Pictures Of 21 Hot Women Leonardo DiCaprio Has Dated (And Details About Their Relationships)

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21 Of The STUNNING Celebrity Women Leonardo DiCaprio Has Loved And Lost
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His love life is a TRUE work of art.

The course of true love never did run smooth... even when you have millions of dollars, a crazy amount of fame, and models at your beck and call.

The next time you find yourself going through a breakup or despairing that you'll never find true love, I want you to remember two words:

Leonardo DiCaprio.

I know what you're thinking: "Shut up, Becca! Leonardo DiCaprio is a mega-famous Academy Award winning actor known for dating a vast array of the world's sexiest women!"

That's totally true, but you know what? He hasn't found his one true lasting love connection... yet. 

RELATED: Leonardo DiCaprio & Kate Winslet Spark Dating Rumors (Again) After Super Cozy Pics Surface And 'Sources' Say They're In Love

In fact, his love life has been dramatic, sexy, and downright operatic. 

If you doubt me, check out this list of 13 of the most notable women he's dated (including the gasp-inducing rumor about who Leo's girlfriend is now):

1. Kate Moss

Back when they were both wee pups getting their start on the A-List in 1993, 20-year-old Leo and Kate spent some time together "casually" dating in New York City. 

And that's all she wrote about that...

2. Brittany Daniel 

If gossip rag The Sun is to be believed, Leo and Brittany Daniel of Sweet Valley High fame (be still my heart!) met on the set of The Basketball Diaries, at which time they claim Brittany quickly seduced Leo. Their initially sexual relationship turned into a courtship and continued even after filming stopped, but although the duo dated for all of 1994, though were seldom photographed together.

Elizabeth Wakefield would never have approved of such antics, of course, but thankfully, I am not Elizabeth Wakefield. 

3. Naomi Campbell 

Leo and Naomi had an intense and probably quite sexy affair rumored to have begun in 1995, but which fizzled after only a few months. Yet while their romantic bond was doomed, their friendship certainly wasn't. The duo is still often photographed socializing together.

Could Naomi have been the first model to stir Leo's lifelong (so far) passion for models?

Maybe. Or else it could just be that he finds models to be exquisite specimens he is able to date because he's an A-List actor — and, you know. Because he can. 


4. Kristen Zang 

Leo met Kristen right as began his ascent into teen heartthrob status in 1996. In fact, he took Kristen (a model, naturally) to the premiere of Romeo + Juliet. While at the time Leo was quoted as saying that Zang was the "love of his life", the relationship lasted only two years, ending in 1998.

Was there ever a tale of more woe? Perhaps...

5. Demi Moore

Rumor has it that at some point in 1997, following her separation from Bruce Willis and prior to famously landing much-younger-than-her Ashton Kutcher, Demi found some comfort (or, at least, some fun) in Leo's handsome arms. 

6. Helena Christensen

Once Titanic premiered in 1997, Leo really became a sexual icon to a generation of women. His fans weren't the only ones who were spellbound by the guy, either.

In one of his many rendezvous, Leo is rumored to have enjoyed a "sexy romp" (stars enjoy sexy romps nearly as much as they enjoy canoodling, btw) with supermodel of the day Christensen.

7. Natasha Henstridge 

Shortly after getting his freak on with one hot 90s supermodel, Leo opted for one with movie star ambitions to boot. He was seen that same year getting cozy with Natasha Henstridge, the rising star who had just won the leading role in the movie Species

8. Bridget Hall 

Leo's name was first linked with this young model when the pair were spotted "canoodling" back in 1998. 

Movie stars. If there's one thing those kooky kids love it's canoodling, right?

Apparently, things didn't go any further than one simple night of love. Ah, well. A night with Leo surely must be better than nothing at all, yes? 

9. Bijou Philips 

In the late 1990s, Bijou Philips, daughter of The Mamas & the Papas singer John Philips, enjoyed a serious "It girl" moment in Hollywood. 

That, of course, involved a brief moment in 1998 dating Leonardo DiCaprio. They didn't last long, as Bijou had her eye on someone else — Elijah Wood, to be specific! 

