Leonardo DiCaprio’s Relationship Through The Years – Who Has He Dated?
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Leonardo DiCaprio’s relationship is very colorful, as he is best known for his numerous flings with the ladies. The Titanic star has a history of dates with ladies who are tall and blond and have probably already walked on a catwalk. Interestingly, his relationship timeline has a cross-section of Hollywood actresses, Victoria’s secret catwalk queens, illustrated sports models, and many more.

DiCaprio was born on November 11, 1974, in Los Angeles and is the only child of his parents Irmelin and George DiCaprio. The famous actor began his acting career at the age of five and has starred in dozens of films and received numerous awards for his outstanding acting skills. His breakthrough came in 1997 after his appearance in James Cameron’s film Titanic. His impressive performance in this film earned him several awards and put him in the spotlight.

Leonardo DiCaprio’s Relationship Through The Years – Who Has He Dated?
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The acting veteran is not only a movie star but also a producer. He has produced several films, including Out of the Furnace (2013), Runner Runner (2013), and The Wolf of Wall Street (2013), to name but a few. He has worked with top stars like Ben Affleck, Justin Timberlake, Cassey Affleck, and Sam Shepard, to name a few. Leonardo DiCaprio has amassed an enormous fortune for himself and currently has an astonishing net worth of $245 million. Learn more about his relationship and dating history below.

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Leonardo DiCaprio’s Relationship Through The Years – Who Has He Dated?

1. Leonardo DiCaprio and Naomi Campbell

Leonardo DiCaprio’s Relationship Through The Years – Who Has He Dated?
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The relationship between Leonardo DiCaprio and Naomi Campbell began when Leonardo DiCaprio was a good friend for a long time. The supermodel actress met Leo in 1995. Although they kept their relationship on a platonic basis, they were seen together with their mutual friends at various events and during vacations. Campbell maintained several relationships with popular celebrities such as Flavio Briatore and Adam Clayton. She is currently involved with Louis C. Camilleri together.

2. Kristen Zang

Leonardo DiCaprio’s Relationship Through The Years – Who Has He Dated?
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Leo had a brief relationship with Kristen Zang, a famous American actress, and model. She is best known for her appearances in popular movies like Love & Sex and Hollywood. The duo began their relationship in 1996, even before Leo’s breakthrough in Titanic. Kristen is said to have dumped him in 2007 for his childishness and immaturity. Later that year, Leo also had an affair with Danish model Helena Christensen and Species stars Natasha Henstridge and Emma Bunton.

3. Bijou Philips

Leonardo DiCaprio’s Relationship Through The Years – Who Has He Dated?
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Leonardo had a short-lived romance with the amazing American model and actress Bijou Philips in 1998. She is the daughter of the famous American singer John Philips. The two ended their relationship after a few months. Philips also went out with Elijah Wood and married Danny Masterson in 2011. After their separation, Leo had a short relationship with other models that same year, including Amber Valletta and Eva Herzigova.

4. Emma Miller

Leonardo DiCaprio’s Relationship Through The Years – Who Has He Dated?
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In 2009, Leo was associated with an affair with Chelsea star Emma Miller. The duo was spotted on a dinner date in South Kensington in 2009, and after a while, they went their separate ways. In the same year, they were also associated with the amazing American singer Ashley Roberts and the Russian Victoria’s Secret model Anne Vyalitsyna.

5. Leonardo DiCaprio and Gisele Bundchen

Leonardo DiCaprio’s Relationship Through The Years – Who Has He Dated?
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It would be hard to imagine Gisele Bundchen being with anyone other than American football quarterback Tom Brady, but in the early 2000s, she had a long romance with Leonardo Dicaprio. They had a mutual relationship that began in 1999 and ended in 2005. The duo made it onto People Magazine’s list of the most beautiful couples in 2004. They went separate ways after Leo failed to ask the question. Gisele married Tom Brady in 2009. Together they have two children.

6. Leonardo DiCaprio and Bar Refaeli

Leonardo DiCaprio’s Relationship Through The Years – Who Has He Dated?
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After his separation from Gisele, Leo began another relationship with another Victoria’s Secret model named Bar Refaeli. This gorgeous model is one of the most internationally successful Israeli models. She has worked with top brands like Maxim, Elle, Harper’s Bazaar, Marie Claire, and Vogue, to name a few. Their relationship ran back and forth until 2011 when they both went their separate ways.

7. Blake Lively

Leonardo DiCaprio’s Relationship Through The Years – Who Has He Dated?
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The media city got into an uproar in 2011 when Leonardo DiCaprio’s relationship with Gossip Girl star Blake Lively came to light while snuggling up on a yacht in Cannes. The short-lived romance lasted five months before the two went their separate ways. While Blake continued to date Ryan Reynolds, Leo was looking for more models. He had an affair with the Australian model Alyce Crawford and Romanian model Madalina Ghenea while shooting The Great Gatsby in Australia.

8. Erin Heatherton

Leonardo DiCaprio’s Relationship Through The Years – Who Has He Dated?
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Leo was seen with another blonde from Victoria’s Secret, Erin Heatherton, when they toured the grounds of the historic Vaucluse House in Sydney in December 2011. The duo also took their love to the beaches of both Mexico and New York City. Their relationship lasted for about 10 months before it came to an end. Leo’s busy schedule during the shooting of The Wolf of Wall Street in 2012 dragged their relationship into the mud.

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9. Toni Garrn

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While it was over between Leo and Erin Heatherton, he was also taken with another German model, Toni Garrn. This stunning model was also working for Victoria’s Secret at the time. Despite moving in together, things didn’t really go well between the two. In November 2014 they decided to go their separate ways.

10. Rihanna

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Leonardo Dicaprio and Rihanna apparently met at a Playboy Villa party that took place after the Golden Globes 2014. The couple attended Rihanna’s cousin’s wedding in Barbados in 2015. Surprisingly, rumors began to spread that the duo was in a relationship, but Rihanna flatly denied the rumors and said she was too busy to go out with anyone. After that Leo had a brief relationship with the American model of Sports Illustrated named Kelly Rohrbach. The couple called it an exit in early 2016.

11. Nina Agdal

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Leonardo DiCaprio’s relationship with Victoria’s Secret model Nina Agdal took place in 2016. The Danish model appeared in several Sports Illustrated Swimsuit Issues and on the runway of Victoria’s Secret. The couple was spotted on vacation in Montauk, New York, and during their trip to a private island in the Bahamas in June 2017. They went their separate ways in May 2017. In the same year, Leo was also associated with Victoria Robinson and Lorena Rae.

12. Camila Morrone

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Leonardo Dicaprio’s most recent relationship is with Camila Morrone, an American actress cum model. The Argentine-born model appeared on the front page of Vogue Turkey and also worked as a catwalk model for the Moschino Resort Collection in 2017. She made her acting debut in 2013 when she appeared in the film entitled Bukowski. Her most recent project is the 2018 film entitled Death Wish, in which she starred alongside Bruce Willis. Although the duo has not publicly confirmed their relationship, they have been seen together on several occasions. We hope that things between the two will work out and not end up like Leo’s previous relationships.