The prodigal actor has won an Academy Award and three Golden Globe Awards over his lifetime. Leonardo is also an avid environmentalist and film producer and a professional ‘dater.’ Let us take a short look at his career and love life.
A Child Star, But Not Without Difficulties
The young actor was born on November 11, 1974, in Los Angeles, California. DiCaprio was named Leonardo after Leonardo da Vinci, perhaps forecasting that he would also be a revolutionary in his own field of work. The actor said that he originally wanted to be either a marine biologist or a child actor, and it's amazing to see that he sort of went for both with his incredible environmental activism efforts. He had a hard time finding an agent at first, and one agent even suggested that he should change his name to Lenny Williams, although we're happy he didn't.
After more than a year and a half of over 100 failed auditions, he finally managed to find his first successful acting role in the 1990's TV show "The Outsiders." DiCaprio got his big break when he starred in "Parenthood" that same year in, which got him two nominations for Best Young Actor in a Daytime Series for the show, "Santa Barbara" and Best Young Actor Starring in a New Television Series for "Parenthood." From there on, he turned into an obvious contender for many future films and paved his career to the iconic success it is today.
Unique Acting Roles
One of the most incredible things about Leonardo DiCaprio that makes him so popular as an actor is that he is never afraid to pursue a role that will demand something new from him. In fact, the actor actively looks for interesting roles that will stretch his acting abilities, as evidenced by his versatile filmography.
This is especially noticeable in an age where the majority of Hollywood films seem like boring CGI reboots. DiCaprio definitely picks to be some of the best films out there and even turns a weak story into something truly gripping.
Leo the Environmental Activist
Leonardo DiCaprio is known for his vast contributions to helping prevent climate change. These include many speaking events and even films he produced for that very same goal. In 2007, Dicaprio released The 11th Hour, a documentary film about the state of the earth's climate, which he created, produced, co-wrote, and narrated. The actor also helped create Greensburg, a TV show about the Planet Green network which shows efforts to rebuild the town of Greensburg, Kansas using sustainable energy after the May 2007 tornado.
In 2013, DiCaprio told the media that he was taking a break from acting to focus on flying around the world and "doing good for the environment." He was also the executive producer of "Cowspiracy," a controversial documentary that shows the impacts of animal agriculture on earth's climate. The actor is still very much active in his environmental efforts and often speaks at the United Nations and the rest of the world as the UN's representative on climate change.
Let’s Focus on Women
To be honest, if there’s one thing that both the fans and the media are truly obsessed with when they talk about Leonardo DiCaprio, it's his long list of romantic conquests and his never-ending chain of dates and girlfriends.
He might be an incredible actor and an inspiring environmentalist, but nothing comes close in terms of pure entertainment value than his myriad of partners. Did you know that out of the hundreds of women that the 45-year-old actor has dated, almost none of them have been over 25? He seems to have a very specific taste in women, and that’s one of the things we’ll be exploring in this list.
Most of you might know Claire Danes as Yvaine, the fallen star from the film Stardust. She's a three-time Emmy Awards winner and has also won four Golden Globe Awards, and two Screen Actors Guild Awards. Sure, today she is married with two kids to English actor Hugh Dancy, but back in the day — she had a great thing going with the young Leonardo DiCaprio. The actress was still just a teenager at the time they were dating, and rumors began to pile up while the two were on set together. There was a lot of controversy around the fact that Leo, who was 22 at the time, was dating Claire, as she was just 16. The two met while filming "Romeo + Juliet," and although Danes denies that the two were romantic, there is a lot of evidence to the contrary.
The two can be seen here at a red carpet event for "Romeo + Juliet," back when the young Leo still sported his classic boyish hairdo and back when jacket collars were still fashionable. Danes was also quite the looker and sported the then-popular fan hairstyle, which was all the rage at the time.
Naomi Campbell is one of the most prolific models in the world, after establishing herself at just fifteen years old as a leader in the modeling industry. She was one of the six models of her generation declared a "supermodel" by the industry and the press. Her recent partner was an international businessman, real estate investor, and art collector Vladislav Doronin who's known today as a billionaire and for dating the iconic model.
It's been rumored that Campbell and DiCaprio were in a fling at the time, which seems to be true based on what the many photos of the two suggest. Despite having some romantic involvement together, Campbell and DiCaprio never actually dated seriously. We have no idea how anyone can resist dating a supermodel on the level of Naomi Campbell, but we’ll give the young actor the benefit of the doubt and chalk it up to teenage foolishness.
Leonardo DiCaprio dated a whole lot of models in his few decades of acting. One example of a popular model (and actress) that he used to date is the beautiful Canadian blonde Natasha Henstridge. Although appearing in various films, Henstridge never really made her impact as an actress, as her skills seem to have centered around the modeling industry. She was married to Damian Chapa, an American actor, and also Darius Campbell-Danesh, a Scottish singer and ambassador for The Prince's Trust.
Somewhere between her two husbands, Natasha Henstridge was introduced to DiCaprio, who was on his way to massive stardom after the recent release of James Cameron's Titanic. The two began dating, and tabloids went nuts over them, although they never publicly talked about their romance, which left the media and fans with mostly speculations. We can see how the two would have made a stunning couple with their matching baby-blue eyes.
DiCaprio has dated some of the most highly acclaimed actresses and models of the time, but he also had a very varied taste when it came to the looks of his partners. Bijou Phillips is one of his most unique dates and has a career as an actress, model, and singer. She's currently married to Daniel Peter Masterson, an American actor who you might recall from That '70s Show, but dated none other than Leonardo DiCaprio many, many years before that.
Bijou Phillips’ acting career got a great start thanks to the young actor, who helped connect her with James Boback, the director of Black and White, a film that launched the young model's career. You can see in the picture just how different she was from the typical DiCaprio Girl, which might be the reason why they only lasted as a couple for a very short amount of time.
Let's face it; if there's one type of lady that you know DiCaprio is interested in, it's artistic, young, tall blonde women with beautiful faces and perfect bodies. That might be a tall order for most guys, but when you're an A-list celebrity with one of the most recognized faces in the world, it's basically your average lady. Trishelle Cannatella, one of the actor's earlier dates, became known primarily for her appearance in the reality show "The Real World: Las Vegas," where a group of diverse strangers tries to live together in Vegas.
