Hot Or Not: 15 Famous Beauties Leonardo DiCaprio Has Dated

Starting out his career as a child star, Leonardo DiCaprio appeared in movies like Critters 3 and shows like Growing Pains, long before the average person knew who he was. Making a name for himself with roles in the films What’s Eating Gilbert Grape, The Basketball Diaries, and Romeo + Juliet, he was on his way to being a heartthrob. Then, he got a part in James Cameron’s Titanic, a movie that spent years as the highest grossing film in history. That movie made him the go-to crush of millions of teens around the world.

Growing into a good-looking man who also happens to be a highly paid and celebrated movie star, it's safe to say that it hasn’t been all that hard for him to find women who are interested in him. Known for dating some of the most beautiful women in the world, sometimes it has seemed like he has a new "internationally lusted" woman on his shoulder at every turn. If you haven’t kept up on his dating life, we can’t blame you. But suffice it to say that he seems to have a type—extremely gorgeous gals that the rest of the world would kill for. On top of that, he typically doesn’t seem to be involved with them for overly lengthy periods of time. After all, that may stop him from bedding another famous woman. Looking at the incredibly impressive list of women he has been matched with inspired us to put together this list of fifteen famous beauties Leonardo DiCaprio has dated.

In order for someone to be considered for inclusion on this list, they need to have been linked to the famous actor in public at one time or another. Leo doesn’t always speak about his personal life very freely so we need to make it clear that we can’t speak with one hundred percent certainty about the nature of their relationships. That said, the gorgeous ladies you will find here are among the list of women that the media has concluded he has dated based on witness accounts, photographic evidence, or something else.

We'll let you decide if they are hot or not.


15 Eva Herzigová

A Czech model who took the world by storm, Eva Herzigová is one of a small list of models who came to be known as something close to a household name. First coming to prominence because of taking part in a Wonderbra campaign, it seems odd as she clearly didn’t need the help. Going on to work for companies like Guess Jeans and appear in the Victoria's Secret catalog and the Sports Illustrated Swimsuit Issue, she has received two of the most coveted gigs in the modeling world. In fact, she was so well-known as the personification of beauty that she took part in the 2006 Winter Olympics Opening Ceremony where she was cast as a goddess. Widely thought to have been involved with Leo, we put her in our fifteenth slot as she was married at the time so it was an affair at best.

14 Ashley Roberts


You may not know her name but if you were around in the first decade of the 2000's, then you are bound to remember the girl group Ashley Roberts was a part of. A member of The Pussycat Dolls, a group that was known for its intense dance moves and music, she had a hand in several beloved music videos. Best remembered for songs like “Don’t Cha,” “Buttons,” “When I Grow Up,” and “Beep” to name a few, at one time Ashley’s work was a radio and television mainstay. Said to have dated Leo in 2009, they were seen together at the time and reports say he went directly to her the second he entered a bar she was having fun in.

13 Demi Moore

A person that at one time received the largest pay cheque any woman has ever received in the history of Hollywood, Demi Moore has an important legacy. Known for movies like St. Elmo's Fire, Ghost, A Few Good Men, Indecent Proposal, Disclosure, and G.I. Jane to name but a few, she has played pivotal roles in several classic films. Someone who was one-half of two megastar couples, one with Bruce Willis and the other with Ashton Kutcher, if rumors are to be believed, she was also involved with a third big name actor. Of course, we are talking about Leo who she's said to have dated both in 1997 while still married to Bruce and again in 2012 while single.

12 Mădălina Diana Ghenea


A Romanian actress and model who has taken part in fashion shows across the world, including Japan, France, Italy, Germany, Austria, and more, Mădălina Ghenea is highly sought after for her work. Also seen in movies like Dom Hemingway, Youth, and Zoolander 2, her work in that field has mostly flown under the radar but certainly seems to be on the upswing. Still, despite a slew of professional achievements that have allowed her to gain a measure of fame around the world, in North America she is largely known for dating Leo DiCaprio. Said to have been involved with him during the latter part of 2011, the couple was captured on film while she visited him on the set of one of his films in Australia.

11 Bridget Hall

Born in Arkansas, Bridget Hall started modeling at the remarkable age of ten before making the move to New York City and turning herself into one of the first women designated by some as a supermodel. Listed by Forbes Magazine as one of the “best ten” moneymaking models in the world at the age of seventeen, she was listed alongside women like Cindy Crawford and Christy Turlington. Having graced a long list of magazine covers over the years, including Elle, Vogue, Allure, and a lot more, millions of people had a thing for her at the height of her career. Choosing Leonardo instead of the rest, at an early stage of his career, Bridget is said to be the first major model to become involved with the actor.

10 Brittany Daniel


An actress who has never quite become a gigantic star, Brittany Daniel is a natural beauty. Introduced to many alongside her identical twin sister, Cynthia Daniel, as the main characters in the syndicated teen drama Sweet Valley High, the twins also appeared in The Basketball Diaries together. Having also acted in movies like Joe Dirt and its sequel, Dirty, White Chicks, Club Dread, Little Man, and Skyline, she has received roles in major movies for decades now. Having met Leonardo DiCaprio when he was the star of the aforementioned film, The Basketball Diaries, they must have hit it off as the pair dated for quite some time.

9 Kelly Rohrbach

Someone who went to Georgetown University on an athletic scholarship due to her golfing skills, Kelly Rohrbach clearly is a talented woman. Still, her looks are her greatest claim to fame as she is a successful model who has appeared in commercials for companies like Gap and Old Navy before appearing in Sports Illustrated’s Swimsuit Issue. Also someone with a fair amount of acting experience, she has appeared on shows like Two and A Half Men, The New Normal, and Rush on top of being set to play a part in 2017’s movie remake of Baywatch. Said to have been involved with the movie star from April to December of 2015, they weren’t together for a long time. A rare situation for Leo, if you ask me.


