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The Ample Dating List of Leonardo DiCaprio

By The Hyperhive


20 December 2023

Leonardo DiCaprio dating history

©️ The Great Gatsby

Leonardo DiCaprio’s dating history, depicted in a graph, reveals a consistent pattern of him reportedly never dating women over 25. The average age of his girlfriends, spanning more than two decades and eight relationships from 1999 to 2022, is 22.9.

His most recent split with Camila Morrone, who turned 25 this year, follows the trend of previous relationships ending shortly after the partner reaches 25. Jokes about DiCaprio’s dating preferences, involving a notable age gap, have been made in Hollywood. The public is urged to scrutinize this pattern more critically and question whether it is more concerning than amusing.

Bridget Hall, 1994

Leonardo DiCaprio dating history
©️ Allure

Their relationship has been characterized as a short-lived “fling” that lasted only for a brief period. DiCaprio was 20 at the time, and the US model Bridget Hall, was 17. This happened during the early stages of his Hollywood movie career.

Naomi Campbell, 1995

Reports had circulated for quite some time about a brief romantic involvement between supermodel Naomi Campbell and DiCaprio in 1995 when she was approximately 25 and he was 21. However, neither party has officially confirmed these rumors. Despite the speculation, they maintain a close friendship.

Leonardo DiCaprio dating history
©️ Elle

Kristen Zang, 1995-1999

During their early 20s, Kristen Zang had an on-and-off relationship with DiCaprio that spanned four years. Last year, she authored an essay for People magazine in which she criticized “ageist” headlines surrounding his breakup with Camila Morrone. Currently, she resides in Oregon with her husband.

Leonardo DiCaprio dating history
©️ Kristen Zang / Instagram

Helena Christensen, 1997

Although the two were romantically linked, neither of them ever officially confirmed their relationship. But DiCaprio was frequently seen socializing with Danish model Helena Christensen in his early twenties. She was 29 at the time. This was right after the monumental success of the 1997 classic Titanic.

©️ Eurotrash / YouTube

Amber Valletta, 1998

The two briefly dated in 1998 when they were both approximately 24 years old. According to US Weekly, DiCaprio reportedly requested his management to trace US model Amber Valletta after coming across her photograph in a magazine.

Leonardo DiCaprio dating history
©️ Instagram / ambervalletta

Bijou Phillips, 1998

Bijou Phillips, the daughter of The Mamas and The Papas singer John Phillips, briefly dated the rising Hollywood star Leonardo DiCaprio in 1998 when she was 18. Crediting DiCaprio with connecting her to director James Toback, she secured a role in his 1999 film Black and White. After parting ways with DiCaprio, Phillips went on to date her co-star Elijah Wood.

Leonardo DiCaprio dating history
©️ bijouphillips / Instagram

Gisele Bundchen, 2000-2005

DiCaprio and Brazilian supermodel Gisele Bundchen, who was 20 at the time, shared a high-profile relationship that endured for five years. The couple made a notable appearance together at the 2005 Oscars and were frequently seen attending basketball games. When they decided to part ways, Bundchen was 25, and DiCaprio was 31. Speaking to Access Hollywood, she expressed, “We were simply not meant to be in a romantic relationship, but I hold great respect for him, and I wish him nothing but the best.”

©️ gisele / Instagram

Bar Refaeli, 2005-2011

The on-again-off-again romance between DiCaprio and Israeli supermodel Bar Refaeli lasted nearly six years, concluding when she was 25 and he was 36. Their initial encounter took place at a Las Vegas party in November 2005, when Refaeli was 20 years old. However, the relationship came to an end as neither of them felt ready to settle down.

Leonardo DiCaprio dating history
©️ barrefaeli / Instagram

Anne Vyalitsyna, 2009

Marie Claire reported that during a six-month break from his relationship with Refaeli, DiCaprio briefly dated the Russian-American model Anne Vyalitsyna, who was 23 years old at the time.

