Now, this man is an idol. He is a god… and not just because of his looks or his acting prowess. It’s because of the women in his life.
Back in the early ’90s, we knew that this teen heartthrob would have several beautiful women beside him but boy, oh boy… Who would’ve thought that the numbers would be as many as this? And the beauty and hotness each possesses? Oh, Leonardo DiCaprio deserves a kneel from us. Yup, a hat tip just won’t be enough.
Claire Danes
Claire Danes may now have her own high-profile husband, but when she was a teenager, she was Leonardo DiCaprio’s on-screen love. The rumors about their on-set relationship are diverse. According to some sources, even though Claire was only 16, she thought 22-year-old Leo was unprofessional. That contradicts her recent admission that she had a crush on him while they were filming Romeo + Juliet. Claire Danes implies that nothing happened, but it’s difficult to know for sure.
Naomi Campbell
Leo may not have reached peak movie stardom in 1995, but even as a teenager, he knew how to find the biggest names on the runway. Though he and Naomi Campbell never seemed to have a serious relationship, there was a rumor back in the day that the two had a fling, at least for a short time. It’s normal to experiment with your love life at that age, but it appears Leo hasn’t quite left those days behind.
Natasha Henstridge
Natasha Henstridge was not the first model Leo was linked to, but given her acting ambitions, it’s no surprise the relationship didn’t last. Leo was on the verge of becoming an A-list star following the release of Titanic at the time Natasha and Leo were introduced, and Natasha had experienced her first taste of success as an actor rather than a model. The couple never made their relationship public.
Bijou Phillips
Leo appears to have been a little more daring in his choice of women when he was younger. In the 1990s, Bijou Phillips was not the type of leggy blonde model that Leo would prefer in his later years. However, it appears that their relationship, no matter how brief, was beneficial. Phillips was born into a showbiz family, but it was Leonardo DiCaprio who introduced her to the director who cast her in her first film, Black and White.
Kidada Jones
Leo was photographed with Kidada Jones in several photos taken in the late 1990s. If her name sounds familiar, it’s because her father’s name is Quincy Jones. While the two never confirmed a romance, it’s possible that Leo and Kidada had a brief romance before Leo started dating Gisele Bundchen. After being engaged to rapper Tupac Shakur, dating Leo was a drop in the bucket for Kidada.
Eva Herzigova
It wouldn’t be long before Leo moved on to a new relationship with another model, Eva Herzigova. When Leo met the Czech beauty at the premiere of The Man in the Iron Mask in 1998, he knew he had to pursue a romantic relationship with her. Their entanglement, like many of his other flings since his rise to fame would be fleeting.
Gisele Bundchen
It may be difficult to believe that there was a time when we thought Leo had finally found the one. For five years, Leo’s constant companion was supermodel Gisele Bundchen. Leo was so taken with Gisele that he brought her to the Oscars with him. However, for whatever reason, the pair was unable to take the next step. Gisele found love with Tom Brady after they divorced.
Trishelle Cannatella
Trishelle Cannatella may have faded into obscurity after her stint on The Real World ended, but if the rumors are true, at least Leo DiCaprio took notice of her. During what must have been a rough patch with Gisele Bundchen, Leo was linked to one of the first reality stars to make headlines. Of course, given Leo’s relationship status at the time, we can only rely on Trishelle’s word.
Bar Refaeli
When things fell apart with Gisele, it appeared that the only way Leo could lick his wounds was to find another internationally acclaimed, blonde supermodel. He fell into the arms of Bar Refaeli this time after meeting her at a Sports Illustrated party in Las Vegas. Though they were never as serious as he and Gisele, Leo, and Bar pursued each other on and off between 2005 and 2011, when they finally split up for good.
Anne Vyalitsyna
During a difficult period with Bar, Leo found himself single enough to pursue a model who had appeared in Sports Illustrated as well as Victoria’s Secret, Russian-born Anne Vyalitsyna. During Leo’s six-month break, the two were frequently spotted traipsing around glamorous locations like Ibiza. Anne had no idea that another woman still had a stranglehold on Leo’s heart, making it impossible for them to get serious. They’d soon split up.
Blake Lively
Blake Lively isn’t a model per se, but with her long legs and sunny locks, she’s a dead ringer for the type of girl Leo is looking for. When things started to heat up between Leo and Blake, he realized she was nothing like the other girls he had been dating. Blake was apparently happy to cook and bake for Leo, which he had never done in any of his previous relationships.
Helena Christensen
With hits like Romeo+Juliet launching Leo’s career in the mid-1990s, it was only natural that he sought out the biggest names at the Victoria’s Secret Fashion Show. Helena Christensen is still one of the most well-known Angels today, but back in 1997, she was possibly bigger than Leonardo DiCaprio himself. With the news that these two were dating, Hollywood was waiting to see what would happen between the stunning couple. Unfortunately, it would not last.
