Women Leonardo DiCaprio Has Dated Over the Past Two Decades |

Ever since Titanic, his critically acclaimed film, was released, Leonardo DiCaprio has captured the public’s interest. He suddenly discovered that a large group of young women had made him their favorite young heartthrob. Leo quickly got used to dating models, and several of them went to some of his biggest premieres with him. Even though some of these women might have been the love of his life, for his biggest success, he only had his co-star Kate Winslet on his arm. It wouldn’t take long for Leo to advance through the supermodel ranks, attracting ever-more accomplished women. But which woman has his heart in truth?

Bridget Hall

Leonardo DiCaprio may have become a heartthrob when he was just 20 years old, but more than 20 years later, he’s still starting relationships with some of the world’s most attractive models.

Leo developed a passion for models early on, proudly introducing Bridget Hall as his first known girlfriend in 1994. Sadly, their infatuation did not last. Which movie star is his true love, then?

Brittany Daniel

Leo had a new female costar with whom he could develop romantic ties when he started filming The Basketball Diaries in 1995. It’s not surprising that Leo, a young heartthrob, was in the news for his romantic relationships as his profile as an actor continued to rise.

There is a chance that Leo and Brittany had a fling while they were working on the movie, although neither Leo nor Brittany ever officially confirmed their relationship. This is because of their on-screen chemistry.

Claire Danes

Although Claire Danes now has a famous husband of her own, Leonardo DiCaprio used to make her his on-screen love when she was a young woman. Their on-set relationship has been the subject of numerous rumors.

According to some sources, even though Claire was only 16 years old, she thought Leo, 22, was unprofessional. Her recent admission that she had a crush on him while they were filming Romeo + Juliet stands in stark contrast to that. Danes implies that nothing occurred, but it’s difficult to be certain.

Helena Christiansen

Leo looked for the biggest names at the Victoria’s Secret Fashion Show as his career took off in the middle of the 1990s thanks to hits like Romeo+Juliet.

Even though Helena Christiansen is one of the most well-known Angels today, in 1997 she may have even been more well-known than Leonardo DiCaprio. It was pretty obvious something was going on based on the number of parties they attended together, even though he may not have ever made it public.

Naomi Campbell

Leo may not have reached his peak as a movie star in 1995, but even as a young adult, he was able to identify the biggest names on the runway.

Even though it never seemed like he and Naomi Campbell had a serious relationship, there was a rumor back then that the two had at least a brief fling. It’s common to experiment with your romantic life at that age, though it seems Leo hasn’t quite moved past those times.

Kristen Zang

Kristen Zang may very well be Leo’s one and only ex when it comes to relationships. Leo was so taken with this particular blonde model back in 1997 that he even brought her to the Romeo+Juliet premiere.

Sadly for the rising star, they had already split up by the time Titanic actually reached the top of the charts. Some claim that Zang is “the one that got away,” but Leo’s life could hold greater love.

Demi Moore

It appears that Leonardo DiCaprio was experimenting with what a relationship with an older woman might be like when he went on a few outings with Demi Moore.

Young Leo doesn’t appear to be as enthralled with Demi as his much younger girlfriends do these days, and instead he appears to be struggling a little. Even if she had been looking for a younger man after her breakup with Bruce Willis, Leonardo DiCaprio was obviously not that man.

Natasha Henstridge

Although Natasha Henstridge wasn’t the first model Leo was linked to, it’s understandable why the relationship didn’t work out given her desire to pursue acting.

Leo was on the verge of becoming an A-list celebrity after the release of Titanic at the time Natasha and Leo were first introduced to one another, and Natasha had already tasted success as an actor rather than a model. They never really made their relationship public.

Bijou Phillips

Leo’s choice of women seems to have been a little more daring when he was a younger man. In the 1990s, Bijou Phillips wasn’t exactly the type of lanky blonde model Leo would later prefer.