The actress, poker player, and Playboy model disappeared from the media's attention shortly after and has not been acting in many years. She dated DiCaprio during the height of her fame when she appeared on reality shows such as "The Surreal Life," "Kill Reality," "Punk'd," and "Fear Factor." The two eventually broke up, and we're happy to say that Trishelle Cannatella then married John Hensz.
Kidada Jones was seen in the late '90s walking in shorts with her potential boyfriend, Leonardo DiCaprio. The two allegedly began dating shortly after her engagement with rapper Tupac Shakur ended due to the tragic fact that he had been gunned down and passed away. It's possible that she was just using DiCaprio as her rebound guy in order to deal with the loss of her fiance, or maybe she actually hoped that the young actor and her would begin their own true love story. Either way, eventually, the two stopped appearing together, and DiCaprio soon began his serious relationship with Gisele Bundchen.
Jones is an actress, model, and fashion designer. Unfortunately, she has not been married or engaged since her 1996 engagement to Tupac Shakur, except for a short three-year marriage to Jeffrey Nash from 2003 until 2006. It's hard to settle after dating a guy like DiCaprio, so we can definitely understand her plight. By the way, she also dated rapper LL Cool J, also known as Sam Hanna, from the popular crime show NCIS: Los Angeles.
Another short fling for Leonardo Dicaprio happened in the late '90s when he was introduced to the Czech-Italian supermodel and actress Eva Herzigová at the film premiere of The Man in the Iron Mask, an underrated action drama with Dicaprio who stars in a dual role. Their fling was a short one, something that has become expected when you see DiCaprio starting up a romance with someone. It’s unclear whether Leo is the one who usually breaks up with these models and actresses or if he’s just not marriage material. We have a hunch that it’s probably the former.
Herzigová was born in the Czech Republic and began her modeling career at age sixteen after winning a beauty contest in Prague. She was married to Tico Torres, Bon Jovi's drummer, from 1996 until a year before meeting DiCaprio. She has since gone on to have three sons and still appears in various fashion projects. The model was pictured with young Dicaprio in some pretty intimate moments when the two were together.
One of the most public relationships that Leonardo DiCaprio had ever had was with the beautiful Israeli model Bar Refaeli. The two met at a Sports Illustrated party in Las Vegas just shortly after Dicaprio and Gisele Bundchen had broken up their (relatively) long relationship. Perhaps he was somewhat saddened by the relationship's ending and was looking for another beautiful blue-eyed model to replace his previous love with. The two dated on and off from 2005 up to 2011 before officially breaking up their relationship.
Bar Refaeli is perhaps one of the most popular people to ever come from Israel. She is the most internationally successful model to ever come out of the small country and co-hosted the media frenzy that was the 2019 Eurovision which took place in Tel Aviv, Israel. She has two children and is currently married to Adi Ezra, an Israeli billionaire who made his fortune as a businessman. Despite the relationship between DiCaprio and Refaeli being a bit rocky, it was still one of the most popular pieces of news in Israeli tabloids at the time.
Dicaprio and Bar Refaeli didn't have the most stable of relationships. In the six years they had dated, the actor had found himself with various other women that ironically looked almost exactly like his then-on-again-off-again girlfriend. One of these women was Anne Vyalitsyna, a Russian American model who is best known for appearing in Sports Illustrated Swimsuit Issues from 2005 to 2014. They were often seen vacationing in glamorous locations such as Ibiza. The two were mostly a fun fling as Leo eventually returned to Bar Refaeli.
Anne Vyalitsyna was engaged to Adam Cahan, the former Senior Vice President of Yahoo!'s mobile department, but that eventually ended, as well. She has a very interesting life that includes doing marathons and volunteering to help people with disabilities. Vyalitsyna also dated Adam Levine from 2002 to 2011 and used that connection to appear in two of his band's, Maroon 5, music videos, the most popular being "Misery."
It seems that Leonardo Dicaprio has dated just about everyone in Hollywood, which means that it was bound to happen that some of his exes would eventually marry yet remain in the same Hollywoodian circles. Blake Lively, whom he dated in later years, is just one example of this as she is currently married to the very talented actor Ryan Reynolds and shares children with him. While some would consider this to be an upgrade, we wouldn't want to hurt Leo's feelings, so let's just say we're glad she found someone. Blake was a lot more motherly than most of Leo's previous girlfriends and reportedly used to make him food, something which he was very grateful for. Like anyone would turn down a home-cooked meal made by Blake Lively.
Lively is best known for her role as Serena van der Woodsen in the CW drama "Gossip Girl." She also starred in various other films but is mostly known today for being the wife of Ryan Reynolds. The couple lives with their children in Pound Ridge, New York, in Westchester County. She definitely looks like a classic match for DiCaprio with her long legs, blonde hair, and beautiful eyes. Unfortunately for Leo, part of that match also meant a fairly short-lived relationship, which is exactly what happened between the two.
One of the only cases where it really appeared like Leonardo DiCaprio might actually finally settle down with someone was during his relatively long relationship with supermodel and activist Gisele Bundchen. Leo dated the Brazilian supermodel from 2000 to 2005 until she decided to break up with him after feeling like their relationship was causing her more harm than good. She claims to have been drinking a lot at the time and doing drugs while living a shallow and depressed life.
Gisele Bündchen started her modeling career at age 14 when she was discovered by a modeling agency and went on to become one of the highest-earning models in the world. Her claim to fame as a model was becoming a Victoria's Secret Angel between 2000 and 2007.
Leonardo DiCaprio and former Victoria's Secret Angel and beauty queen Helena Christensen began dating shortly after the actor starred in his iconic "Romeo + Juliet" film. Leo was really starting his rise to fame as a Hollywood actor at the time and was actually less popular than Christensen had been. The two shared a short relationship together in 1997 that ended in just about the same manner and time frame as his other relationships. Fans and tabloids hoped that Leo and Helena would last a little longer since the two had shown quite a lot of potential together, but alas, you shouldn't keep your dating hopes high when it comes to DiCaprio.
Christensen is still modeling and has also become a businesswoman and photographer in recent years. She's also an avid climate change awareness activist, which means there's a chance she and DiCaprio might yet cross paths again someday. She has since dated Australian musician Michael Hutchence, popular actor Norman Reedus (known mostly from his role as Daryl in AMC's "The Walking Dead"), and even the Interpol singer Paul Banks for a total of seven years. Helena is also quite unique in her choice of cars, choosing to exclusively drive a Morris Minors.
