Leonardo DiCaprio’s Wild Love Life Of The Past Two Decades

By: Emma Roberts | Last updated: Aug 06, 2023

The world fell in love with Leonardo DiCaprio when Titanic was released. Women everywhere swooned over the young heartthrob who started dating models. 

But for his biggest hit, he chose to have only one woman by his side – his co-star Kate Winslet. Leo has since been linked to several supermodels, but the question remains – who has captivated the star’s heart?

Leo and Bridget: A Love Story of the Ages 

From the tender age of 20, Leonardo DiCaprio has been inspiring hearts and captivating the world with his romantic exploits. With Bridget Hall as his first public love affair back in 1994, it’s clear that Leo’s penchant for models began early. 


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But who is truly the love of his life? With an illustrious dating history featuring some of the most beautiful models in the world – a mystery that continues to linger. What is certain is that Leonardo DiCaprio’s love story is one for the ages.

Leo and Brittany: The On-Screen Romance that Captivated Fans! 

With the release of The Basketball Diaries in 1995, Leo’s stardom skyrocketed, and so did the rumors of a romantic connection with his female co-star, Brittany. 


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Though the two never confirmed their relationship, their on-screen chemistry was undeniable, sparking speculation that a real-life romance had blossomed. Fans were captivated by the possibility of Leo and Brittany being an item, and the mystery remains to this day!

Claire Danes' Teenage Crush on Leonardo DiCaprio 

From her recent confessions, it’s clear that Claire Danes had a teenage crush on her co-star, Leonardo DiCaprio. Rumors about their on-set relationship run wild, ranging from claims of unprofessionalism to the possibility of nothing happening at all. 


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Despite being 16 at the time, Danes admitted she had a special admiration for 22-year-old Leo while filming their iconic roles in Romeo + Juliet. While the truth remains a mystery, one thing is for certain: Claire Danes’ teenage heart was taken by the famous actor.

A Match Made in Heaven: Leonardo DiCaprio and Helena Christiansen's '97 Romance

In 1997, Leonardo DiCaprio was quickly rising in the Hollywood ranks as one of the biggest stars around. But one star shone a little brighter than him – her name was Helena Christiansen, one of the most iconic Victoria’s Secret models. 


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Sparks flew between the two, and soon they were seen attending multiple parties together. Though never officially confirmed, it was clear that something special was blooming between the two. Could this have been a match made in heaven? Only time will tell.

Leo's Love Life in the '90s: Experiments with Naomi Campbell! 

In 1995, Leo was still climbing his way up the Hollywood ladder, but one thing he had mastered was finding the top names on the runway. 

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Rumors swirled that Leo and Naomi Campbell had a brief fling, a totally normal thing for someone in their twenties. Even now, Leo seems to have kept some of that adventurous spirit alive in his love life. Whether it’s true or not, it’s clear that Leo was no stranger to experimenting in the ’90s.


Leo's "One That Got Away:" Kristen Zang 

Once upon a time, Leo DiCaprio and Kristen Zang shared a fairytale romance. The model and actor were head over heels for each other, so much so that Leo took her to the premiere of his movie, Romeo+Juliet

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By the time his career skyrocketed with Titanic, they had parted ways. Many say that Kristen Zang was Leo’s “one that got away,” but who knows – he may have even bigger love in his life now!


Leonardo DiCaprio's Unfortunate Romance with Demi Moore

Leonardo DiCaprio’s love life has been quite a rollercoaster. After a few outings with Demi Moore, it seems he had a taste of what it’s like to date an older woman. But, far from being smitten, Leo appeared to be less than enthused. 

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While Moore may have been looking for a younger man post-split from Bruce Willis, it was clear that DiCaprio was not meant to be that man. Could it be that the age gap was too much to handle?


A Short-Lived Romance: Leonardo DiCaprio and Natasha Henstridge 

Leonardo DiCaprio and Natasha Henstridge’s relationship may have been brief, but it was certainly an interesting one. At the time they were introduced, Leo was on the brink of becoming an A-list star due to the success of Titanic, while Natasha had just begun to transition from modeling to acting. 

Source: Pool BENAINOUS/DUCLOS/Gamma-Rapho via Getty Images

Although they never officially confirmed their relationship, it was clear that the two were quite fond of one another. Unfortunately, their ambitions kept them apart, and the romance was not meant to last.


The Unconventional Relationship of Leonardo DiCaprio and Bijou Phillips

As a young man, Leonardo DiCaprio wasn’t afraid to be daring in his choice of women. His relationship with Bijou Phillips in the 1990s was no exception. 

Source: Getty Images Photo by Ron Galella, Ltd.

