Leonardo DiCaprio may have achieved heartthrob status when he was barely 20 years old, but more than two decades later, he’s still embarking on romances with some of the most beautiful models in the world. So which one of them is truly the love of his life? Let’s find out.
Brittany Daniel
When Leo began filming The Basketball Diaries in 1995, he had a new female costar to whom he could be romantically linked. As Leo’s profile as an actor continued to rise, it’s no surprise that the young heartthrob was all over the news for his romantic ties. Neither Leo nor Brittany ever confirmed their relationship, but considering their on-screen chemistry, there’s some possibility that the two had a fling while they were working together on the film.
Claire Danes
Claire Danes may have a high-profile husband of her own nowadays, but back when she was a teenager, she was the on-screen love of Leonardo DiCaprio. The rumors about their on-set relationship run the gamut. Some sources claim that though Claire was only 16, she found 22-year-old Leo unprofessional. That’s a stark contrast to her recent confession that she had a crush on him while they were filming Romeo + Juliet. Danes implies nothing happened, but it’s hard to know for certain.
Helena Christiansen
As Leo’s career ramped up in the mid-1990s with hits like Romeo+Juliet, it was only natural that he searched for the biggest names at the Victoria’s Secret Fashion Show. Helena Christiansen may be one of the best known Angels, even today, but back in 1997, she was possibly even a bigger name than Leonardo DiCaprio himself. He may not have ever made things public, but it was pretty clear something was going on based on the number of parties they attended together.
Naomi Campbell
Leo may not have hit peak movie star back in 1995, but he certainly knew how to find the biggest names on the runway, even when he was just hitting adulthood. Though he and Naomi Campbell never seemed to have a serious relationship, the rumor back in the day was that the two enjoyed some sort of fling, at least for a brief period of time. At that age, it’s normal to experiment with your love life, though it seems Leo hasn’t quite left those days behind.
Kristen Zang
If there is one ex to end all exes when it comes to Leo’s love life, it very well may be Kristen Zang. Leo was so enamored of this particular blonde model that he even took her to the premiere of Romeo+Juliet back in 1997. Sadly for the star on the rise, by the time he really topped the charts with Titanic, they’d already broken up. Some say that Zang is “the one that got away,” but then again, there may be bigger love in Leo’s life.
Demi Moore
When Leonardo DiCaprio chanced an outing or two with Demi Moore, it seems he was exploring what a relationship could be like with an older woman. Far from looking as enthralled as his much younger girlfriends look with him these days, young Leo looks a little bit like he’s suffering with the more worldly Demi. Even if she was on the hunt for a younger man following her split from Bruce Willis, it’s clear that Leonardo DiCaprio was not that man.
Natasha Henstridge
Natasha Henstridge may not have been the first model Leo was linked to, but given her acting ambitions, it’s no wonder the relationship wasn’t built to last. Around the time Leo and Natasha were introduced to one another, Leo was on the brink of becoming an A-list star following the release of Titanic, while Natasha had experienced her first taste of success as an actor, rather than a model. The two never quite went public with their romance.
Bijou Phillips
It seems that as a young man, Leo was slightly more experimental when it came to his choice of women. Bijou Phillips in the 1990s wasn’t exactly the type of leggy blonde model that Leo would prefer in his later years. However, it seems their relationship, no matter how short it may have been, proved advantageous. Phillips may have come from a showbiz family, but it was Leonardo DiCaprio who connected her to the director that would cast her in her first film, Black and White.
Eva Herzigova
It wouldn’t be long before Leo moved on from his last relationship to a new one with yet another model, Eva Herzigova. He was the biggest star in the world, but when he was introduced to the Czech beauty at the film premiere for The Man in the Iron Mask in 1998, he knew he’d have to pursue a romantic relationship with her. Like many of his other flings since his rise to fame, their entanglement would be short-lived.
Kidada Jones
Back in the late 1990s, Leo was captured in several photos with Kidada Jones. If the name sounds a little familiar, it’s because her father is Quincy Jones. While the two never confirmed a romance, it’s possible that Leo and Kidada enjoyed a brief romance not long before Leo began his relationship with Gisele Bundchen. For Kidada, dating Leo was just a drop in the bucket after having been engaged to the rapper Tupac Shakur.
Trishelle Cannatella
Trishelle Cannatella might have faded into obscurity shortly after her time on The Real World came to an end, but if the rumors are true, then at least Leo DiCaprio noticed her. During what must have been an off period with Gisele, Leo was linked with one of the first reality stars to make waves with the public. Of course, given Leo’s relationship status at the time, we only have Trishelle’s word to go off of.
Paris Hilton
Dating a socialite may not be Leo’s usual M.O., but back in 2000, Paris Hilton and Leonardo DiCaprio wound up running in the same social circles. While sharing friends is not a prerequisite for a romantic relationship, Paris and Leo began showing up to the same place at the same time frequently enough that whispers began that the two of them were somehow involved with one another. Of course, it wasn’t long before Leo had moved on to bigger and better things.
Anne Vyalitsyna
During a rough patch with Bar, Leo found himself single enough to go after a model who had both graced Sports Illustrated and was a Victoria’s Secret model, the Russian-born Anne Vyalitsyna. The two shared a brief fling during Leo’s six-month break, where they were often spotted traipsing about glamorous locations like Ibiza. Little did Anne realize that another woman still had a hold on Leo’s heart, making it impossible for them to get more serious. They’d soon break up.
Madalina Ghenea
During Leo’s rocky period after splitting with Bar Rafaeli, the brunette Madalina Ghenea made an appearance on Leo’s arm for a short period of time. The two were seen canoodling at his temporary home while he was in Sydney filming The Great Gatsby. It wasn’t just Americans who were obsessed with the budding romance. Both Romanians and Italians can’t get enough of their own star, so seeing her with DiCaprio was a particularly exciting piece of news.
Alyce Crawford
Australian model Alyce Crawford still maintains that she and Leo never really dated, but considering the frequency they saw each other back in 2011 while Leo was working on The Great Gatsby, it’s hard to say if something more is just being hidden from the public. Several sources claimed to have seen Crawford going to Leo’s hotel, but that they were always cautious about being seen with one another in public. Given that Leo was going through a rocky romantic period, anything is possible.
Erin Heatherton
Following his brief interlude with an actress, Leo was happy to run right back into the arms of models, this time choosing Erin Heatherton. Erin was yet another Victoria’s Secret model that Leo enjoyed spending time with, and they managed to make things work for nearly a year between 2011 and 2012. Unfortunately, they claimed that their schedules were too crazy to keep their relationship going, and with that, they ended their partnership, roughly 10 months after they were introduced to one another.
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 officially announced their breakup in 2013, she was supposedly out and about with Leo in 2012. We may never know whether this contributed to her breakup with Bloom or if Kerr was prone to straying because she knew that a divorce was on the horizon.