Madalina Ghenea
During Leo’s turbulent period following his split from Bar Rafaeli, the brunette Madalina Ghenea briefly appeared on his arm. While he was in Sydney filming The Great Gatsby, the two were seen canoodling at his temporary residence. Not only were Americans obsessed with the burgeoning romance. Both Romanians and Italians are obsessed with their own stars, so seeing her with DiCaprio was especially exciting.
Alyce Crawford
Alyce Crawford, an Australian model, maintains that she and Leo never dated, but given how frequently they saw each other back in 2011 while Leo was working on The Great Gatsby, it’s difficult to say if something more is being kept from the public. Several sources claimed to have seen Crawford leaving Leo’s hotel, but they were always wary of being seen together in public. Given that Leo was having a difficult romantic period, anything is possible.
Erin Heatherton
Following his brief affair with an actress, Leo was eager to return to the arms of models, this time Erin Heatherton. Erin was yet another Victoria’s Secret model with whom Leo enjoyed spending time, and they were able to keep things going for nearly a year between 2011 and 2012. Unfortunately, they claimed that their schedules were too hectic to keep their relationship going, and they ended their relationship roughly 10 months after they met.
Miranda Kerr
Leo never went public about his fling with Miranda Kerr, which may have been because they were linked together in several publications while Kerr was still married to the actor Orlando Bloom. Though Kerr and Bloom announced their split in 2013, she was reportedly seen out and about with Leo in 2012. We’ll never know if this contributed to her breakup with Bloom or if Kerr was prone to straying because she knew a divorce was on the way.
Margarita Gauchet
The French model gave Leo a break from his blondes when they were seen getting cozy on a yacht in 2012. The yacht trip appears to be one of Leo’s favorite ways to romance women, but his relationship with Margarita Gauchet appears to have lasted even less than usual. Aside from their public kiss, little is known about this romance. Having said that, neither has denied that their affair occurred, even though it clearly did not work out between the two.
Kat Torres
After meeting another Brazilian model at Cannes that year, Leo had set his sights on another Brazilian model by 2013. Though Kat Torres matched Leo’s preferred aesthetic, there didn’t appear to be much chemistry between the two of them, as their relationship was extremely brief. It didn’t help that DiCaprio was torn between Torres and another woman who had a much stronger hold on his heart at the time. It could be because Torres was so quick to reveal the relationship.
Alesia Riabenkova
Alesia Riabenkova‘s time in the spotlight had little to do with Leonardo DiCaprio. She made headlines after some outrageous claims about being attacked by a photographer were proven false. She was dealing with the fallout from a public breakup with a Scottish actor at the time. Even the most necessary of splits can be painful. Following the split, there were rumors that Alesia, a Latvian-born model, was healing her heart with Leonardo DiCaprio.
Toni Garrn
Leo pursued another blonde model, this time from Germany, to complement his relationship with Kat Torres. Though the pair dated on and off between 2013 and 2014, it appears that Leo wasn’t afraid to rekindle their romance when things fell apart with his current flame in 2017. After several years apart, the two were seen strolling down the street hand in hand, but their happiness was cut short once more. Leo now prefers to avoid running into Toni Garrn whenever possible.
Katie Cleary
Katie Clearly didn’t need Leo to advance her career as an established actress in franchise films like Iron Man 2, but he was a good option when it came to blowing up a failing marriage. While it appears that Katie had already filed for divorce, many believe that being photographed with the star at a party was the final nail in the coffin for her husband.
Demi Moore
When Leonardo DiCaprio went out with Demi Moore, it appears he was experimenting with what a relationship with an older woman might be like. Far from being enthralled as his much younger girlfriends appear to be with him these days, young Leo appears to be suffering from the more worldly Demi. Even if she was looking for a younger man after her divorce from Bruce Willis, Leonardo DiCaprio was clearly not that man.
Rihanna
This relationship has remained a rumor, but for a period of time in 2015, it appeared that Leo and Rihanna were frequently seen at the same party. Though neither went public with their relationship, Leo was frequently photographed steps behind the pop star with a hat pulled low over his head. Rihanna had been linked to one of Leo’s friends, not Leo, as the press discovered after the fact.
Kelly Rohrbach
When Leonardo DiCaprio and Kelly Rohrbach first started dating, it appeared that there was enough spark between them to make this fling last. It came as no surprise when they announced their inevitable breakup, despite how frequently they were seen laying it on thick throughout New York City. Just because Leo seemed serious about his latest model didn’t mean it was necessarily any different from the others.
Laura Whitmore
Some may have been taken aback when it appeared that Leo was getting cozy with Laura Whitmore, an Irish television presenter. The two apparently met at an awards ceremony, and Leo was hot on her tail at the after-party. Though Whitmore was coy when asked if she had a relationship with Leo, she only told reporters, “Everyone was just having fun—there was a lot of dancing.” In any case, it appears to have been short-lived.