Despite her not being the type of tall, blonde model he’d go for later on, it was Leo who connected her with the director who cast her in her debut film, Black and White. Thus, this unconventional relationship may have been short-lived, yet it certainly proved to be beneficial to both parties.


Leo's Rocky Road to Love 

Leo DiCaprio seemed to always have a new model in his life, but when he was introduced to the gorgeous Eva Herzigova at the film premiere of The Man in the Iron Mask in 1998, he knew he’d have to pursue her. 

Source: William STEVENS/Gamma-Rapho via Getty Images

Even with his star status, their relationship was short-lived – like many other flings since his rise to fame. Leo was on a rocky road to love, and it wouldn’t be long before he moved on to the next one.


A Look Back at Leo's Romance with Kidada Jones, Daughter of Quincy Jones! 

In the late 1990s, photos of Leonardo DiCaprio and Kidada Jones circulated, sparking speculation that the two might have been romantically involved. While neither confirmed the relationship, it’s possible Leo and Kidada had a brief fling before he started dating Gisele Bundchen. 

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For Kidada, being linked to Leo was just one of the many highlights in her life following her engagement to the late rapper Tupac Shakur. Take a trip down memory lane and revisit this exciting era in Leo’s life!


Leo DiCaprio & Trishelle Cannatella: A Rumoured Romance? 

Remember Trishelle Cannatella, one of the first reality stars to make waves with the public? Well, the rumors have it that she caught the eye of Hollywood’s heartthrob, Leo DiCaprio! 

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During what must have been an off period with Gisele, Leo was linked with Trishelle, but with him being in a relationship, we only have the latter’s word for it. Could this be true? Was the legendary actor smitten with the reality star?


Leo and Paris: The Unforgettable Romance 

Leonardo DiCaprio and Paris Hilton, two of Hollywood’s most sought-after stars, had the world in a frenzy in 2000. Rumors were flying that the socialite and the A-lister were an item, even though it wasn’t Leo’s usual style. 

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They were seen in the same circles, and it seemed like they were inseparable. But, as quickly as the romance had bloomed, it was over, and Leo had moved on to bigger and better things. The Leo and Paris whirlwind romance surely left a lasting impression!


Leo and Gisele: A Love That Couldn't Last 

Once upon a time, the world believed that the talented actor Leo had finally found his true love in the beautiful Gisele Bundchen. For five blissful years, Leo and Gisele were inseparable, even accompanying each other to the Oscars. 

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Sadly, it was not meant to be, as the couple eventually parted ways. Gisele moved on to marry Tom Brady, while Leo remains single. It seems like the magical love story of Leo and Gisele was doomed from the start.


Leo's Wild Ride: From Gisele to Bar Refaeli 

After his split with Gisele, Leo’s wounds were still healing when he met Bar Refaeli at a Sports Illustrated party in Las Vegas. The two embarked on a wild ride of on-and-off romance from 2005 to 2011. 

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Though their relationship never reached the same heights as his previous one, Leo and Bar were a couple to be reckoned with. In the end, the two parted ways for good, leaving Leo to find his next love.


The Glamorous And Short-Lived Romance of Leonardo DiCaprio & Anne Vyalitsyna 

Amidst a breakup, Leonardo DiCaprio found himself single enough to pursue a brief fling with a world-famous model. Russian-born Anne Vyalitsyna had graced the pages of Sports Illustrated and walked the runway for Victoria’s Secret. 

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The two were seen together in various glamorous locations like Ibiza. However, unknown to Anne, Leo still had feelings for another woman, ultimately leading to the couple’s split. It was beautiful but an all too fleeting romance.


Leo's Dream Come True: Blake Lively 

When Leo’s gaze fell upon the beautiful Blake Lively, he knew he had found his dream girl. With her long legs and golden hair, she looked like the girl of his dreams. But when they got closer, he soon realized that she was a lot different from any other girl he had ever dated. 

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Blake was happy to cook and bake for Leo, an experience he had never had before. He was mesmerized by her beauty and her kind and generous heart. Leo had certainly found a special someone in Blake Lively!


Madalina Ghenea: The Romanian Beauty Who Stole Leo's Heart! 

After his split from Bar Rafaeli, Leo DiCaprio had a short-lived romance with the stunning Madalina Ghenea. The brunette beauty was spotted canoodling with the actor at his Sydney home while filming The Great Gatsby

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Not only did this cause a stir in the U.S. but also back in Madalina’s home countries of Romania and Italy. Fans couldn’t get enough of their beloved star being linked to Hollywood’s ultimate heartthrob – it was a match made in heaven!


What's the Truth Behind Leo and Alyce's Relationship? 

Rumors have been swirling for years about the relationship between Academy Award-winner Leonardo DiCaprio and Australian model Alyce Crawford. While the model insists their connection was never more than platonic, sources claim to have spotted Crawford frequently visiting DiCaprio’s hotel in 2011 when he was filming The Great Gatsby

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With Leo going through a turbulent romantic period at the time, anything could have happened between the two. Were they just friends, or was something being kept from the public?


