Claire Danes
We know that Claire Danes is now a loving and a high-profile husband, but way back when she was only a teenager, she is known to be the on-screen love of Leonardo DiCaprio. The issue about their whole on-set love story runs the entire gamut. According to other sources, when Claire Danes was only 16 years old, she found Lee, a 22-year-old actor, unprofessional. But, this claim was later on opposed by her recent confession that she had secret feelings for Leo while they were filing Romeo and Juliet.
Claire Danes
Naomi Campbell
DiCaprio may not have a hit movie back in the year 1995, but he made sure to know how to find the biggest hit girl’s names on the runway, knowing that he was only entering adulthood. Naomi and Leonardo enjoyed each other’s company for a brief period of time and had a sort of fling back in the day, even though they never seemed to have a serious relationship. At that time, experimenting with your love life is normal, but it seems that Leo has not left those days behind.
Naomi Campbell
Natasha Henstridge
Natasha Henstridge was not the first model DiCaprio was linked to, but because of her acting aspirations, it is with no wonder that their relationship wasn’t built for it to last. At the time when Natasha and Leonardo were introduced to each other, Leo was known to be at the edge of his acting career becoming an A-list star because of the release of Titanic. While on the other hand, Natasha had experienced her first success being an actress. These two never went out to the public with their romance.
Natasha Henstridge
Bijou Phillips
Leonardo DiCaprio seems to be a young man who is quite more experimental when it comes to his choice of taste with women. It is said that Phillips was not exactly the type of Leo. Leonardo DiCaprio usually prefers those leggy blonde models. Even so, their relationship was proved to be advantageous, no matter how short it was back then. Bijou Phillips came from a showbiz family, but it was Leonardo DiCaprio who made a way to connect her to the director that made her first film, Black and White.
Bijou Phillips
Trishelle Cannatella
After the film “The Real World” came to an end, the main actress Trishelle Cannatella had faded into obscurity. But, if the spreading rumors that time is said to be truthful and legitimate, Leonardo DiCaprio was the one who noticed her. During the time that Trishelle Cannatella came to her off period, Leonardo DiCaprio was known to be linked with one of the first reality stars to make waves to the public. Given Leonardo DiCaprio’s relationship status back then, we only have the words of Trishelle Cannatella to go off.
Trishelle Cannatella
Kidada Jones
Leonardo DiCaprio has been captured with several photos together with Kidada Jones back in the year 1990. The name of Kidada Jones is kind of a familiar sound because of her father Quincy Jones. These two never confirmed that they had a relationship back then because it is also possible that Kidada and Leo just enjoyed each other’s company. This was just before Leo began his relationship with Gisele Bundchen. And for Kidada, after being engaged with the rapper Tupac Shaku, having Leo was just a drop in the bucket.
Kidada Jones
Eva Herzigova
Leonardo is said to be a man that is not so much attached after a relationship. It wouldn’t be long before he moved on from his previous relationship to a new one. This new relationship is with another model who is named as Eva Herzigova. He was considered to be the biggest star in the world when he was introduced to Eva at a film premiere for “The Man in the Iron Mask”. He knew that he had to pursue a romantic relationship with her which ended up short again.
Eva Herzigova
Bar Refaeli
After things falling apart between Leonardo DiCaprio and Gisele Bundchen, it seemed that the only way for Leo to heal his broken heart was to find another internationally lauded and a blonde supermodel. After his previous relationship, he fell into the arms of a woman named Bar Rafaeli. They met each other at a Sports Illustrated party in Las Vegas. Compared to Leonardo and Gisele’s relationship, Leo and Bar would pursue each other on and off between the years of 2005 to 2011, they decided to break up for good.
Bar Refaeli
Anne Vyalitsyna
After having a rough patch that Leonardo had with Rafaeli, Leo found himself single again. He had gone after a model who both graced Sports Illustrated and was a Victoria’s Secret angel named Anne Vyalitsyna. The Russian-born model and Leo shared a brief fling during Leonardo’s six-month break. These two were spotted travelling together to glamorous locations. Without Anne knowing, here was still another woman who had a hold on Leonardo’s heart, which made it impossible for them to get more serious in their relationship. They had soon broken up.
Anne Vyalitsyna
Blake Lively
Blake Lively is way different among the other girls that Leonardo DiCaprio encountered. She was not a model intrinsically but having long legs and sunny locks are the things that made her to be a dead ringer for the kind of girl that Leo likes to pursue. As time passed by with their relationship, Leonardo discovered that Blake was not very like much like the other girls that he had been dating. Blake Lively would love to cook and bake for Leo which he never experienced in his past relationship.
