstridge: A 1997 Fling

Another one of Leo’s past party friends was model-turned-actress Natasha Henstridge, whose big break was playing the lead in Species. Remember her? Well, the pretty pair reportedly had a fling in 1997. Henstridge wasn’t the first model Leo was linked to, but given both of their career ambitions, it’s no surprise the relationship didn’t last.

Actress Natasha Henstridge attends the Fourth Annual Vanity Fair Oscar Party on March 24, 1997.

Photo by Sam Levi / WireImage /Getty Images

Around the time the couple was introduced to one another, Leo was already on the brink of becoming a massive super star, following the release of Titanic. It was also around the time that Henstridge experienced her first taste of fame as an actor, instead of a model.

Kristen Zang: The Heart-Breaker

Before Henstridge, there was model Kristen Zang. The two were together for a couple of years, around 1996, which came after his rise to fame following the success of Romeo + Juliet. He was filming Titanic, and flew her to the set for romantic reunions.

Leonardo DiCaprio & Kristen Zang at the Mann Chinese Theatre in Los Angeles, California.

Photo by Steve Granitz/WireImage/Getty Images

He was uncharacteristically candid about his feelings about her. “I can’t wait to see her at the end of the day,” he rather cutely admitted. “She is the cutest girl in the world!” But unfortunately for him, Zang couldn’t cope with a relationship in the limelight and broke his heart by ending it.

Kelly Rohrbach: Rumors of Engagement

In 2015, the 25-year-old American model Kelly Rohrbach and Leo were spotted doing some uncharacteristic PDA as they rode bikes together in New York City (a seemingly favored pastime of his). The relationship seemed to have gotten very serious – so much so that there were rumors of them getting engaged.

Leonardo DiCaprio, Kelly Rohrbach and at the Men's Final on day fourteen of the 2015 US Open.

Photo by Jean Catuffe/GC Images/Getty Images

But, they broke up about a year later. Rohrbach has graced the page of Sports Illustrated Swimsuit Issue (it’s not just Victoria’s Secret that pulls him in). But the model is more than just a pretty face. She has a degree from Georgetown University and is an “incredible conversationalist.” The breakup was reportedly “mutual” by the way.

Helena Christensen: Angel Number Three

Leo had a “Helena Christensen” period back in 1997 after Titanic came out, but it only lasted a few months. (And yes, it seems as though he saw multiple women around the same time). Victoria’s Secret model number three showed up as Leo’s career was ramping up in the mid to late-‘90s.

Leonardo DeCaprio and Helena Christensen out at a bar in 1997.

Source: Pinterest

Christiansen may just be one of the best known Angels, too. Back in 1997, she might have been even a bigger name than Leonardo DiCaprio himself. Once the word spread that these two beauties were dating, Hollywood couldn’t wait to see what would come of the couple. In the end, nothing happened.

Bijou Phillips: A Fellow Actor

Bijou Phillips was no stranger to the spotlight before dating her superstar boyfriend Leo. That’s because she’s the daughter of The Mamas and Papas singer John Phillips. Bijou dated Leo back in 1998 when she was still just a teenager.

Bijou Phillipson the red carpet during 1998 MTV Video Music Awards.

Photo by Ron Galella, Ltd./Ron Galella Collection/Getty Images

He helped her snag a role in Black And White, after he introduced her to the director, James Toback. Things ended between the two, though, and she eventually moved on to other actors. At first, she was dating Elijah Wood. But now she’s married to That ‘70s Show alumnus Danny Masterson.

Eva Herzigova: Angel Number Four

It doesn’t take long for Leo to move on, clearly. He moved on to another model, this time Czech model Eva Herzigova. Herzigova met him at a party after the Paris premiere of The Man in the Iron Mask. The two had a two-month-long fling in 1998.

Czech supermodel and actress Eva Herzigova slays on the flood at the 1998 Cannes Film Festival.