Love Story of Leo and Erin - A Victoria's Secret Fairytale 

Leo and Erin had a love story worthy of a fairytale! After a brief fling with an actress, Leo got back to his preference: models. He found his match in Erin Heatherton, a Victoria’s Secret model. 

Source: Chance Yeh/Patrick McMullan via Getty Images

They enjoyed spending time together and made things work for a year between 2011 and 2012. Despite their crazy schedules, they managed to make it last until they eventually parted ways after 10 months. A beautiful love story that ended too soon!


Leo and Miranda's Secret Romance? 

Did Leo and Miranda Kerr have a secret romance? Rumors began to swirl in 2012 about the two being linked in several publications while Kerr was still married to actor Orlando Bloom. 

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After the couple announced their breakup in 2013, people began to wonder if Kerr’s alleged fling with Leo was a factor. While we may never know what really happened between them, one thing is for sure – Leo and Miranda Kerr’s relationship was a topic of intrigue!


Leo DiCaprio's Short-Lived Romance with French Model Margarita Gauchet 

It was 2012, and Leo DiCaprio had a break from his usual blondes when he was seen getting cozy with French model Margarita Gauchet on a yacht. But despite their public kiss, this romance appears to have been even more short-lived than usual. 

Source: Reddit.com

Little has been shared about the relationship, and neither of them has denied that it happened, yet it’s clear it didn’t work out. Who knows what could have been had this tryst taken a different path?


Leo DiCaprio and Kat Torres: A Short-Lived Romance 

Leo DiCaprio had his sights set on Brazilian model Kat Torres when they ran into each other at Cannes in 2013. Though they looked good together, the chemistry between them was lacking. 

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It was also likely that DiCaprio had another woman to whom he was more devoted. To make matters worse, Torres was quick to share details of their relationship with the public. Unfortunately, the relationship between Leo and Kat was short-lived and ended soon after it began.


Healing a Broken Heart: Alesia Riabenkova's Tale 

Alesia Riabenkova found herself in the spotlight for the wrong reasons when wild claims of being attacked by a photographer, which couldn’t be verified, started making news. Following a very public breakup with a Scottish actor, rumors spread that Alesia was seeking solace in the arms of Leonardo DiCaprio. 

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But it was her own strength that helped her cope with the aftermath of the painful breakup, rather than the company of a Hollywood superstar. Alesia’s story is a reminder that breakups can be difficult, but with the right support, we can all heal a broken heart.


Leo and Garrn: A Love Story That Couldn't Last 

Throughout his storied career, Leo DiCaprio has been linked to many beautiful women, but his relationship with German model Toni Garrn proved to be the most enduring. 

Source: Gisela Schober/German Select for Mercedes-Benz/Getty Images

After their first meeting in 2013, the pair went on and off for the next four years, even briefly reuniting in 2017. Sadly, it wasn’t meant to be, and the two eventually parted ways. Although Leo’s love life may not have worked out, his acting career is still going strong.


Katie Clearey: From 'Iron Man 2' to Leo DiCaprio

Katie Cleary has come a long way since her days as an established actress in franchise films like Iron Man 2. After filing for divorce from her husband, Katie was spotted with Leo DiCaprio at a party, and it became the talk of the town! 

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People speculate that Leo might have been the final push that ended her marriage. It’s clear that Katie didn’t need Leo to further her career, but it was a great choice to move on from a failing marriage.


Did Leo and Rihanna Have a Secret Romance? 

For a while in 2015, the rumor mill was abuzz with whispers of a secret romance between Leo and Rihanna. The two were often spotted together at various parties, with Leo rarely seen without a hat pulled low over his face. 

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However, neither ever confirmed a relationship between them and it was later revealed that Rihanna had actually been in a relationship with one of Leo’s friends. Did Leo and Rihanna have a secret romance? Only they know the truth.


Another One Bites The Dust: Leonardo DiCaprio and Kelly Rohrbach Split 

The sparks between Leonardo DiCaprio and Kelly Rohrbach were clear for all to see as the two were spotted out and about in New York City. But, just like the other models before her, it seemed the flame between this couple died out. 

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After months of speculation, the couple announced their split, proving that Leo’s romantic history is still very much intact. The superstar’s latest romance has come to an end, leaving us all to wonder who his next leading lady will be.


Leonardo DiCaprio's "Fun" Encounter with Laura Whitmore 

Leonardo DiCaprio’s love life has been a source of endless fascination over the years. Recently, eyebrows were raised when the Hollywood actor was spotted cozying up to Irish television presenter Laura Whitmore at an award show after-party. 