Nevertheless, it appears that their relationship—however brief—served them well. Phillips may have been born into a show business family, but Leonardo DiCaprio was the one who put her in touch with the producer of her debut movie, Black and White.

Eva Herzigova

After a short period of time, Leo moved on from his previous relationship and began a new one with Eva Herzigova, another model.

Even though he was the most famous person on the planet, he knew he had to pursue a romantic relationship with the Czech beauty after meeting her at the 1998 premiere of The Man in the Iron Mask. Their relationship would end up being brief, just like many of his other flings since becoming well-known.

Kidada Jones

Leo and Kidada Jones appeared in several photographs taken in the late 1990s. Her father is Quincy Jones, so if the name seems a little recognizable, that’s because it is.

Leo and Kidada never confirmed their relationship, but it’s possible that they had a brief relationship before Leo started dating Gisele Bundchen. After being engaged to the rapper Tupac Shakur, dating Leo was a drop in the ocean for Kidada.

Trishelle Cannatella

Trishelle Cannatella may have vanished from view soon after her stint on The Real World ended, but if the rumors are accurate, Leo DiCaprio at least took notice of her.

Leo was associated with one of the first reality stars to become well-known to the general public during what must have been a rough time with Gisele. Of course, we only have Trishelle’s word to go on given Leo’s relationship status at the time.

Paris Hilton

Leo DiCaprio may not typically date socialites, but in 2000, Paris Hilton and Leo DiCaprio ended up hanging out in the same social circles.

Although having mutual friends is not a requirement for a romantic relationship, rumors of a relationship between Paris and Leo started to circulate when the two of them started frequently showing up at the same location at the same time. Leo had obviously moved on to better and bigger things very quickly.

Gisele Bundchen

It might be difficult to imagine that there was a period of time when we thought Leo had finally found the one. Leo’s go-to companion for five years straight after he was associated with Paris Hilton was supermodel Gisele Bundchen.

Leo took his relationship with Gisele very seriously and even brought her to the Oscars. But for some reason, they were unable to proceed to the next step. Gisele fell in love with Tom Brady after they got divorced.

Bar Refaeli

Leo seemed to think that the only way to heal his wounds after his relationship with Gisele ended was to find yet another highly acclaimed blonde supermodel.

This time, he met Bar Refaeli at a Sports Illustrated party in Las Vegas and immediately fell into her arms. Leo and Bar pursued each other intermittently between 2005 and 2011 when they finally called it quits. However, they may not have been as serious about their relationship as he and Gisele were.

Anne Vyalitsyna

During a difficult time with Bar, Leo found himself free enough to pursue Russian-born Anne Vyalitsyna, a model who had appeared in Sports Illustrated and was a Victoria’s Secret angel.

During Leo’s six-month break, the two had a brief relationship during which they frequently appeared in public in posh places like Ibiza. Little did Anne know that Leo’s heart still belonged to another woman, preventing them from developing a more serious relationship. They would soon split up.

Blake Lively

Although Blake Lively isn’t a model in the traditional sense, she is eerily similar to the type of woman Leo likes to chase with her long legs and bright locks.

Leo would soon come to realize that Blake was unlike the other women he had been dating as soon as things between them heated up. Blake seemed to enjoy baking and cooking for Leo, which was something he had never experienced in any of his prior relationships.

Madalina Ghenea

The brunette Madalina Ghenea briefly showed up on Leo’s arm during the difficult time following their breakup with Bar Rafaeli. While he was in Sydney filming The Great Gatsby, the couple was spotted making out at his temporary residence.

Not only Americans were enamored with the developing romance. The news that she would be starring alongside Leonardo DiCaprio was especially exciting because both Italians and Romanians can’t get enough of their respective stars.

Alyce Crawford

Alyce Crawford, an Australian model, continues to insist that she and Leo never really dated, but given how frequently they crossed paths in 2011 when Leo was filming The Great Gatsby, it’s difficult to know if more is going on behind closed doors.

Although they were always wary of being seen together in public, several sources claimed to have seen Crawford go to Leo’s hotel. Anything is possible considering that Leo was going through a difficult romantic phase.