Shortly after breaking up with Bar Refaeli, Leonardo Dicaprio was quickly found with a new actress and model. This time it was the Romanian beauty, Mădălina Diana Ghenea. Unlike most of his recent exes, this model was actually a natural brunette, which marked quite a different choice in his relatively non-diverse set of romantic interests. The two were seen together while DiCaprio was in Sydney filming "The Great Gatsby," a romantic drama film based on F. Scott Fitzgerald's popular novel of the same name.
Mădălina Diana Ghenea started modeling at just 15 years old as a presenter for Italian designer Gattinoni. She has modeled in various shows all across the world and was the face of the luxury brand Vanitas. The model is fluent in Romanian, Italian, and English, and has even appeared in a couple of films over the past few years.
Many rumors began to appear of a certain Australian model visiting Leonardo DiCaprio's hotel while he was working on "The Great Gatsby" in Sydney, Australia. We're talking about none other than Australian Model and personal trainer Alyce Crawford, who was often seen posing with Leonardo DiCaprio in public. Although the two were never seen doing anything romantic, it was quite clear to everyone that something was going on between them, especially in these chaotic times of the actor's romantic life.
Eventually, Crawford gushed in an interview with the Daily Mail Australia that the two were just acquaintances and never actually officially dated. According to Crawford, Leo was just: "a really lovely guy." An insider told Australia's Daily Telegraph newspaper that the two were going out for about two weeks and would often meet for hookups multiple times every week. She was quite smart in the way she managed to avoid being seen with him in public, as it helped keep everything a secret, although it would have probably helped out her career to have a few romantic pictures with the popular celeb.
It seems that DiCaprio has dated almost all of Victoria's Secret's angels at one point or another. Leo has literally dated tens of models over his career, and that's just numbering the ones we actually know about. He's also dated Erin Heatherton, another Victoria's Secret angel who worked with the women's lingerie company between 2010 and 2013. This model had had a pretty successful start to her modeling career but ended up crashing and burning just this year after a very negative downward spiral.
Erin Heatherton is a Jewish American model from Skokie, Illinois. She was discovered when vacationing in South Beach, Miami, at the young age of 17 before signing with her first agency. She and DiCaprio ended up dating for almost a year before splitting up in November 2012. Despite having a relatively successful modeling career, it seems that Heatherton didn't conduct herself financially as well as she could have because, in April 2019, she filed for bankruptcy, claiming to be more than $500,000 in debt and making less than $3,000 that year. It seems that her career didn’t really take off after Victoria’s Secret job was over, and perhaps she didn’t really find her way after it.
One of Leo's most successful former girlfriends was Miranda Kerr, a popular Australian model and owner of KORA Organics, an organic skincare company. She also wrote a self-help book called "Treasure Yourself: Power Thoughts for My Generation" (which we hope contains tips on how to be one of the top 0.1% of women in terms of beauty and also how to date Leonardo DiCaprio). The model has a very luxurious list of previous dates and even found herself marrying a billionaire. Here’s a short list of some of her romantic conquests…
After dating Adrian Camilleri, a rich broker who was sent to prison, and Jay Lyon, the lead singer of the band Tamarama, she began dating popular English actor Orlando Bloom, who you may recall as Legolas from "Lord of the Rings" and Will Turner in "Pirates of the Caribbean." The two became engaged in 2010 and got married but divorced just three years later. Kerr claims to be bisexual, although she never publicly dated any women. She did date DiCaprio somewhere in between these rich and successful guys but eventually settled on marrying billionaire co-founder of Snapchat, Evan Spiegel. The two have three children and live in Brentwood, Los Angeles.
After his relationship with Brazilian supermodel Gisele Bündchen ended in 2013, Dicaprio dated Kat Torres, another Brazilian model who was more than happy to share details about their romance with the world. Torres became a model when she was just seven years old and turned it into her full-time career at age 14. She's an avid supporter of animal rights and environmental protection and donates much of her income to organizations such as the WWF, Greenpeace, PETA, Care2, and ASPCA. She currently lives in Los Angeles and considers herself a businesswoman, writer, entrepreneur, and philanthropist.
Kat Torres offers life coaching at affordable rates on her website, where you can presumably ask Torres about her short-lived romance with DiCaprio. Kat also has her own YouTube channel with over 350,000 subscribers, where she has shared many self-help tips and vlogs in her native language. She looks like she has a very interesting and successful career ahead of her, although her potential for a future with Leonardo DiCaprio is appearing slimmer by the day.
When you date a lot of women, especially those who come from the glamorized entertainment industry of Hollywood acting and modeling, you're bound to stumble on some wacky women. Alesia Riabenkova may not be crazy, but she certainly has a lot of drama surrounding her. This ex of Leonardo Dicaprio was also the girlfriend of Gerard Butler at one time.
Alesia Riabenkova has been involved in some controversy over the years. It's a good thing DiCaprio dated her before allegations ever emerged, as he has been quite clear of any controversy despite dating so many women. The Latvian-born model will probably not see a lot of work from Hollywood in the coming years, mostly because fashion companies tend to stay away from women who are considered "troubled." It’s not a surprise then that the DiCaprio-Riabenkova relationship was nothing but a short blip on the iconic actor’s romantic resume.
Right after his problematic relationship with Alesia Riabenkova, DiCaprio moved on to date Toni Garrn, the German-born Calvin Klein model, Hollywood actress, and self-titled humanitarian. Garrn worked with both Calvin Klein and Victoria's Secret and even acted in a couple of films. She became an ambassador for Plan International's global "Because I am a Girl" campaign, whose goal is to help eliminate gender inequality worldwide. She also founded the Toni Garrn Foundation, which seeks to help women's rights and advocate for gender equality.
DiCaprio and Garrn dated on and off through 2013 and 2014. Perhaps this was the actor's way of filling the void left by his former girlfriend, Bar Refaeli, who happens to look very similar to Garrn. Leo and Toni didn't quite manage to make things stick and left the on-and-off relationship, which lasted for about a year. In a stunning turn of events, Leo was seen in 2017 walking hand in hand again with Garrn, as the two presumably got back together for a short time before splitting up again. You can really tell the look of pride on Toni Garrn's face as she took the bachelor out for a walk. She was grinning from side to side while he held his head down in shame. The model has over 1.5 million Instagram followers, and it seems her modeling career will only get better for her from now on.