Photo by frederic meylan/Sygma/Getty Images

After he was introduced to her at the premiere, he knew he was going to need to pursue a romantic relationship with her. But, of course, their romance was short-lived and both parties moved on. Herzigova moved on to marry Bon Jovi drummer Tico Torres. And, yes, Eva was once a Victoria’s Secret model, making her Angel number four.

Anne Vyalitsyna: Angel Number Seven

If you’ve heard of Anne Vyalitsyna’s name, it’s because she was a Victoria’s Secret model (she’s number seven on Leo’s list). You might also recognize her as Adam Levine’s ex. But before that, in 2009, the Russian model was being romanced by Leo.

Anne Vyalitsyna on the red carpet.

Photo by Dimitrios Kambouris/WireImage/Getty Images

He treated her and her friends to an Ibiza trip, where the two “couldn’t keep their hands off each other.” It came during a rough patch with Bar Refaeli, and he found himself single enough to go after the double whammy: both a Sports Illustrated and Victoria’s Secret model. Anne just didn’t realize that his heart was still with Bar at that point.

Alyce Crawford: His Australian Fling

After Blake Lively left him, Leo was rumored to have dated Australian swimwear model Alyce Crawford. She was linked to Leo in 2011, when he was in her home country filming The Great Gatsby. Crawford maintains that she and Leo never officially dated, but the two were seen together quite a lot.

Alyce Crawford attends Fashion week 2011.

Photo by El Pics/Getty Images

Several sources claimed they saw Crawford going to Leo’s hotel, but noted that the two were always very cautious about being seen together in public. Since Leo was going through a rocky romantic time, anything is possible.

Erin Heatherton: Angel Number Eight

Leo’s 8th Victoria’s Secret model came in the form of Erin Heatherton, who dated him for 10 months between 2011 and 2012. Like Alyce Crawford, Heatherton was also seen in Australia with Leo while he was filming The Great Gatsby. The pair split; sources said “it was just time to move on.”

Leo and Erin walking the streets of New York City.

Source: Pinterest

But when it comes to stars dating stars, 10 months is a long time. The pair looked promising. A source told Us Magazine that there was “no bad blood” and that “they still care about each other a lot.” But they both claimed that their schedules were simply too insane to keep the relationship going.

Paris Hilton: The Unexpected One

Not only were we shocked to discover this, but when Leo hit it off with socialite Paris Hilton in 2000, even those at the L.A. club they were in were stunned and confused. Hilton might just be that last person I would ever expect Leo to be interested in (sorry, Paris).

Paris Hilton on the red carpet, 2000.

Photo by Jeff Kravitz/FilmMagic, Inc/Getty Images

Dating a socialite isn’t in Leo’s M.O., but the two found themselves in the same social circles. They would show up to the same place at the same time – often enough that rumors began that the two of them were involved. But the bachelor and the heiress’s fling was over as quickly as it began.

Kat Torres: Quick to Blab

By 2013, Leo found another blonde bombshell to romance. Kat Torres is a Brazilian model who met Leo at, of course, Cannes. Torres fit Leo’s favored aesthetic, but it seemed there wasn’t much chemistry between them. Their relationship was very short-lived.

Kat Torres attends the TAGS Two year anniversary party on November 6, 2014

Photo by Mark Davis/TAGS/Getty Images

It didn’t help that, at the time, Leo was bouncing between Torres and another woman (most likely Toni Garrn) who had a stronger hold on his heart. Torres, who is 14 years younger than him, was quick to break the code of silence. She confirmed that she was dating The Titanic star in October 2013.

Miranda Kerr: More Than Friends?

Following the end of her marriage to Orlando Bloom, Miranda Kerr formed a friendship with Leo, but it’s not very clear whether they became more than friends. The former Victoria’s Secret model had dinner with Leo, and an eyewitness said they looked like they were having a great time.

Miranda Kerr is seen on November 28, 2012 in New York City.