8 Natasha Henstridge


An actress that is principally known for her role as a pair of human and alien hybrids in the Species franchise of films, they are largely remembered for the beauty of their star and her several nude scenes. Of course, that isn’t the only work Natasha Henstridge managed to receive as she was also cast in Maximum Risk, The Whole Nine Yards, Ghosts of Mars, The Whole Ten Yards, and Deception. Someone that was blessed with one of the best bodies we’ve ever seen and the facial features of a model, we are surprised that she never received more fame for her work in that business. Said to have dated Leonardo some time between 1997 and 1998, it was taken so seriously that at one time people even believed that he may be the father of a child she gave birth to. She would go on to reveal the true father later on, though.

7 Naomi Campbell

A model with a career to die for, calling Naomi Campbell a supermodel almost doesn’t seem enough as evidenced by the fact that Interview Magazine once called her “the reigning megamodel of the all.” She may not be at the height of the industry like she was at one time, but she looks as good or better than ever. As a matter of fact, Naomi still gets constant work despite her first media job coming all the way back in 1978. Also a very outspoken woman who fought against racism in the business, she broke ground as the first black woman to grace the cover of magazines like the British version of Vogue. Evidently involved with Leonardo in 1995, years before his biggest roles came around, she clearly liked him for his looks.

6 Claire Danes


Having co-starred in the beloved Shakespeare adaptation Romeo + Juliet, if reports are true while working on the film, Leo and Claire Danes did not actually get along. Someone with a long-lasting career that has seen her take on memorable television roles in My So-Called Life and Homeland, it is incredible that they aren’t even her greatest claim to fame. Instead, it is her film work that has made up the majority of her career including performances in movies like U Turn, Brokedown Palace, Igby Goes Down, and Terminator 3: Rise of the Machines. Despite the fact that this duo has denied having a romantic relationship, rumors persist to this day that they were, in fact, a couple in the past.

5 Bar Refaeli

Another supermodel who has been near the top of the industry during her career, any fatigue you might have felt on reading about models should be quelled by getting to look at a photo of her. Given first place in Maxim Magazine’s Hot 100 list in 2012 and chosen to grace the cover of the 2009 Sports Illustrated Swimsuit Issue, when looking at Bar Refaeli, your brain almost wants to shut down with lust. Also a budding television star, she has appeared on shows like House of Style, was a guest judge on Germany’s Next Top Model, and used to host The X Factor Israel. In short, if there is a job out there that is made easier to get by being a world class beauty, then she is likely to get it. That includes dating a man like Leonardo. Having dated him at two separate times in her life, between 2006 and 2009 as well as 2010 and 2011, she clearly has an intoxicating presence for him.

4 Nina Agdal


A Danish model that seems to be born for the profession, Nina Agdal looks like someone who would be gorgeous straight out of bed despite having a number of makeup artists to alter her looks. Agdal has worked for companies like Billabong, Victoria’s Secret, Adore Me, and the Sports Illustrated Swimsuit Issue which she started with in 2012 and has been a mainstay ever since. Arguably the most anticipated publication in the world each year, it speaks volumes that she and two others graced the cover of the 50th Anniversary Issue of the aforementioned Swimsuit Issue. Said to have started seeing Leo in 2016, as far as we know, they may still be together today. At least Wikipedia says they are so that has to be true, right?

3 Helena Christensen

A former beauty queen who transitioned into a career having her photo taken, this Danish model is said to be one of the original seven women that became the biggest stars in the modeling world. Also remembered for starring in Chris Isaak’s “Wicked Game” music video, MTV named it the “sexiest video of all time” and we give Helena Christensen the lion’s share of the credit for that. We’d keep going but making any attempt to list all of the accolades she has won over her career, including Miss Universe Denmark, would go on for far too long. One of the most unique supermodels in history, Helena Christensen has the look of a person with supreme confidence and seems like someone who knows what she wants and knows exactly how to get it. It therefore makes perfect sense that it is said she was the first model to become involved with Leo after the biggest film of his career, Titanic, came out.

2 Gisele Bündchen


Much of the world knows that this Brazilian supermodel is currently married to Tom Brady, one of the best-known athletes alive but that wasn’t always the case. Having been previously named the 16th richest woman in entertainment, the top-earning model in the world, and even the 89th most powerful woman alive, it is clear that her mark has been felt. To put in perspective that Gisele Bündchen's looks are largely responsible for such accolades (her work ethic and drive are certainly involved too) is an evidence of just how hot she truly is. Also, a woman that has been involved in philanthropic efforts throughout her career, especially when it comes to the environment and her work as a Goodwill Ambassador, she has used her platform for positivity. She also met Leo due to being a celebrity too, which led to them dating between 2000 and 2005.

1 Blake Lively

An actress who became a known entity as one of the stars of Gossip Girl, a teen drama that ran for five years, Blake Lively is one of the most beautiful women in an industry filled with gorgeous-looking gals. Also known for movies like The Sisterhood of the Traveling Pants, Accepted, The Town, Green Lantern, and Savages, her film career has largely fallen short of expectations. That was until 2016’s The Shallows, a shark film that was a surprise hit and had many people praising her work. When looking at Blake, she brings to mind an era of beautiful blonde bombshells off yore and seems like the type of woman that inspires songs, sonnets, and every other piece of art. Having been spotted and photographed out and about with Leo, the pair seems to have had a whirlwind five-month relationship.

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