Another short fling for Leonardo Dicaprio happened in the late ’90s when he was introduced to the Czech-Italian supermodel and actress Eva Herzigová at the film premiere of The Man in the Iron Mask, an underrated action drama with Dicaprio who stars in a dual role. Their fling was a short one, something that has become expected when you see DiCaprio starting up a romance with someone. It’s unclear whether Leo is the one who usually breaks up with these models and actresses or if he’s just not marriage material. We have a hunch that it’s probably the former.
Herzigová was born in the Czech Republic and began her modeling career at age sixteen after winning a beauty contest in Prague. She was married to Tico Torres, Bon Jovi’s drummer, from 1996 until a year before meeting DiCaprio. She has since gone on to have three sons and still appears in various fashion projects. The model was pictured with young Dicaprio in some pretty intimate moments when the two were together.
Trishelle Cannatella
Let's face it; if there's one type of lady that you know DiCaprio is interested in, it's artistic, young, tall blonde women with beautiful faces and perfect bodies. That might be a tall order for most guys, but when you're an A-list celebrity with one of the most recognized faces in the world, it's basically your average lady. Trishelle Cannatella, one of the actor's earlier dates, became known primarily for her appearance in the reality show "The Real World: Las Vegas," where a group of diverse strangers tries to live together in Vegas.
The actress, poker player, and Playboy model disappeared from the media's attention shortly after and has not been acting in many years. She dated DiCaprio during the height of her fame when she appeared on reality shows such as "The Surreal Life," "Kill Reality," "Punk'd," and "Fear Factor." The two eventually broke up, and we're happy to say that Trishelle Cannatella then married John Hensz.
Kidada Jones
Kidada Jones was seen in the late '90s walking in shorts with her potential boyfriend, Leonardo DiCaprio. The two allegedly began dating shortly after her engagement with rapper Tupac Shakur ended due to the tragic fact that he had been gunned down and passed away. It's possible that she was just using DiCaprio as her rebound guy in order to deal with the loss of her fiance, or maybe she actually hoped that the young actor and her would begin their own true love story. Either way, eventually, the two stopped appearing together, and DiCaprio soon began his serious relationship with Gisele Bundchen.
Jones is an actress, model, and fashion designer. Unfortunately, she has not been married or engaged since her 1996 engagement to Tupac Shakur, except for a short three-year marriage to Jeffrey Nash from 2003 until 2006. It's hard to settle after dating a guy like DiCaprio, so we can definitely understand her plight. By the way, she also dated rapper LL Cool J, also known as Sam Hanna, from the popular crime show NCIS: Los Angeles.
Bar Refaeli
One of the most public relationships that Leonardo DiCaprio had ever had was with the beautiful Israeli model Bar Refaeli. The two met at a Sports Illustrated party in Las Vegas just shortly after Dicaprio and Gisele Bundchen had broken up their (relatively) long relationship. Perhaps he was somewhat saddened by the relationship's ending and was looking for another beautiful blue-eyed model to replace his previous love with. The two dated on and off from 2005 up to 2011 before officially breaking up their relationship.
Bar Refaeli is perhaps one of the most popular people to ever come from Israel. She is the most internationally successful model to ever come out of the small country and co-hosted the media frenzy that was the 2019 Eurovision which took place in Tel Aviv, Israel. She has two children and is currently married to Adi Ezra, an Israeli billionaire who made his fortune as a businessman. Despite the relationship between DiCaprio and Refaeli being a bit rocky, it was still one of the most popular pieces of news in Israeli tabloids at the time.
Anne Vyalitsyna
Dicaprio and Bar Refaeli didn't have the most stable of relationships. In the six years they had dated, the actor had found himself with various other women that ironically looked almost exactly like his then-on-again-off-again girlfriend. One of these women was Anne Vyalitsyna, a Russian American model who is best known for appearing in Sports Illustrated Swimsuit Issues from 2005 to 2014. They were often seen vacationing in glamorous locations such as Ibiza. The two were mostly a fun fling as Leo eventually returned to Bar Refaeli.
Anne Vyalitsyna was engaged to Adam Cahan, the former Senior Vice President of Yahoo!'s mobile department, but that eventually ended, as well. She has a very interesting life that includes doing marathons and volunteering to help people with disabilities. Vyalitsyna also dated Adam Levine from 2002 to 2011 and used that connection to appear in two of his band's, Maroon 5, music videos, the most popular being "Misery."