Photo by David Krieger/Bauer-Griffin/GC Images/Getty Images

Leo never went public about his link to Kerr, which might be because Kerr was still officially married to Bloom. Kerr and Bloom officially announced their split in 2013, but she was out and about with Leo in 2012.

Madalina Ghenea: Another Fling in Australia

During Leo’s blue days after splitting with Bar Rafaeli, Romanian model Madalina Ghenea called herself Leo’s girlfriend in 2012, but she never broke the rules about not talking about it. “I want to be famous for the projects that I’m in and not for relationships,” she said.

Madalina Ghenea walks the red carpet at the Palais des Festivals during the 65th Cannes Film Festival.

Photo by Anthony Harvey/Getty Images

The two were seen getting all cozy together at his temporary home in Sydney when he was filming The Great Gatsby. The relationship ended soon after, though. But it wasn’t only Americans who were following the story. Romanians and Italians couldn’t get enough of the gossip.

Rihanna: Too Busy to Flirt?

After his sudden split with Kelly Rohrbach, Leo was seen with Rihanna at various events. The two hung out in Paris and canoodled at the Levi’s Brand’s Neon Carnival in April 2016. The pair met at a Playboy mansion party after the 2014 Golden Globes.

Singer Rihanna and actor Leonardo DiCaprio attend a concert.

Photo by Jesse Grant/Best Events/Getty Images

There was also word that Leo was Rihanna’s plus-one at her cousin’s wedding in Barbados in 2015. Leo and Rihanna shared a “flirtatious” night in a Paris club in early 2016. Their fling didn’t last very long. Rihanna denied anything romantic, saying she’s too busy to date anyone.

Laura Whitmore: The One in the Crowd

At the 2016 BAFTAs, Leo fancied Irish TV presenter Laura Whitmore whom he saw in the after-party crowd and was “all over her.” According to one source, he invited her back to his hotel room. Laura addressed the rumor in Hello! Magazine, telling the outlet, “Everyone was just having fun. There was a lot of dancing.”

Laura Whitmore whispering something into Leonardo DiCaprio’s ear at the BAFTA after party.

Source: Facebook

Either way, it seems like it might have been a one-night kind of thing. And that would hardly be surprising. It also might explain why she mentioned anything to the magazine – they didn’t have the chance to discuss the code of silence (I’m speculating, of course…).

Lorena Rae: One of the Few Brunettes

Model Lorena Rae shares mostly photos of herself, which is likely how she caught Leo’s eye. The couple was seen together on a lunch date in New York City before riding bikes around the city. An eyewitness said the two “seem like an item.”

Lorena Rae on the red carpet during the 72nd annual Cannes Film Festival.

Photo by Samir Hussein/WireImage/Getty Images

There was something different about the 23-year-old German model. She’s one of the very few brunettes that Leo has been seen with in recent years. Their romance began around August 2017, but while he was trying to woo her, he was still hitting the town with his ex, Toni Garrn.

Victoria Lee Robinson: Spicing It Up

Leo was seen in early May 2016 leaving Justin Bieber’s Purpose Tour after party with Victoria Lee Robinson, the 23-year-old Ford model. It’s unclear if or for how long a fling went on – if it even did. Robinson was another uncharacteristic choice as she’s brunette, but it looks like Leo likes to spice it up sometimes.

Victoria Lee Robinson posing for a candid looking shot.

Source: Pinterest

Like many of his other links around that time, what happened with Robinson amounted to not much more than just a fling. It could be because he’s a busy man, or maybe he was too hung up on an ex.

Georgia Fowler: The Racy One

Leo was spotted with 23-year-old brunette model Georgia Fowler, who is Harry Styles’s ex. The pair got close at Cannes in 2013. It surprises no one that they didn’t become an official item. It might be due to Fowler’s past.

Georgia Fowler walks the red carpet during the 71st annual Cannes Film Festival.