Katie Cleary considers herself a model, actress, philanthropist, and filmmaker, and spends much of her time helping improve animal welfare. It seems that the philanthropist part might not be so accurate, as it literally means "lover of people." Apparently, the celebrity was caught getting herself all nice and cozy with Leonardo DiCaprio at the Cannes 2014 festival while she was still married to her then-husband, Andrew Stern. It has been rumored that she also had some fun with "Entourage" star Adrian Grenier at that same event. This and probably many other events resulted in her husband, Stern, committing suicide mere weeks after the event.
Cleary ended up receiving exactly nothing in inheritance from her husband's estate, which all went to her late husband's parents. Katie runs an animal charity, and the two (Leo and Katie) probably got together over their shared passion for the environment and animal rights. Still, perhaps it would have been better to also think of the rights and needs of those closest to her. After the whole tragedy had run its course, the actress continued her life as usual and is currently working as a Netflix producer. Clearly also founded World Animals News, a website that shares all the latest in animal updates worldwide.
Young Demi Moore was considered one of the hotties of Hollywood back in the '80s and married stars such as Freddy Moore, Bruce Willis, and even Ashton Kutcher. All of the successful actresses' marriages dissolved after 3 to 6 years, and DiCaprio just happened to be somewhere in between Willis and Kutcher. The then-young actor met with Demi Moore for a few late-night dates, and in a picture that looks like something from a movie scene (it was captured just after the actress finished filming “G.I. Jane” where she shaved her hair), DiCaprio was clearly looking a bit uncomfortable and perhaps even in pain, as he wasn't used to dating women older than him, especially those without long blonde hair.
This cougar didn't manage to catch DiCaprio, and the two dissolved about as quickly as the foams in their late-night lattes. Moore was considered quite a big-time actress in the '80s and '90s and went on to break many records, including being the highest-paid actress in history when she received $12.5 million for her role in the 1996 black comedy "Striptease." She then acted in various films, including "G.I. Jane," "Charlie's Angels: Full Throttle," "Margin Call," and many more, although nothing managed to top her fame from the '90s, which was certainly her best decade. Since then, the actress has focused much of her time on supporting charities and doing work to promote animal rights, and attempting to disrupt child trafficking.
It's been believed that Leonardo DiCaprio had a thing going with Rihanna for a long time. The two were often seen together at clubs, and rumors were starting to emerge that perhaps something was happening behind the scenes. Skeptics thought there was likely too much divide between the two, as they came from very different backgrounds, and Rihanna, being the extremely dominant and power-savvy woman she was, lacked a certain kind of "passiveness" that is often associated with the models and actresses DiCaprio usually dates. After a while, the press discovered that indeed, the two were not dating. Instead, they found out that Rihanna had been linked to one of Leonardo's friends and not the actor himself.
Rihanna dated Drake on and off from 2009 until 2016, although she was also involved at the time with Chris Brown. She welcomed her first child in 2022 with her partner, rapper A$AP Rocky.
It wasn't really a big surprise when fans of Leonardo DiCaprio and Kelly Rohrbach found out that the two lovebirds had split up. They started dating while in New York and were often seen holding hands and smooching in public, but their tight work schedules meant that they were spending too much time apart. In Hollywood terms, this probably just meant that there were too many beautiful people around to be in a long-distance relationship. DiCaprio and Rohrbach claim that their breakup was mutual, and sources have also stated that they are still on good terms as friends and did not break up due to any third party.
DiCaprio certainly didn't wait to start partying with hotties again, though, as told by a source who said to People Magazine: "Leo partied with blondes and brunettes and male buddies including Leo's longtime friend Lukas Haas." It was about the same time that Rohrbach was slated to start filming the new Baywatch film with Dwayne 'The Rock'' Johnson and Zac Efron, so we think she was in good hands during her new state of singlehood. The tagline for the new Baywatch movie was “Beaches Ain’t Ready,” which is what DiCaprio probably says to himself anytime he breaks up with one of his token model girlfriends.
Fans of the actor were surprised when they found out that DiCaprio was dating Laura Whitmore, the Irish broadcaster who was the face of MTV Europe. The two allegedly met for the first time at an awards show as DiCaprio began to court the blonde. Although she didn't flat-out admit their romance, it was pretty clear to anyone looking that something was going on between Leo and Laura as the two started appearing more and more together.
When reporters asked the Irish broadcaster about her potential romance with DiCaprio, she responded in her best non-answer and said: “Everyone was just having fun—there was a lot of dancing.” Unfortunately, the two didn't exactly fit well together, and the whole ordeal became a short fling. Meanwhile, Laura continues to host various shows and events, from the popular British reality show "Survival of the Fittest" to the 11th Irish Film & Television Awards.
Nina Agdal was seen hanging around with Leonardo DiCaprio multiple times a few years ago, and the two were presumed to be dating. Agdal denied the rumors and claimed they were friends. After all, DiCaprio certainly has a lot of blonde, tall model friends. Like many of his girlfriends, the model was just 21 years old at the time, although that wasn't a problem for Leo, who mainly dates in the 21 to 25 years of age zone, even in his forties.
Nina Agdal is a Danish Sports Illustrated Swimsuit Model and appeared with the beautiful Chrissy Teigen and Lily Aldridge on the magazine's 50th-anniversary cover. She was originally discovered by an agent while walking the street and began her modeling career at age 18, for what shaped up to be the start of an incredibly fruitful modeling career. The young Danish model is currently 27 years old, and based on her Instagram, which has almost 2 million followers, it appears that she has a very productive modeling career ahead of her. She recently signed with IMG Models and will hopefully start showing up in magazines again soon.
When you get spotted dating models who claim to be your friends over and over again, something must be up. That's exactly why tabloids suspected that Leonardo DiCaprio was fooling around with Roxy Horner, as the two were seen hanging out together a little too often during a time when one of Leo's relationships was falling apart. Horner obviously denied all the rumors and claimed that the two were just friends, but as we've mentioned, that story loses a lot of its credibility when all your friends happen to be beautiful female models.
Roxy Horner is one more model that has allegedly dated the prolific movie star. She is based in London and works for brands such as Little Mistress, Face Gym, Boohoo, Boux Avenue, Soft Paris Superdry, and Quiz.
When it comes to dating, sometimes DiCaprio likes to go below his usual 20 to 25-year-old dating pool and steps into the sub-20s. He had a fling some years ago with supermodel Chelsey Weimar who was just 19 years old at the time. Like most of his dates, she met all of the required checkboxes: she was (and still is) beautiful, tall, a model, famous, and of course, has a pair of beautiful eyes. The two were seen leaving Nobu Malibu together, and Weimar also uploaded an Instagram photo that was allegedly taken at the actor's house.
