Leonardo DiCaprio, Hollywood’s biggest stars has always been a charming and successful man; therefore he never fell short of the world’s most beautiful ladies in his company. He’s a well-known lover of sexy models, and his dating history doesn’t lie. It is difficult to know the actual number of Leonardo DiCaprio girlfriends & his dating history he had with the ladies, however we have shortlisted the list of Leonardo DiCaprio girlfriends which made headlines round the world.
Table of Contents
Here Is The List Of Leonardo Dicaprio Girlfriends And Dating History:
Bridget Hall (1994):
Leonardo DiCaprio very first girlfriend Bridget Hall, a fashion model and actor dated in the year 1994 and had breakup with him after a disappointing ‘night of love’.
Naomi Campbell (1995):
Another Leonardo DiCaprio girlfriend is Naomi, a Fashion designer, Television producer, Fashion Model, Model, and a Supermodel. Naomi and Leo were considered to be good friends. However Leo was sometimes seen flirting with Naomi in the year 1995.
Brittany Daniel (1995):
Though for not a long time, but these two love birds, shared some screen space together in 1995 film The Basketball Diaries with Brittany’s character left him seduced.
Kristen Zang (1996-1998):
This relationship lasted for around two years 1996 to 1998 and is considered as one of the most serious affairs Leo ever had. According to Leo she was the cutest girl he had ever seen. Kristen after Leo’s success of Romeo+Juliet, used to catch up with him at the sets of titanic.
Claire Daniels (1995-1996):
The duo’s outstanding performance, made them fall in love in reality to! However the Romeo+Juliet stars could not carry on the relationship for long as Leo was kind of immature for Claire, which led to their breakup.
Kate Winslet (1997):
The chemistry of Leo and Kate was the most remembered romance ever! The movie spread the magic deeply in the hearts of the people, therefore speculations were made of both of them being in love with each other, however, the truth was which was difficult to swallow by the people, that they were just good friends.
Helena Christensen (1997):
Another Leonardo DiCaprio girlfriend Helena in the queue, the affair emerged in 1997 post-Titanic, however after a few months it all ended.
Bijou Phillips (1998):
Bijou Philips was Leo’s teenage love. The relationship emerged in 1998, but didn’t last for long later she moved on with Elijah Wood.
Eva Herzigova (1998):
Yet another Victoria’s secret model, Leo and Eva both met at a premier party, however the relationship ended when the model got married.
Amber Valletta (1998):
Amber, a Spokesperson, Model and Actor, this pretty girl in magazine, who made millions of men crazy for her, got hooked to the very charming Leonardo DiCaprio in 1998.
Gisele Bundchen(2000-2005):
Yet another Leonardo DiCaprio girlfriend, the Duo was awarded with the tag of being the most beautiful couple. However the relationship was extremely fluctuating but everything was called off when Leo failed to gather the guts to propose her. Leo and Gisele ended a relationship agreeably after five years as official boyfriend and girlfriend.
Bar Refaeli (2005-2011):
Another Victoria’s secret model, who got hooked up after meeting Leo in a party thrown by U2 in the year 2005 at Las Vegas. Leonardo DiCaprio and Bar Refaeli dated each other on-and-off for over 5 years.
Emma Miller (2011):
After a detachment from Bar Rafaeli, the duo was seen hanging out together.
Ashley Roberts (2009):

The singer’s romance with the handsome actor didn’t last for long.
Anne Vyalitsyna:
Victoria’s secret model Anne met Leo in Ibiza where the couple started hanging out.
Blake Lively (2009):
It just happened for five months and yet another break up! Everybody expected this lady to change the course of Leo’s romancing life; however it was yet another failure.
Alyce Crawford (2011):
This Swimwear model from Australia made to the romancing list of Leonardo DiCaprio girlfriends, however proved to be yet another history! The duo was dating in 2011 when Leo was in Sydney filming The Great Gatsby.
Erin Heatherton(2011-2012):
Leonardo DiCaprio was in a relationship with Erin Heatherton. The relationship lasted for 10 months and ended without giving a proper reason.
Madalina Ghenea (2011):
Yet another failed relationship and tried to be known for her choice of work and not for being somebody’s past.
Toni Garrn (2013-2014):
Another Victoria’s secret model Toni, which made it possible to get the perfect woman he ever dreamt of, however the expectations were all shattered when the duo split.
Kelly Rohrbach (2015-2016):
One more Victoria’s secret model added to the list of Leonardo DiCaprio girlfriends. The 25 year old who is a model became the latest lady love for Leo. However the couple could not carry it further and called of the relationship.
Lauren Hutton (Feb 2016):
After Leo won his first ever Oscar, it is said that he celebrated his win with Lauren Hutton. They both stayed together for the whole night.
Rihanna (2015-2016):
In 2015 (maybe), January 2016 (perhaps) and again in April 2016:
Speculations are made for both the super-stars to be together. Shocking indeed!
To every body’s amazement, after multiple relationships with the leading beauties of the world, Leo hasn’t married!!