Erin Heatherton

Leo was happy to jump right back into the arms of models after his brief encounter with an actress, this time picking Erin Heatherton.

Leo enjoyed spending time with Erin, another Victoria’s Secret model, and they were able to make things work for almost a year between 2011 and 2012. Unfortunately, they terminated their relationship approximately 10 months after they first met one another, claiming that their hectic schedules prevented them from maintaining it.

Miranda Kerr

Leo never made a big deal out of his relationship with Miranda Kerr, which may have been due to the fact that they were frequently mentioned in the media while Kerr was still wed to actor Orlando Bloom.

Despite the fact that Kerr and Bloom only split up in 2013, there are rumors that she was seen with Leo in 2012. We may never know if this played a role in Kerr’s breakup with Bloom or if she was more likely to stray because she was aware that a divorce was imminent.

Margarita Gauchet

Leo received a break from his blondes when the French model was spotted cuddling up to him on a yacht in 2012. However, this relationship seems to have been even shorter than usual. The yacht trip seems to be one of Leo’s favorite ways to woo women.

Little information about their relationship has been revealed other than their public kiss. Even though it was obvious that their relationship didn’t work out, neither party has denied that they had a tryst.

Kat Torres

After running into each other at Cannes in 2013, Leo had his sights set on another Brazilian model. Torres matched Leo’s preferred aesthetic perfectly, but their relationship was remarkably brief, suggesting that there may not have been much chemistry between them.

DiCaprio’s constant switching between Torres and another woman who had a much stronger hold on his heart at the time most likely didn’t help. It might be a result of Torres’ hasty disclosure of the connection.

Alesia Riabenkova

Alesia Riabenkova spent a lot of time in the public eye for reasons unrelated to Leonardo DiCaprio. She gained notoriety after some outrageous claims that she had been attacked by a photographer were disproven.

She was dealing with the fallout from a highly publicized breakup with a Scottish actor at the time. Even the most necessary splits can be traumatic. After their breakup, there were rumors that model Alesia, who was born in Latvia, was reconciling with Leonardo DiCaprio.

Toni Garrn

Between Kat Torres and another blonde model, this one from Germany, Leo pursued her. Even though they had a sporadic relationship between 2013 and 2014, it appears that Leo wasn’t hesitant to restart their romance in 2017 when things fell apart with his most recent girlfriend.

The two were once again seen walking hand in hand down the street after a period of time apart, but their happiness would be again short-lived. These days, Leo prefers to stay as far away from Garrn as possible.

Katie Cleary

As a seasoned performer in blockbuster movies like Iron Man 2, Clearly didn’t necessarily need Leo to advance her career, but he was a viable option for ending a failing marriage.

Many people think that being photographed with the celebrity at a party was the final straw for her husband, even though it appears that Katie had long since checked out of her marriage as she had already filed for divorce.

Rihanna

Leo and Rihanna’s relationship has remained the subject of rumors, but for a while in 2015, it appeared as though they frequently attended the same events.

Leo was frequently pictured standing steps behind the pop star with a hat pulled low over his head, even though neither ever publicly acknowledged having a fling. After the fact, the media would learn that Rihanna had in fact been connected to Leo’s friend and not the other way around.

Kelly Rohrbach

When Kelly Rohrbach and Leonardo DiCaprio first started dating, there appeared to be enough spark between them to sustain their relationship.

No matter how frequently they were spotted laying it on thick in New York City, it was expected when they announced their impending split. Just because Leo appeared serious about his most recent model doesn’t mean it was any different from the others.

Laura Whitmore

Leo’s apparent closeness to Irish television host Laura Whitmore may have taken a few people by surprise. Leo was reportedly hot on her trail at the after-party after the two allegedly met at an awards show.

Whitmore avoided answering questions about whether or not she was dating Leo, only telling reporters that “everyone was just having fun—there was a lot of dancing.” In either case, it seems to have only been temporary.