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Whitmore remained coy when asked about her relationship with Leo, simply stating, “Everyone was just having fun—there was a lot of dancing.” Whatever the case may be, it appears the romance was short-lived.


Leo's Not-So-Private Love Life: Just Friends or More?

Leonardo DiCaprio is an enigma when it comes to his personal life, but the paparazzi always seem to find him. Recently, they caught him with a 21-year-old Sports Illustrated model, Nina Agdal. 

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While Nina was quick to say they were just friends, Leo’s past reactions to girls who go public suggest there might be more to the story. Is Leo’s relationship with Nina just platonic, or is there something more? Only time will tell!


Sparks Fly as Leo and Roxy Ignite Rumors of Romance 

Leo and Roxy’s first meeting came at a tumultuous time for him, as his last relationship was ending. Despite the rumors swirling about their connection, Leo denied any romantic involvement. 

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But months later, the two were spotted together, looking more like love interests than friends. Despite the speculations, Leo insisted that they were just friends and that any reports of a relationship were false.


Leonardo DiCaprio's Short-Lived Romance with Chelsey Weimar 

Leonardo DiCaprio’s love life has been the source of much speculation over the years, and back in 2016, it was no different. Rumors began to swirl when Leo was spotted dining with Dutch model Chelsey Weimar, who was around 19 or 20 years old. 

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While neither made an official statement, Weimar’s Instagram posts, taken at Leo’s Los Angeles home, confirmed that the two were more than just acquaintances. Sadly, Leo’s romance with Weimar was short-lived.


Leo & Ella's New Romance - Sparks Fly at Star-Studded Party! 

The end of 2016 was a time of new beginnings for British model Ella Ross and Hollywood heartthrob Leo. After being linked to Scott Disick, Ella seemed to be looking for an upgrade, and it looks like she got it! 

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The two were spotted getting close at a star-studded party, not wasting any time after their previous relationships ended. 


Leo DiCaprio's Short-Lived Romance with Victoria Robinson 

When Leo DiCaprio rose to Hollywood stardom decades ago, he only had eyes for one woman – Victoria Robinson. At 23, Robinson was one of the few brunettes to spend time with the actor. 

Source: Reddit.com

Their relationship, however, was short-lived and only lasted as far as Justin Bieber’s spring 2016 party. Despite the whispers that they were an item, the romance never blossomed. Could it be that Leo’s heart belongs only to the silver screen?


Leo's New Flame: Brunette Beauty Lorena Rae 

The romance between Leo and brunette beauty Lorena Rae started to spark in August 2017. At just 23 years old, the German model was different from the other ladies Leo had been seen with. 

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With her small frame and beautiful brunette locks, Lorena Rae quickly caught Leo’s eye. Despite his attempts to woo her, Leo’s relationship with the beautiful model didn’t last long as he was still happily hitting the town with his ex, Toni Gurrn. Could Lorena Rae be the one to finally win Leo’s heart?


Leo's Love Tour of NYC - Fueled by Citi Bike 

Leo’s had a rough time with relationships in the past, so he decided to give it another shot with the Polish model Ela Kawalec. With a clear agenda in mind, Leo took Ela on a tour of New York City – fueled by none other than the city’s bike share program, Citi Bike. 

Source: ela.kawalec/Instagram

Even though Ela was still an up-and-coming model with plenty of beachside photoshoots under her belt, Leo was determined to make this relationship work. Who knows, maybe their love tour of NYC will be the start of something beautiful!


Young Love Finds Leo: 19-Year-Old Juliette Perkins Sets the Gossipers Abuzz

After a few failed attempts at finding love, Leonardo DiCaprio has finally found his one and only! Rumors have been swirling about Leo’s relationship with the 19-year-old Juliette Perkins, whom he has been spotted leaving parties. 

Source: Rich Fury/Getty Images

Although Leo is 41, his age gap with Juliette has not been an obstacle for them, proving that love knows no bounds. Is Leo settling down and leaving his bachelor days behind? 


Is This Leo's Happily Ever After? 

After years of searching, Hollywood heartthrob Leonardo DiCaprio may have finally found his happily ever after. 

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Before this, Leo hadn’t had a relationship lasting longer than six months since his last love, Erin Heatherton, in 2012. Unfortunately, Leo and Camila have called their romance quits after four years. 


Waiting for Love: The Enduring Bond Between Leo and Kate 

For the past two decades, Leonardo DiCaprio and Kate Winslet have remained steadfast friends, supporting each other through the ebbs and flows of their love lives. While Leo has been in-and-out of relationships, Kate has tied the knot three times. 

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Yet, their loyalty to one another has never faltered, making us question if they were waiting to be together all this time. Truly, their friendship is a testament to the power of love.