Blake Lively
Gisele Bundchen
It is with high hopes that there was a significant amount of time where we believed that Leo had finally found the women he will love for the rest of his life. For five long years, Leo was in a relationship with the supermodel Gisele Bundchen. It is said that Leo was so serious of Gisele wherein he even brought Gisele along with him to the Oscars. The pair couldn’t just manage to take the next step. The two split up and Gisele, later on, found love with Tom Brandy.
Gisele Bundchen
Helena Christiansen
After Leonardo DiCaprio’s acting career soared high in the mid-1990s because of his hit movie “Romeo and Juliet” it was given that he searched for the biggest names at the Victoria’s Secret Fashion Show. And one of the best-known angels that time, even today, was Helena Christiansen. Back in 1997, she probably had a bigger name than Leonardo DiCaprio himself. With the rumors that these two were dating, the entire Hollywood waited to witness what would happen with this beautiful pair, but unfortunately, it was not to last.
Helena Christiansen
Madalina Ghenea
After the alleged break up that happened with Leonardo DiCaprio and Bar Rafaeli, a brunette woman made an appearance on Leonardo’s arms for a short period of time. The brunette woman is known to be Madalina Ghenea. These two were seen fondling each other at Leo’s temporary house in Sydney while filming his movie “The Great Gatsby”. Most people, especially the Americans, Romanians, and the Italians were obsessed about the arousing romance of the pair. Seeing Madalina Ghenea with Leonardo DiCaprio was an exciting piece of news for these people.
Madalina Ghenea
Alyce Crawford
Alyce Crawford, an Australian model who still says that she and Leonardo DiCaprio never really dated. But after seeing how frequently these two saw each other back when Leonardo was working on “The Great Gatsby”, it is hard to say if something was kept as a secret to the public. According to sources, it is claimed that Alyce has been going to Leo’s hotel but the two were only cautious about them being seen together in the public. Anything is possible, especially Leo was going through a rough romantic period.
Alyce Crawford
Erin Heatherton
After Leonardo DiCaprio’s brief interlude with an actress, he found a way to run back into the arms of models, Erin Heatherton, who was Victoria’s Secret model. Erin Heatherton and Leonardo DiCaprio enjoyed each other’s company. They managed to keep their relationship healthy for nearly a year between 2011 and 2012. Unfortunately, according to them, their schedules were too crazy and this resulted in both of them not keeping up with each other. They ended their relationship approximately 10 months after they were introduced to one another.
Erin Heatherton
Miranda Kerr
Leonardo never went public about his hidden fling with Miranda Kerr. This is because they were seen together in public while Miranda was still married to Orlando Bloom, who was an actor that time. In 2013, Kerr and Bloom announced their break up. But in spite of this announcement, it is said that Leo and Kerr were going out since 2012. Does this act contributed to Kerr and Bloom’s break up or Kerr really did it because she knew that a divorce was coming their way? We may never know.
Miranda Kerr
Margarita Gauchet
Margarita Gauchet is a French model who gave Leo a break from all his women who were blonde. In 2012, they were seen getting cozy on a yacht wherein, this kind of trip is one of the favorite ways of Leonardo on how he romances his women. However, their relationship didn’t take as long as others expected. Their romance was something more than just a public hug and a public kiss. With that being said, these two denied that their tryst took place, though they both did not work out.
Margarita Gauchet
Kat Torres
By the year 2013, Leonardo DiCaprio decided to take his sights on another Brazilian model, Kat Torres. Torres and DiCaprio ran into each other’s attention at the Cannes that year. Seeing through the looks of Kat Torres, she fits perfectly with Leo’s type, but it seemed that there wasn’t much chemistry between the two of them, as their relationship was short-lived. That time, DiCaprio’ heart was still into another woman even though he was with Torres. It may be because of Torres’ quick blab when it comes to their relationship.
Kat Torres
Alesia Riabenkova
Much as the actress Alesia Riabenkova’s time spent in the spotlight, this has nothing to do with Leonardo DiCaprio. There was arousing news at that time that there were some wild claims that she was being attacked by a photographer in which this scenario could not be proven as true. That time, she was experiencing a heart break after her public break up with a Scottish actor. There were also rumors that sprung up that after the split that Alesia Riabenkova encountered, she was healing her heart with Leonardo DiCaprio.