The Dutch model once again denied the rumors, like many others before her. She is currently signed with a modeling agency called Supreme Management, and it looks like she's set to have quite a bright future ahead in modeling. This romance didn’t last more than a few weeks, just like almost every other fling that DiCaprio has had since he first rose to fame. It looks like the 45-year-old actor isn’t planning on settling down anytime soon.
After DiCaprio split up with model Nina Agdal, he was looking for a new partner to spend his nights with. The actor found that partner in another model, Ella Ross. The two were spotted in a celebrity hotspot called Venue while the star was hanging out with his longtime friend Tobey Maguire. According to a source, DiCaprio and Ross were seen "talking and dancing together for a while," the source said, “It looked rather cozy, and they seemed pretty interested in each other.”
Ross was just coming out of a relationship with reality star Scott Disick when she was spotted getting jiggy with Leonardo DiCaprio on the dance floor. This just goes to show that according to the dramatic affairs in which DiCaprio often finds himself, he's obviously not afraid of a little competition.
Leonardo DiCaprio also had a fling with the then-23-year-old Victoria Lee Robinson while he was 41 years old. That's almost twice her age! The two were seen leaving a party together at Justin Bieber's place in the Spring of 2016, which raises the question — what was DiCaprio doing at a Justin Bieber party!?
All jokes aside, the two were starting to look like a hot item together, but as luck would have it, the inevitable came, and their fling was over within a few short weeks. Victoria Lee Robinson is a fairly unknown model from Los Angeles. She has an Instagram following of just over 150,000 followers and works for Chic Model Management.
Leonardo DiCaprio was seen walking the New York streets with the then 23-year-old German model Lorena Rae. This beauty was somewhat of a departure from his usual list of blondes, but not so different. In fact, the differences end with her being a brunette. They apparently started dating somewhere around August 2017, but the romance didn't last long. Leo was also seen wooing his ex-girlfriend, Toni Garrn, who's also a model of German descent. It's no wonder that his relationships don't last for more than a few weeks — because when you're Leonardo DiCaprio, why settle for one model when you can go for two?
Lorena Rae was born in Diepholz, Germany, and learned to speak English by watching American TV shows like "Gossip Girl" (starring Leo's other flame - Blake Lively). She began modeling in her twenties and has since worked for various agencies, including The Lions, Boss Models, Unique Models, PMA, and Dulcedo Management. Her most famous act to date was walking in the Victoria's Secret Fashion Show in 2018.
One of the more interesting love interests that DiCaprio has dated over the years was model and actress Kristen Zang. At the time, he was just 23 years old and still new to Hollywood, as the actor was yet to find his rise to fame through Titanic. He invited her to his premiere of "Romeo + Juliet" and looked truly happy to be with her. Unfortunately, Zang is known as one of the only women alive who didn't want Leo and reportedly broke up with him due to his immaturity, telling him that he needed to “grow up.” Leonardo clearly didn’t take that advice seriously, at least not when it comes to dating, and some speculate that she is one of the main reasons that the actor has stayed a bachelor, dating blonde actresses and models for all these years.
Perhaps if she had stayed with him, there would still be hope when it came to locking this party boy down. Nowadays, the actor never looks this happy on dates, as you rarely even see his teeth in a smile when he's out on one of his dates. The two looked truly happy together, and that only leaves you wondering — what would their lives look like right now if this 15-month relationship had actually stood the test of time?
Another one of the superstar's young romances occurred when he was just twenty years old. Bridget Hall was apparently the first model that DiCaprio has ever dated, which means that she might be the one who gave him his original appetite for Victoria's Secret models like her. This beautiful blonde was seen attending an event with the young and upcoming DiCaprio, back when he still had his childhood innocence and quirky-happy look. The two attended several events together in 1994 and always looked extremely happy and like they had a really good thing going.
Hall's modeling agency denied any relationship between the two, which, based on the pictures, looks like a complete fabrication.
It seems that while Dicaprio is getting older, the girls he is dating keep getting younger. At this point, it looks like the only thing stopping the actor from dating 18, 17, and 16-year-old models are statutory limits. Leo was recently spotted enjoying a great time with teenage New Zealand model Juliette Perkins. The model was signed with IMG at age 15 and has been a prominent model there since. While models usually turn into Victoria's Secret models and then begin dating DiCaprio, this one decided to go the opposite way and started by dating the "Titanic" star. The two were also seen clubbing together in several venues, even though she's currently under the legal drinking age in the United States.
The young model has almost thousands of followers on Instagram and a YouTube channel with various vlogs and makeup tutorials.
One of Leonardo DiCaprio's first films that helped set up the launching of his career was Scott Kalvert's biographical crime drama film "The Basketball Diaries." It tells the true story of a promising high school basketball player who turns into a heroin addict. Despite not making a lot of money at the box office, "The Basketball Diaries" was fairly well-reviewed.
Twin sisters and actresses Brittany Daniel and Cynthia Daniel played together in the film as Blinkie and Winkie, respectively, and that's how Brittanny met the young DiCaprio. The two were apparently involved and had a fling together. This makes sense, seeing how Brittanny perfectly fits the actors' regular lineup of women. Brittanny is best known for her role as Jessica Wakefield in the 1990s syndicated teen drama "Sweet Valley High" and her portrayal of Kelly Pitts on the CW/BET comedy-drama series "The Game."
If there's one woman who clearly needs no introduction in this list, it's Paris Hilton. This social starlet and child to the Hilton family, who owns the famous hotel chains, is the only person on this list that became famous and super successful through family affiliation, way before any talent or skill was thrown into the mix. While she's not exactly the regular type of girl that Leonardo DiCaprio usually goes for, the two were often seen together back in 2000, and rumors began to rise that they were involved in some way. Either way, this romance didn't last long either because DiCaprio had already tasted the forbidden fruit of Victoria's Secret models at that point, which meant that no rich socialite was going to saturate his appetite for models.
Paris Hilton is also one of the richest people on this list, with much of her income coming from her wealth of connections in the business and entertainment industries. She often gets paid tens of thousands of dollars (and even more) just to appear in various popular nightclub venues and events. She also likes to DJ in her free time and owns her very own fashion line.
Leo began dating Camila Morrone when the young Argentine model and actress was just 22 years old. When Morrone was asked what his thoughts were about her age gap with the iconic actor, she said: “I just think anyone should be able to date who they want to date.” Of course, this opinion stops making sense if the age gap was just a bit larger, as there's still an important weight to age in a relationship.