Photo by Dominique Charriau/WireImage/Getty Images

The brunette had tongues wagging in 2013 when she posed for a racy campaign for French Connection’s Autumn-Winter campaign. She was photographed naked and clothes were drawn over her body. The Advertising Standards Authority reportedly received plenty of complaints over the “offensive” campaign that shocked shoppers on busy streets where there were children.

Ashley Roberts: The Pussycat Doll

Leo had some fun with Pussycat Doll Ashley Roberts in 2009, but it was one of those blink-and-you’ll-miss-it moments. The actor met the singer at a Cartier International Polo event. Leo was 34 at the time and she was 27.

Ashley Roberts arrives at the 2009 Complex Premium Goods Event at MyHouse Nightclub.

Photo by Chelsea Lauren/WireImage/Getty Images

After flying to the U.K. from Madrid after having dinner with his mother on Saturday night, Leo spent the afternoon at the bash wooing Roberts. A “spy” said: “Leo came in through the back and was immediately directed towards his private table. He was swarmed by beautiful ladies, including Ashley.”

Kate Winslet: One of the Boys

Kate Winslet and Leo experienced the mania of Titanic together in 1997, which brought them incredibly close. Winslet says the secret behind their close friendship is based on the very fact that they never hooked-up. Apparently, Leo always saw her as “one of the boys.”

Leonardo DiCaprio and Kate Winslet attend the 88th Annual Academy Awards.

Photo by Dan MacMedan/WireImage/Getty Images

Leo has nothing but praise for the actress. He confessed: “I cried on her shoulder many times as we found the demands of filming under the director James Cameron so tough. We have never not been friends since that time. I speak to her all the time. But friends – not lovers.”

Kate and Leo: Friends Forever

While Leo and Kate have continued to maintain that they have never had a romantic relationship, one thing is clear: They’re very close friends. Their long-lasting friendship proves that; for the past two decades, each one has been one of the most stable presences in each other’s lives.

Kate Winslet and Leonardo DiCaprio are seen on stage holding hands during the Leonardo DiCaprio Foundation 4th Annual Saint-Tropez Gala.

Photo by Anthony Ghnassia/LDC Foundation/Getty Images

As Leo has gone from model to model, Kate has gone through three separate marriages. Their commitment to each other has never wavered. Who knows, maybe the reason their individual love lives haven’t settled yet is because they’re waiting for each other. That would be the perfect ending, wouldn’t it?

Claire Danes: On-Screen Lover, Off-Screen Hater

Speaking of costars, one of Leo’s fellow actors, Claire Danes, wasn’t so much of a fan of Leo. She was Juliet to his Romeo, so she kind of needs to be on this list. Their on-screen chemistry fooled us all, but off-screen, the actors apparently didn’t get along so well.

Leonardo DiCaprio and girlfriend Claire Danes attend the

Photo by Ron Galella, Ltd./Ron Galella Collection/Getty Images

Rumor has it that Danes found 22-year-old Leo “very immature,” and the two would even ignore each other between takes. “There was definitely a spark, but I don’t think either of us knew how to handle it. So, we sometimes sort of ignored each other. It was too big for us to really accept,” she recalled.

Irmelin DiCaprio: His Main Squeeze

There’s always going to be one lovely lady who means the most to Leo, and that’s his mom Irmelin. Leo’s parents divorced when he was a year old and he was raised mostly by his mom, with whom he lived.

Irmelin DiCaprio and Leonardo DiCaprio attend the 86th Oscars.

Photo by Jeff Vespa/WireImage/Getty Images

His German mom has regularly accompanied her son at red carpet events, including the Golden Globes and the Oscars. At the 2016 BAFTAs, Leo’s speech was about his mom when he won Best Actor for The Revenant. “One person without whom I wouldn’t be here today is my mother, and today is her birthday. I did not grow up in privilege, I grew up in a very rough neighborhood, and this person drove me three hours every day to show me a better life.”