Leonardo DiCaprio dating history
annev / Instagram

Blake Lively, 2011

Blake Lively, known for her role in Gossip Girl, crossed paths with DiCaprio at the 2011 Cannes Film Festival when she was 24, and he was 36. Reports suggest that they began dating after Lively auditioned for the role of Daisy Buchanan in the 2013 film The Great Gatsby. Although the part eventually went to Carey Mulligan, Lively, and DiCaprio were romantically involved for five months. Lively is now happily married to Ryan Reynolds, with whom she has three children and is expecting a fourth.

Leonardo DiCaprio dating history
©️ blakelively / Instagram

Erin Heatherton, 2011-2012

US model Erin Heatherton and DiCaprio were in a relationship for a duration of 10 months from 2011 to 2012. Unfortunately, after nearly a year together, the couple decided to part ways, citing the actor’s demanding work schedule as a contributing factor. Heatherton was 23 years old at the time, while DiCaprio was approximately 37.

©️ erinheathertonlegit / Instagram

Toni Garrn, 2013-2014

German model and actor Toni Garrn, who was 21 at the time, was in an 18-month relationship with DiCaprio, who was 39, from 2013 to 2014. However, reports indicate that she ended the romance after he was allegedly spotted clubbing in Miami with 20 other women. Rumors of a rekindled relationship surfaced in 2017 when they were photographed holding hands during a night out in New York. Nevertheless, it seemed to be a brief resurgence.

©️ tonigarrn / Instagram

Rihanna, 2015

DiCaprio and Barbadian singer Rihanna were frequently seen together in public throughout 2015, leading to speculation about a possible romance. Despite the rumors, neither DiCaprio nor Rihanna confirmed whether they were dating. If indeed they were romantically involved, Rihanna, who was 27 in 2015, would have been the second oldest woman DiCaprio publicly dated. The nature of their relationship remains unclear. Rihanna is currently in a relationship with A$AP Rocky, with whom she shares a son.

©️ badgalriri / Instagram

Kelly Rohrbach, 2015

At the age of 25, US model Kelly Rohrbach was in a relationship with DiCaprio for several months. However, according to US Weekly, they mutually decided to part ways, citing “intense work schedules” on both sides as the reason for their breakup.

©️ kellyrohrbach / Instagram

Laura Whitmore, 2016

Following the 2016 Bafta Awards, ex-Love Island host Laura Whitmore was spotted on a night out with DiCaprio. Reportedly, they were seen exchanging whispers at an after-party held at the Rosewood Hotel in London. Whitmore, who was 31 at the time, would have been the oldest woman DiCaprio romantically pursued. Despite the connection, they did not pursue a deeper relationship, as Whitmore was dating musician Rory Williams at the time.

©️ thewhitmore / Instagram

Nina Agdal, 2016

Reportedly, DiCaprio began dating Danish beauty Nina Agdal in July 2016 when she was 24. Despite embarking on multiple vacations together, including trips to New York, the Bahamas, and Montauk, the couple decided to part ways in May 2017.

©️ ninaagdal / Instagram

Camila Morrone, 2017-2022

Their relationship gained attention after being spotted together at Coachella and enjoying multiple vacations. DiCaprio crossed paths with actor Camila Morrone in December 2017, when she was 20 and he was 43. They made their red carpet debut at the 2020 Academy Awards. When questioned about their 23-year age gap in 2019, Morrone expressed to the Los Angeles Times, “There’s so many relationships in Hollywood — and in the history of the world — where people have large age gaps. I just think anyone should be able to date who they want to date.” Speculation arose about DiCaprio considering marriage, but the couple eventually parted ways two years later when Morrone was 25.

©️ camilamorrone / Instagram

Gigi Hadid, 2022

Following his split from Morrone, DiCaprio was romantically linked to US supermodel Gigi Hadid, who is 27 years old. A source quoted by Page Six mentioned that while they had a strong liking for each other, neither was seeking anything serious. The source explained, “Gigi doesn’t have the energy to run after DiCaprio. His routine is too much for her.” However, reports indicated that their connection was merely a short-lived fling.

©️ gigihadid / Instagram

For the moment, he is not dating anyone. We have been resting ever since. But we can not help but wonder, who’s next?

You might also want to read: Leonardo DiCaprio’s New Girlfriend Younger Than the Titanic Movie

The Hyperhive

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