It appears that DiCaprio prefers to date beautiful models without caring too much about maturity, which might explain why he keeps hooking in young and impressionable models that are younger than he was more than two decades ago. The two are very public about dating each other and their mutual love, but the age difference is rather startling when you notice that she could easily pass as his daughter when you look at a picture of them holding hands.
One of the more known friendships in Hollywood is that of Leonardo DiCaprio and Kate Winslet. The eternal bachelor and the British actress both got a huge boost to their careers when they starred in James Cameron's Titanic as the eternally romantic and tragic couple of Jack Dawson and Rose DeWitt Bukater.
The two claim to be good friends and have excellent chemistry together, although they claim to have never dated each other. Winslet often talks in interviews about their friendship but claims that this is one of those rare cases where romance just never really developed. It seems that the two might just be the perfect couple for each other, as both of them are single, of the same age, and have almost parallel life experiences. We can only cross our fingers and hope to one day see a relationship between the two because it seems that this might just be the perfect one for the two beautiful stars.
Back in 1998, Leo was browsing through a magazine one day and came across Amber’s gorgeous face. So, he called up his people and asked them to contact her agent, so they could meet. Soon, they went on a date and started a whirlwind fling that lasted a few months.
Amber Valetta started modeling at a young age, landing her first Vogue cover when she was barely 18 years old. She went on to grace American Vogue’s cover sixteen more times, not to mention her countless gigs as the face of Prada, Gucci, Versace, Armani, Chanel, Valentino, and Louis Vuitton.
Although this was a short fling, it's still worth mentioning because it had everybody wondering back in the 90s. It turns out that Leo DiCaprio and the stunningly beautiful Liv Tyler were supposed to co-star in a movie. Leo and Liv met at a party. Those party photos of the pair had everyone conjuring up wild theories, imagining what DiCaprio would think of becoming Steven Tyler’s son-in-law.
Ultimately, Liv Tyler went on to marry Royston Langdon, with whom she had a son, and then got together with David Gardner, with whom she has two children.
It seems that DiCaprio was as smitten as we were with his French co-star in "The Beach." Even though the movie was not a commercial success by any means, it was worth it just to see the chemistry between actress Virginie LeDoyen and Leo on screen.
It seems that chemistry translated off the screen when the two were reportedly seen together on several occasions during the filming and after the movie wrapped up. The romance was brief, and LeDoyen went on to marry three times and have three lovely children.
It was about time that Leonardo DiCaprio started a thing with a Hadid sister. He had to at some point. It seems that right after breaking up with his longtime girlfriend Camila Morrone in August 2022, Leo started pursuing supermodel Gigi Hadid.
By September 2022, it was confirmed that Leo and Gigi were officially dating. Reportedly, Gigi and Leo keep it casual since Gigi doesn’t want anything serious after her breakup with her ex-husband and the father of her child, Zayn Malik.
Another model on DiCaprio’s seemingly endless dating list is the New Zealand-born model Georgia Fowler. While attending the Cannes Film Festival in 2016 to promote his film, "The Revenant," DiCaprio and his friend Tobey Maguire went out to a hot nightclub and partied with Georgia Fowler and some of her friends.
Photos of the party showed Leo and Georgia dancing pretty close and getting extremely cozy with each other. Apparently, the fling lasted a few more weeks after Cannes and then fizzled out. This was right after the Victoria's Secret model had broken up with pop star Harry Styles.
In the spring of 2016, DiCaprio was spotted riding bikes with Polish model Ela Kawalec. Then other paparazzi pics of the couple from a few days before surfaced — the pair were having dinner at a fancy NYC restaurant.
Another set of photos included Ela and Leo partying at the Marquee nightclub, and witnesses say the two were dancing and talking as if they were a couple. DiCaprio and the 21-year-old model went out a few more times, and then Leo left for Cannes to promote "The Revenant," and the rest was history.
In 2017, American model Elizabeth Turner had a short and secret fling with the "Titanic" actor, which was made public after they were seen on a luxurious yacht in St. Tropez. The entourage included several other models and longtime friend Tobey Maguire. Then, DiCaprio and Turner were photographed a few weeks later at the beach in Malibu.
It seems they dated for a few solid months, and then Leo moved on to greener pastures. Elizabeth went on to get a Bachelor of Science from Duke University and grace the covers of Maxim, Sports Illustrated, and more.
While filming "The Great Gatsby" in 2012, Leo found himself in Sydney, hanging out at one of his favorite clubs at Kings Cross Beach. Amongst the many gorgeous models present was Australian Simone Holtznagel. The two were seen leaving the club together and then spotted some weeks later hanging out.
Reportedly, they had a very fiery romance that lasted as long as Leo was shooting for the film in Australia. Simone is known for appearing on "Australia’s Next Top Model" and being the face of campaigns for Playboy, Guess, Honey Birdette, and more.
Now, this is a noteworthy one: it seems DiCaprio’s very elite list of women includes a Spice Girl! Back in 1997, Leo had a big crush on Emma Bunton (a.k.a. Baby Spice), which isn’t surprising at all, considering the man obviously has a preference for blondes.
Bunton was barely 20 years old and at the height of her career, while Leo was enjoying his worldwide fame for "Titanic." According to mutual friends, the Spice Girl and the Titanic boy dated for a few weeks and then called it quits.
One of Leonardo Dicaprio’s breakout (and most brilliant) roles came when he played Arnie Grape in the 1993 film, "What’s Eating Gilbert Grape?" And it seems the star had a great time while filming, as he began dating his co-star, Juliette Lewis. Lewis had recently broken things off with Brad Pitt and decided to try out another world-famous hunk.
The romance lasted a short time, but the actors remain friends to this day. Juliette Lewis has had a very successful acting ad music career, starring in several films like "Natural Born Killers," "Old School," and "Starsky & Hutch."
Even a playboy like DiCaprio has had a first love and a broken heart, and for this Hollywood heartthrob, the culprit was Cecilia Garcia. They met when they were 15 years old, at a school in Los Angeles, and as per Leo’s own account, they were “totally in love.”
After a few dates, Garcia apparently dumped him because she didn’t feel there was a connection, and she didn’t like that first kiss Leo planted on her! She went on to date another classmate, which didn’t make Leo very happy, but clearly, he moved on.
This was another rare instance when Leo dated a brunette. But yes, she was still a model. In November 2015, DiCaprio and American model Cassie Amato had a fiery romance that turned into a short relationship. However, she too became another ex-girlfriend on a very long list.
