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.