Nina Agdal
Leo may prefer to keep his personal life as private as possible, but he hasn’t had much success concealing his trysts or friendships from the paparazzi. When he was seen with Nina Agdal, a Sports Illustrated model who was 21 at the time, Nina quickly tried to clear the air by saying they were just friends. She claimed the much older actor never made a move on her, but given how he reacts to publicized girls, that may not be entirely true.
Roxy Horner
Leo met Roxy as his previous relationship was dissolving, which is never a good time to start a new romance. Despite the fact that she became a part of his turbulent romantic life, Roxy Horner denied rumors about their first meeting. They were spotted again months later, looking less like friends and more like love interests. Whatever the rumors said, Horner maintained that they were simply friends and that any reports of more were false.
Chelsey Weimar
Leo appeared to be having difficulty finding a partner with whom he could have more than a fling in 2016. One of his brief romances was with Chelsey Weimar, who was around 19 at the time. Though neither of them made their relationship public, they were seen having dinner together, and some of Weimar’s Instagram posts were undoubtedly taken at Leo’s house in Los Angeles. His Dutch involvement was going to be brief.
Ella Ross
There’s a chance that 2016 was simply Leo’s year of British models. Ella Ross appeared to be looking for an upgrade after being linked to Scott Disick, at least when it came to finding someone who had earned their celebrity. When they were spotted dancing close to one another at a star-studded party, neither Leo nor Ella had waited for the dust to settle after their previous relationships had ended.
Victoria Robinson
Victoria Robinson, then 23, was one of the few other brunettes Leo had spent time with since his big Hollywood break so many decades ago. His time with Robinson, like many of his other relationships at the time, was merely a fling. The first rumors that they were dating surfaced when Robinson and DiCaprio were seen leaving one of Justin Bieber’s parties in spring 2016, though the relationship never took off.
Lorena Rae
Lorena Rae, the 23-year-old German, stood out from the rest of Leo’s ladies when she appeared on the scene. No, she’s still a model, as evidenced by her petite frame, but she’s one of the few brunettes he’s stepped out with in recent years. Their romance appeared to begin around August 2017, but while he was courting her, he was also having fun with his ex, Toni Gurrn. Needless to say, it was short-lived.
Ela Kawalec
When things fell apart with both of his previous girlfriends, Leo set his sights on the Polish model Ela Kawalec. In recent years, it appears that Leo’s strategy for attracting new girlfriends has been to take them for a spin around New York City, often using the city’s bike share program, Citi Bike. In terms of Leo’s girlfriends’ careers, Ela was still a rising model, despite the numerous beachside photoshoots she’d landed.
Kristen Zang
When it comes to Leo’s love life, Kristen Zang may be the ex to end all exes. Leo was so taken with this particular blonde model that he took her to the Romeo+Juliet premiere in 1997. Unfortunately for the rising star, they’d already broken up by the time Titanic reached the top of the charts. Some say Zang is “the one that got away,” but there could be bigger loves in Leo’s life.
Bridget Hall
Leonardo DiCaprio may have achieved heartthrob status when he was only 20 years old, but he’s still embarking on romances with some of the world’s most beautiful models more than two decades later. Leo’s fascination with models began at a young age when he proudly introduced Bridget Hall as his first public girlfriend in 1994. Unfortunately, their puppy love did not last. So, which leading lady is truly his true love?
Juliette Perkins
Leo may have realized that rekindling a romance with an ex or having an affair with Lorena Rae were not the best choices for him. While looking for a woman to call his one and only, he was introduced to Juliette Perkins, who set many tongues wagging. Juliette is one of the youngest girls Leo has dated since his adolescence, but that didn’t stop them from attending several parties together.
Brittany Daniel
Leo had a new female co-star with whom he could be romantically linked when he began filming The Basketball Diaries in 1995. It’s no surprise that the young heartthrob was all over the news for his romantic ties as Leo’s profile as an actor continued to rise. Neither Leo nor Brittany Daniel ever confirmed their relationship, but given their on-screen chemistry, there’s a chance the two had a fling while working on the film.
Paris Hilton
Dating a socialite isn’t normally Leo’s style, but in 2000, Paris Hilton and Leonardo DiCaprio found themselves in the same social circles. While sharing friends is not a requirement for a romantic relationship, Paris and Leo began showing up at the same place at the same time frequently enough that rumors began that the two of them were involved. Of course, it didn’t take long for Leo to progress to bigger and better things.
Camila Morrone
Leo appears to have found the romantic bliss he’s been looking for, as he publicly announced his relationship with the young model Camila Morrone. He hadn’t had a relationship that lasted more than six months before meeting the 21-year-old, who was born the year Titanic was released in theaters. Could Camila be the right girl for Leo? Is it possible that someone else has always been waiting in the wings?
Kate Winslet
While Leonardo DiCaprio and Kate Winslet have maintained that they have never been in a romantic relationship, their long-standing friendship shows that they have been one of the most stable presences in each other’s lives for the past two decades. While Leo has moved from model to model, Kate has had three separate marriages, but their love for each other has never wavered. Maybe their love lives have never settled because they’ve always been waiting for each other.