But don’t be sorry for Amato, as she went on to find true love in "Hunger Games" star Sam Claflin. The two seem to be crazy in love and very happy, judging by their Insta pics.
Bryana Holly is known for being a model, Playboy playmate, and Brody Jenner’s (Caitlyn Jenner’s son) ex-girlfriend. She is your typical blonde bombshell, which means that DiCaprio couldn’t keep his eyes off her. Back in 2014, she was spotted getting into a car with DiCaprio after a night of partying.
The two were photographed during the following weeks in different scenarios – eating, walking, kissing, and partying. But as quickly as the fling started, it ended. Nowadays, Bryana is in a loving relationship with famous actor Nicholas Hoult, which started in 2017.
In one of his infamous St. Tropez yacht parties in 2022, DiCaprio was spotted getting friendly with Ukranian model Maria Bregova. Maria was interviewed on an Australian radio show, but she didn't let any details slip about what may or may not have gone down with the actor.
Maria is no stranger to age-gap relationships; her ex-husband, property and fashion mogul Ahmed Masoud Abdelhafid, is 8 years her senior.
You might remember Sara Foster as Jen Clark from the hit 90s series "Beverly Hills 90210" and the movie "The Big Bounce." Yes, she was the stunning blonde with green eyes that was also a fashion model.
It seems that in 2002, in one of DiCaprio’s breaks from model Gisele Bundchen, he had a brief romance with Sara Foster. In 2010, Sara Foster married professional German tennis player Tommy Haas and welcomed two gorgeous daughters some years later.
The 2010s were a whirlwind of alcohol, substances, parties, love affairs, and jail time for actress Lindsay Lohan. On one of those hazy party nights in 2011, her path crossed with Leonardo DiCaprio. She saw him at the nightclub, approached the star, and started dancing with him.
DiCaprio had recently broken up with girlfriend Bar Refaeli and was probably just looking for a good time. Mutual friends say the pair dated for some time, and while Lohan was pretty hung up on Leo, describing him “as the perfect man,” it seems the 12-year age gap didn’t bother him one bit.
Kendra Jade met Leo at a party back in 2002 when he was filming "Catch Me If You Can." After meeting one night, Leo and Kendra dated for a few weeks and had a very fiery love affair.
Apart from adult film entertainment, Kendra has appeared on VH1 reality TV shows like "Sober House" and "Sex Rehab with Dr. Drew" and was a recurring guest on the "Howard Stern Show" back in the 90s. She’s also famous for working as an exotic dancer and being a rock band groupie. In fact, she married Canadian rock singer Lukas Rossi in 2007.
No ultra-hot babe list is complete without the jaw-droppingly gorgeous Carmen Electra. DiCaprio met Electra back in 2000, when she was a hot 28-year-old, four years after landing the cover of Playboy Magazine. The romance was very short-lived, and many believe was for pure show.
DiCaprio was often seen making an entrance at parties by arriving with Electra and making out very publicly so everyone would see. Electra went on to land roles in the "Scary Movie" franchise, "Baywatch," "Epic Movie," and more. She’s also known for having been married to legendary basketballer Dennis Rodman, and rockstar Dave Navarro.
Leonardo DiCaprio met Danish model and actress Linnea Dietrichson at a party in the Hanover Grand nightclub in 1997. He took her home, and the couple had a very short fling that lasted around two weeks.
Leo moved on to more Latin pastures, pursuing Cuban model Carla Paneka, and Linnea went on with her career. Linnea has walked fashion runways around the world and landed a movie gig in 2015 in the short horror film "Selfie."
For once in his life, Leo DiCaprio was the younger one in a relationship when blonde babe Bobbie Brown hypnotized the 19-year-old DiCaprio. In 1993, Brown was 26 and had become wildly popular after appearing in glam metal band Warrant’s ‘Cherry Pie’ video three years before.
It wasn’t until years later, in her memoir book about all the rockers and artists she’d been with, that Bobbie Brown confessed to having seduced young Leo one night and taken him home. However, she called things off after the one-night stand, stating she felt uncomfortable that he was seven years younger than her.
A year after his major success in "What’s Eating Gilbert Grape?", Leonardo DiCaprio started attending A-list celebrity events and rubbing elbows with Hollywood’s elite. In one of these events, in 1994, he met supermodel Kate Moss, and they started dating. Even though his relationship with the British model lasted for only a few months, the two remain close friends.
Kate Moss is a world-renowned supermodel that rose to fame in the early 90s during the ‘heroin chic’ fashion era. Her modeling with Calvin Klein catapulted her to work with some of fashion’s biggest publications and brands in her decades-long career.
In 1993, 19-year-old Leonardo DiCaprio had a brief encounter and subsequent fling with "Boogie Nights" star Heather Graham. The actress was still a pretty unknown name in Hollywood back then, even though she’d acted in films like "Drugstore Cowboy" and "License to Drive."
The 23-year-old actress bumped into Leo at a party and hit it off, but not enough to have an actual relationship. Heather Graham has starred in box-office hits like "Boogie Nights," "Austin Powers," "The Hangover," "Swingers," "From Hell," and more.
Back in December 2016, while dating model Nina Agdal, it seems Leonardo DiCaprio got cozy with somebody else. Reportedly, just before Christmas of that year, Leo was seen with Florida-born lingerie model Paige Watkins. The two seemed to be partying at the same nightclubs and with the same people for a couple of weeks, even taking several smoke breaks together outside the clubs.
It was all rumors until the paparazzi spotted Leo and Paige at the famous 1OAK club, where they looked quite hot on each other. A week later, Leo went back to Agdal as if nothing had happened.
Even though the rumors were never confirmed, the photos spoke for themselves. Back in May 2017, DiCaprio and supermodel Bella Hadid were seen together at a charity gala that took place during the Cannes Film Festival. Leo had recently broken up with model Nina Agdal and was probably feeling quite lonely. Enter the stunning Bella.
Although a mutual friend said that they were just friends and “Leo is just a flirt with everybody,” we highly doubt that nothing ever happened on those lonely nights at Cannes. We guess we'll never know...
While he was filming for Tarantino’s "Once Upon a Time…in Hollywood," Leonardo DiCaprio had a brief romance with the stunning Hungarian model Barbara Palvin. Sticking to his maximum dating age, Palvin was 25 years old at the time, but she’d already made waves back in 2016 by landing her first Sports Illustrated Swimsuit Issue. That was enough for Leo.
