Leonardo DiCaprio is one of the most prolific actors in the world. His captivating and memorable roles, such as Jack Dawson from Titanic, Romeo Montague from Romeo + Juliet, and Dom Cobb from Inception, have stood the test of time. Alongside his acting career, Leo has been known for his philanthropy and environmental activism, contributing to worthy charities and helping to make the world a better place.
But what some fans and journalists really get invested in are the ladies he has dated over the years. There are also women that he's been linked with, but only remained friends with. It is hard to tell if Leo will ever settle down with the right one...only time will tell.
Here are twelve women Leo has dated and eight who wouldn't dare!
20 Dated: Kelly Rohrbach
You should know in advance that most of Leo's past girlfriends have two things in common: being blonde and being models. The first for this list is Kelly, who Leo dated in 2015. The two got engaged the same year, but sadly broke things off due to their conflicting schedules.
19 Dated: Toni Garrn
Toni Garn is known for being one of Victoria's Secret's models. The two met sometime in 2013 and had a nice (and somewhat quiet) relationship for eighteen months. Like Leo, Toni has done some acting as well, in the films, Spider-Man: Far From Home and Dreamland.
18 Wouldn't Dare: Margot Robbie
These two co-starred in the critically-acclaimed movie, Wolf of Wall Street, but they have also worked on Once Upon A Time in Hollywood, signifying their incredible friendship. In interviews, they would admit how much they respected one another. We definitely want these two to work on another movie someday.
17 Dated: Erin Heatherton
Similar to Toni, Erin is another Victoria's Secret model that made Leo swoon. They were seen together from 2011 to 2012...but had to call it quits due to Leo's busy schedule. Sadly, things have been rough for Erin as of late. In early 2019, she filed for bankruptcy.
16 Wouldn't Dare: Meryl Streep
As we said, Leo has been linked with women with shocking age gaps, but we can thankfully say that he and Meryl have a decent friendship, based on a few of their collaborations, such as Marvin's Room. Plus, it would be weird for Leo to date an actress who played his fictional mother.
15 Dated: Bijou Phillips
Bijou's relationship with Leo eventually helped her get the starring role in the 1999 drama, Black and White. Even though their romantic relationship would not last long, it was incredibly important to her. Who knows what would have happened if she had not dated Leo back then?
14 Wouldn't Dare: Drew Barrymore
These two have only worked on one movie, Poison Ivy, but despite that, they look like they are pretty close. They were seen together at the 2010 Golden Globes. However, it would be impossible for these two to be together, due to different schedules and the fact that Drew has been married three times.
13 Dated: Gisele Bündchen
Leo's relationship with Gisele was one of the most impactful ones for him so far. The fact that he took her as his date to the Oscars showed how close they were. Even though their relationship lasted for a respectable amount of years, it just wasn't meant to be.
12 Wouldn't Dare: Marion Cotillard
Since these two worked on Inception, it is not hard to see how amazing their chemistry was. Marian has described Leo as handsome and would love to work with him again, it would take a lot to have them be more than friends.
11 Dated: Kristen Zang
Leo had a very successful career in the late 90s, with Romeo + Juliet and Titanic. It seemed that Kristen was going to be the one, as he took her with him to the premiere of the former movie. And yet, their relationship broke off just like that.
10 Dated: Nina Agdal
Leo might be one of the hottest celebrities to keep an eye on, but when it comes to relationships, he would rather keep things private. His relationship with model Nina was something that crumbled and he denied the relationship, despite it being confirmed. After it all ended, she stated that he would never get affectionate with her in public.
9 Wouldn't Dare: Cameron Diaz
Leo and Cameron seem like a cute couple, as they act very natural together and worked in 2002's Gangs of New York. They both have partnerships with Tag Heuer and look good on the red carpet together. However, their relationship seems more professional than anywhere near romantic.
8 Dated: Bar Refaeli
The one who has been with Leo the longest is none other than Sports Illustrated model, Bar. She and Leo had a relationship that lasted for about six years, though it was on-and-off. They were seen getting touchy-feely at a Los Angeles Lakers vs. the Oklahoma City Thunder game, and at the Berlin International Film Festival. Those were the days.
7 Wouldn't Dare: Ellen Page
Those unfamiliar with Leo's tastes in women should know that he has a habit of dating women under the age of twenty-five. While Ellen could have been someone that Leo would be compatible with, due to their time together filming Inception, Ellen came out as gay in 2014 and married her partner in 2018.
6 Dated: Naomi Campbell
Naomi is one of Leo's flings that he still has a respectable friendship with. No surprise, she is a model and they were linked in the 90s. Their relationship was quite short and it would eventually end in 1995. Nowadays, Naomi has been linked to other men...even One Direction member Liam Payne!
5 Wouldn't Dare: Claire Danes
Who wouldn't have a crush on Leo? Claire certainly did at first! According to her, Leo was apparently the prankster on set while filming Romeo + Juliet. For starters, Claire did an excellent job with her acting and it really looked like she was head over heels for her Romeo. Thankfully, years later. they still sing each other's praises.
4 Dated: Natasha Henstridge
Natasha is one of the many models that Leo has dated, and it's not hard to see why! She was originally one of his partying friends and eventually got into acting. In 1997, they were reported to have a fling going on...and then briefly dated the next year.
3 Wouldn't Dare: Kate Winslet
The chemistry between Leo and Kate is unbelievably beautiful. Titanic was the start of something spectacular, with their friendship remaining strong to this day. Their acting is so strong that it does not get in the way of their friendship when they do intimate scenes. Them being together is a possibility we like to think of a lot, but we just love them being friends.
2 Dated: Demi Moore
After her marriage to Bruce Willis crumbled, Demi eventually found solace in Leo. They had a fling in 1997. It's hard to confirm how long their relationship lasted, but thankfully it doesn't seem to affect their overall relationship. They reunited at the Golden Globe Awards in 2009 and they looked like they wanted to catch up, even though then-husband Ashton Kutcher was also there.
1 Dated: Blake Lively
It might be shocking to people, but before she married Ryan Reynolds, Blake dated Leo! They had done a lot of fun activities, such as cycling around New York City, going to Disneyland together, and bonding with koalas down in Australia. While it sounded like it was all in good fun, their relationship lasted for a short five months.
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