Alesia Riabenkova
Toni Garrn
After Leonardo DiCaprio’s not so sure relationship with Kat Torres, this time Leonardo DiCaprio pursued a woman from Germany who is also a blonde model, Toni Garrn. Leo and Toni were dating on and off between the years of 2013 and 2014. It seems that Leonardo DiCaprio was fearless to go back and rekindle that relationship that they had back then. Years after their break up, these two were seen strolling down the street while holding each other’s hands, but later on, their bliss would be cut short once again.
Toni Garrn
Katie Cleary
Katie Cleary was an established actress in franchise movies like the “Iron Man 2”, she didn’t necessarily need a man like Leonardo DiCaprio to further her career in acting. But Katie Cleary needed a man like Leo when it comes to blowing up her soon failing marriage. Katie had filed a divorce against her husband that time. Many believed that this photo of Katie Cleary right here, was an image taken from a party with Leonardo DiCaprio and was believed to be the nail in the coffin for her husband.
Katie Cleary
Demi Moore
Back in time when Leonardo DiCaprio had a chance to go out with a lady like Demi Moore, it seemed like Leo was still exploring how it feels to be in a relationship with an older woman than him. It is obvious just from looking that Demi Moore looks older than the younger girlfriend that Leonardo DiCaprio had. Demi Moore was on the hunt for a younger man after her split with Bruce Willis. It was clear to her that Leonardo was not the man who was meant for her.
Demi Moore
Rihanna
Looking back in 2015, it seemed like Leonardo DiCaprio and Rihanna were often found to be in the same party. Though these two were not seen going out in the public and didn’t confirm that there was something going on between the two of them, Leo was often seen to be photographed a step behind Rihanna with his hat pulled lower so that his face would not be seen. But then the press discovered the fact that Rihanna had been linked to one of Leo’s friends and not Leo himself.
Rihanna
Kelly Rohrbach
When these two, Kelly Rohrback and Leonardo DiCaprio, started their romance, it seems like they have the chemistry to become a couple that everyone can admire and a relationship that will last for a long period of time. They were seen laying it on thick through the streets of New York City and it came with no surprise for the people to know about the announcement of their inevitable break up. For Leonardo DiCaprio, his relationship with Kelly Rohrbach is just like the others, he treated them all with love.
Kelly Rohrbach
Laura Whitmore
Some people were highly surprised when it appeared that Leonardo DiCaprio was cozying up to an Irish television presenter, Laura Whitmore. These two were said to meet at an awards show and that Leo showed his admiration to Laura at the after-party. Every time Laura Whitmore is asked whether or not she had any kind of relationship with Leonardo DiCaprio, she would usually play coy and give a non- direct answer about the issue. She only would say to the reporters that everyone was just having fun that night.
Laura Whitmore
Nina Agdal
Leonardo DiCaprio is the type of person that wants everything to be as private as possible especially when it comes to his personal life. But he cannot hide from any paparazzi that are spread from any place he could go. He was spotted together with the 21-year-old and a Sports Illustrated model, Nina Agdal. She then claimed that the much older actor never made a move on her and that they were only friends, but considering how Leo acts around girls he had gone outside, this might not be true.
Nina Agdal
Roxy Horner
As the sources say, Leonardo DiCaprio met Roxy Horner as his last relationship was falling apart, which was never considered to be a good time, to begin with a new romance again. Even though Roxy became part of Leo’s restless period of his love life, Roxy still denied the said rumors about both of them. However, the two were spotted again, which for people doesn’t look like just friends but more of a partner. The two continued to be friends and any reports made were considered to be false.
Roxy Horner
Chelsey Weimar
Way back in 2016, Leonardo DiCaprio seemed to have a difficult time finding an appropriate partner with whom he could spend his entire life full of love and affection. One of his romances at that time was the 19 or 20-year-old woman, Chelsey Weimar. Though both of them never went to the public when it comes to their relationship, they were seen having dinner together in a restaurant. While some of Chelsey Weimar’s posts on Instagram were taken from Leonardo DiCaprio’s house in Los Angeles, their love story didn’t last.
Chelsey Weimar
Ella Ross
It said that 2016 was simply the year of the British models for Leo. After Leo was said to be linked to Scott Disick, a woman named Ella seemed to be looking for an upgrade, finding someone who would earn their celebrity. None of Ella and Leonardo DiCaprio waited for any time to settle what happened to their personal previous relationships and why it had come to an end. They were then spotted dancing not with each other but close to one another at a party filled with famous people.