Palvin dated DiCaprio for a few weeks before calling it off. Apparently, Leo was only interested in an open relationship. Palvin was named a Victoria’s Secret Angel and an Armani Beauty ambassador in 2019.
In July 2009, DiCaprio and model ex-girlfriend Bar Refaeli decided to take a break. Of course, Leo didn’t waste any time when it came to dating other women. One of these was British model Emma Miller. The fling ended as quickly as it had started, and Leo went back to Refaeli.
London-born model Emma went on to appear on the popular reality TV show "Made in Chelsea." She’s also modeled for Avon, L’Oreal, and Diane Von Furstenberg, and has a fashion blog with quite a following.
After splitting up with girlfriend Bar Refaeli, DiCaprio was on the prowl once again. So, in August 2009 he attended the Cartier International Polo Day, probably intending to actually watch the horses and have a nice day outside. However, his attention seemed to have been entirely on blonde babe Ashley Roberts.
Ashley, an American singer and dancer famous for being part of the pop group The Pussycat Dolls, was smitten with Leo. After making eyes at each other throughout the event, they went out and partied until 3 AM. The two dated for a few days after that, and sayonara Pussycat Doll.
The stunning American-British actress Sienna Miller couldn’t avoid DiCaprio’s charm either. In 2006, Sienna spent a lot of time in NYC while filming "Factory Girl," and she also spent a lot of time going out with Leo, just as friends first. Then, in January 2007, Miller finally dumped her husband, Jude Law, and started dating DiCaprio.
Apparently, DiCaprio had been previously dumped by model Gisele Bundchen precisely because she was furious about his flirting with Sienna. Guess it all worked out, at least for a short while.
You might remember the super sexy babe from the 2006 movie "Cashback," and if you don’t, it might be time to look up Natalie Denning. This gorgeous blonde was featured in "Strutter," "The Price is Right," and "Footballers’ Wives." But she might have given her best performance back in 2003 when she met DiCaprio at a nightclub in Paris.
She was there for modeling work, and one night while out partying, Leo called her and her friend over and ordered non-stop champagne. Denning says the party continued to his hotel, and the two kept a fling going for several days.
Before marrying into the infamous Trump family in 2005, when she tied the knot with Donald Trump Jr., Vanessa was a successful model. But, undeniably, her fame came with becoming a Trump, at least until the couple got divorced in 2018. Before she was a Trump, however, Vanessa had a brief fling with Leo DiCaprio back in 1998.
They were seen leaving a premiere party together and reportedly kept seeing each other for the weeks that followed. Clearly, nothing more ever happened, and Vanessa went on to marry and have five children.
The "Clueless" star also had a thing with DiCaprio in 1997. He was dating Kristen Zang, but his eye wandered over to a gorgeous, young Alicia Silverstone. Once Leo and Zang were over, he asked Silverstone out, and they dated for a short time.
Not surprisingly, the couple didn’t last long, seeing as they were both in the prime of their career, Silverstone right after her role in "Batman & Robin" and Leo filming for "Titanic." DiCaprio’s career skyrocketed, while Silverstone’s lasted for a few more years and then fizzled out in a string of mediocre B-movies.
Caitlin Keats is a beautiful NY-born actress that has starred in several films, like "Kill Bill: Vol 2," "Somewhere," and "She Loves Me Not." But she’s also known for dating DiCaprio in 1995 when she was 23 and Leo was 21. The two met at a wild 90s party and really hit it off. They were seen and photographed together enjoying NYC for a few weeks, eating out, kissing in public, attending more parties, grocery shopping, etc.
But as Leo’s flings normally do, it fizzled out. Nowadays, Caitlin Keats is the mother to musician Paolo Keats.
Another supermodel on Leo’s list is Canadian beauty, Shalom Harlow. The beloved 90s era, when everybody was young and beautiful and merely at the start of a wild ride in Hollywood. In 1995, Harlow and DiCaprio met at one of those infamous parties that were so good nobody remembers anything. Thankfully, there are polaroids.
The model and the actor had a romance for a week or so, and then casually moved on to see other people. Shalom Harlow was listed by Forbes in 2007 to be one of the world’s top-earning supermodels.
Ukrainian fashion model and businesswoman Alina Baikova is another model on DiCaprio’s list. Back in 2017, a lot of photos surfaced of Baikova and DiCaprio walking the streets of New York, having lunch, dinners, etc.
Even though Baikova ultimately denied the rumors of them having a fling, presumably because she would never date a close friend’s ex (in this case, Toni Garrn), we find it hard to believe that Leo was around a young, blonde model for over two days, and nothing happened.
DiCaprio has even meddled with the music world, adding world-renowned pop stars to his infinite list of women. But this is no ordinary woman; we’re talking about Christina Aguilera, the diva nicknamed ‘The Voice of a Generation’. DiCaprio and Christina were seen kissing very passionately after the premiere of "Catch Me if You Can" in 2003.
People said they looked as if they were in love. Obviously, things didn’t last, but Leo went on to become a Hollywood celebrity and Christina one of the world’s most famous singers, so it’s all good.
Brunette stunner Kendal Schuler made headlines in 2011 when she started dating DiCaprio right after he’d broken up with Blake Lively. The Australian model met Leo in Los Angeles, but it wasn’t until later that year that they met up in Sydney’s King Cross Beach and started dating.
Schuler is a mother to a cute little boy named Ryker and was recently dating copywriter Zander Williment. She has a successful career as a model, working for some of Australia’s most famous fashion brands.
It was already feeling weird not to see any Kardashians on this list. Well, technically, she’s a Jenner, but it’s all the same. As the story goes, Kendall and Leo were seen in December of 2019 getting overly close to each other. Since they run in the same circles, it could just be that they were being drunk and flirty.
But seeing as Leo was in a relationship with model Camila Morrone at the time, being flirty doesn’t sound too good either. Several people claimed to see Jenner and DiCaprio talking for hours and getting very cozy and touchy-feely.
This one is unconfirmed, but considering Leo’s history with pretty blondes, it’s easy to assume he and "Shutter Island" co-star Michelle Williams at least had a one-night stand. The critically acclaimed 2010 Martin Scorsese film "Shutter Island" saw DiCaprio and Williams playing husband and wife.
After the filming wrapped up, the two were seen partying together and quite close, but nothing steamy was ever photographed. Michelle Williams is married to theater director Thomas Kail and has two gorgeous kids.