Nina Agdal

Leo may prefer to keep his personal life as private as possible, but he hasn’t had much success keeping his relationships or trysts from the paparazzi.

When he was seen with 21-year-old Sports Illustrated model Nina Agdal, Nina tried to quickly clear the air by claiming that they were just friends. She insisted that the much older actor never made a move on her, but given how he responds to girls who come out in the open, that claim might not be entirely accurate.

Roxy Horner

As his previous relationship was breaking down, Leo met Roxy, which is never a good time to start a new romance. Horner denied rumors about their first encounter, despite the fact that she became a part of this unsettling time in his romantic life.

But a few months later, they were spotted once more, this time appearing less like friends and more like lovers. Horner insisted that they were just friends and that any claims to the contrary were untrue, despite what the rumors claimed.

Chelsey Weimar

Back in 2016, Leo seemed to have a rough time finding a partner with whom he could have anything more than a fling. One of his brief romances at the time was Chelsey Weimar, who then was around 19 or 20 years old.

Leo appeared to be having a hard time in 2016 finding someone with whom he could have anything more than a fling. Chelsey Weimar, who was around 19 or 20 years old at the time, was one of his brief flings.

Ella Ross

It’s possible that Leo’s 2016 was just the year of the British models. Ella Ross appeared to be seeking an upgrade after being associated with Scott Disick, at least in terms of dating a celebrity who had earned their notoriety.

When they were seen dancing close to one another at a celebrity-studded party, Leo and Ella hadn’t waited for the dust to settle after their previous relationships had ended.

Victoria Robinson

One of the few other brunettes Leo has dated since his big Hollywood break so many decades ago was the 23-year-old Victoria Robinson. His time with Robinson was nothing more than a fling, much like many of his other relationships at the time.

When Robinson and DiCaprio were spotted leaving one of Justin Bieber’s parties in the spring of 2016, rumors that they were dating started to circulate, but the romance reportedly fizzled out quickly.

Lorena Rae

When German model Lorena Rae, 23, entered the picture, there was immediately a difference between her and Leo’s other women. She’s one of the few brunettes he’s been spotted out with in recent years, but she’s still a model, as evidenced by her petite frame.

They appeared to start dating around August 2017, but even as he courted her, Toni Gurrn, his ex, was also enjoying himself out on the town. Without a doubt, it was short-lived.

Ela Kawalec

After his relationships with his two previous girlfriends both ended badly, Leo set his sights on the Polish model Ela Kawalec.

Leo seems to have adopted the strategy of taking prospective girlfriends on a tour of New York City in recent years, frequently by using Citi Bike, the city’s bike-sharing service. Ela was still a budding model in terms of Leo’s girlfriends’ careers, despite the numerous beachside photo shoots she’d managed to land.

Juliette Perkins

Leo might have realized that having a tryst with Lorena Rae or restarting a relationship with an ex weren’t the best choices for him. He was introduced to Juliette Perkins while looking for the one and only woman he could call his own, which undoubtedly raised a lot of eyebrows.

Although Juliette, who was 19 years old, is one of the youngest women Leo has dated since his own adolescence, their age difference didn’t prevent them from leaving several parties together.

Camila Morrone

Leo recently revealed that he was dating the young model Camila Morrone, giving the impression that he may have finally found the love of his life.

He had not been in a relationship that lasted longer than six months since he dated Erin Heatherton back in 2012 until he met the 21-year-old, who was born the year Titanic made its theatrical debut. Could Camila be the woman Leo is supposed to be with? Or is there another person who has been standing by all along?

Kate Winslet

Although Leonardo DiCaprio and Kate Winslet have insisted that they have never been romantically involved, it is obvious from their close friendship that they have been each other’s most dependable friends for the past 20 years.

Kate has survived three different marriages while Leo has been hopping from model to model, but their dedication to one another has never wavered. They may have simply been waiting for each other their entire relationship, which may be why their love lives have never been stable.