Ella Ross
Victoria Robinson
Victoria Robinson, a 23-year-old and one of the few brunettes that Leo had spent time with since his huge Hollywood break a few decades ago. Just like the other relationship that DiCaprio had, the relationship he had with this 23-year-old brunette is nothing more than a fling and cannot upgrade it to the next level. The rumors began when the two were spotted leaving a Justin Biebers’ party last spring of 2016. Again, as Leonardo was trying to find the one to spend his whole lifetime, their relationship didn’t last.
Victoria Robinson
Lorena Rae
When Lorena Rae showed in the picture of Leo’s love story, there was something within her that made her distinctly different. The 23-year-old German still qualifies to Leo’s qualification of being a model, but she is one of the few brunettes Leo has stepped out within the recent years. Their love story started sometime around in August 2017. Leonardo DiCaprio enjoys the company that Lorena Rae is giving him but as he was trying to woo Lorena, he was also hitting up with his ex, Toni Gurrn in the town.
Lorena Rae
Ela Kawalec
When things didn’t go well with the former ladies of Leonardo DiCaprio, he then set his focus on the Polish model named Ela Kawalec. It is observed that in the recent year, Leonardo DiCaprio’s strategy of winning new girlfriends is by taking them out for a spin around the streets of New York City, often by taking advantage of the thing called Citi Bike, which is the city’s bike share program. Just like other Leonardo DiCaprio’s girlfriends’ careers go, Ela Kalawec still managed to do numerous photoshoots of the beachsides.
Ela Kawalec
Kristen Zang
If there is one ex to end all the exes that Leo had, then it is probably Kristen Zang. Leo was really in love with Kristen that he even took her to the premiere of Romeo+Juliet way back in the 1997’s. Leo was enamored by this blonde model. Sadly for Leonardo, by the time he reached the top because of his movie Titanic, Leo and Kristen had already broken up. For some, they say that Kristen was the “one that got away” of Leonardo, but then, we may never know.
Kristen Zang
Bridget Hall
Leonardo DiCaprio achieved his heartthrob status when he was nearly 20 years of age, but two decades later or more, he’s still embarking on romance to the most beautiful models that he has ever known in his entire life. Leo’s passion and love for selective models started when he was still young, as he finds himself happy to show off Bridget Hall as his first public girlfriend all the way back in the year 1994. But sadly for the fans, especially for them, their puppy love was not to last.
Bridget Hall
Juliette Perkins
It may be clear for Leonardo DiCaprio that rekindling a fling or bringing back a love that was once lost like what he did with Lorena Rae, was the right move for him to do. But as he searched for the women whom he could call his one and only, he was then introduced to a stunning 19-year-old, Juliette Perkins. Juliette Perkins is known to be one of the youngest girls that Leonardo DiCaprio ever dated. But despite their age gap, this didn’t stop them from leaving several parties together.
Juliette Perkins
Brittany Daniel
As Leonardo DiCaprio started filming “The Basketball Diaries” way back 1995, he had new female co-stars beside him, wherein he could be romantically linked to. As Leo’s career in acting continues to rise, it is with no surprise that the young heartthrob was all over the news because of his love life. None of Leonardo DiCaprio and Brittany Daniel admitted that they had some kind of relationship, but considering the chemistry that they have on-screen, there is definitely a big possibility that the two had a fling off the camera.
Brittany Daniel
Paris Hilton
Dating a socially prominent person is not one of Leonardo DiCaprio’s taste. But in the year 2000, these two, Paris Hilton and Leonardo DiCaprio, end up running in the same social lines and circles. Being friends is not necessarily a prerequisite for a romantic relationship. These two were often seen being in the same place at the same time which immediately began whispers from other people that these two are possibly linked to one another. But of course, noticing the behavior of Leo, it wasn’t long enough before Leo had moved on.
Paris Hilton
Camila Morrone
In the past couple of weeks that have passed, Leonardo DiCaprio seems like he may have found his long-awaited romantic bliss, as he announced publicly that he was dating a young model, a 21-year-old, Camila Morrone. Besides the pretty young model Camila Morone, who was born in the year the Titanic debuted, he has no other girl than her that lasted longer than six months since he dated Erin Heatherton way back the year 2012. Is Camila Morrone going to be the one Leo waited for his entire life?
Camila Morrone
Kate Winslet
Kate Winslet and Leonardo DiCaprio may have continued to decline that they never had a romantic relationship, it is crystal clear from their long-lasting friendship that they have been by each other’s side for the past two decades. While knowing Leo was flirting from model to model, on the other hand, Kate managed to have three separate marriages. Their commitment to one another as being friends has never wavered. Perhaps, there is a reason behind what is happening in their lives? Maybe they have always been waiting for each other.
Kate Winslet