10. Amber Valletta 

After spotting supermodel/actress Amber in a fashion magazine, Leo sent his agents out on the case to hunt her down! 

Luckily this turned out to be romantic (as opposed to creepier than all get out), and the pair ended up dating for most of 1998.

11. Eva Herzigova

Whilst on the rebound from Valletta in 1998, it's rumored that DiCaprio went after yet another stunning model, Eva Herzigova. Their affair is said to have lasted for only about a month, but the story has never been confirmed — probably because it was so scandalous! You see, Eva Herzigova was married... to Tico Torres, the drummer from Bon Jovi.

RELATED: The Famous Model Who Rejected Leonardo DiCaprio

12. Gisele Bündchen 

Leo's five-year stint with the Brazilian stunner was his first serious (or at least serious enough to go public) long-term romantic relationship. He was so enthralled with Bündchen, whom he dated from 2000 to 2005, that many people speculated that the two of them would wed, but their relationship eventually went sour. 

Gisele famously went on to marry New England Patriots' quarterback Tom Brady. I hear he's quite good at "sports." 

13. Bar Refaeli 

After the split with Gisele, Leo began seeing yet another supermodel, Israeli Bar Refaeli. While the led him to began receiving criticism as a "modelizer" — AKA, a man who only dates models — the truth is that he and Bar shared many common interests, including, perhaps most importantly for Leo, a shared love of environmental activism. 

The two dated on and off from 2005 to 2011. 

14. Blake Lively 

This was one zany, blink-and-you-missed-it type of courtship. For five months following his breakup with Bar in 2011, Leo and Blake were totally inseparable. She even cooked for him! However, whatever Blake may have hoped, the relationship was never meant to be serious.

Silver lining: she went on to marry MAJOR heartthrob Ryan Reynolds. 

15. Erin Heatherton

Leo's next confirmed relationship was with model (you're shocked, I know) Erin Heatherton. Their brief relationship lasted nearly all of 2012, but the two then split due to their separate busy schedules.

(I once tried to dump a man because of my own very busy schedule and he legit had none of it. True story!) 

16. Miranda Kerr

Unconfirmed rumor has it that Victoria's Secret 'Angel' Kerr and DiCaprio have spent time together on and off, at least once in 2012 when she was still involved with Orlando Bloom, and on another three occasions minimum after she and her baby daddy split in October of 2013. 

17. Toni Garrn

Leo dipped his toes back into the Victoria's Secret model pool and started dating "Angel" Toni Garrn in May of 2013. It was smooth sailing for the pair for about a year, until tabloids reports began surfacing that was out Leo partying while surrounded by loads of handsy women, leading Toni to end things in 2014. 

Seriously though, can you even imagine such problems? You're a Victoria's Secret "Angel" and your dude still isn't satisfied. It's nuts!

18. Kelly Rohrbach

When Leo met Kelly, a professional golfer and brain surgeon — just kidding, she's also a model — in 2015, everyone thought that Leo had finally met his match. They were photographed together everywhere and rumors of an engagement began to circulate. 

Alas, they promptly stopped circulating when the pair split in 2016. 

19. Rihanna 

When Leo and Rihanna were spotted together at a club in Paris (THE LIVES THESE PEOPLE LEAD) being all flirtatious the internet went nuts. 

Were Leo and Rihanna dating? They said no, but our hearts (and our hearts' vaginas) refused to believe it. Whether or not the pair ever did have a fling or if have always remained "just friends" (with benefits — my theory), is something only the two of them can say for sure!

20. Lauren Hutton

DiCaprio brought mom Irmelin Indenbirken along as his date to the 2016 Academy Awards, which worked out perfectly as he finally brought home his first Oscar for Best Actor in The Revenant. Partying with your mom on such a stellar, however, would just be weird.

Word on the street is that Lauren Hutton, star of UK hit series 'Made in Chelsea' (and who is said to have first met Leo in the Caribbean back in 2014), met up with him after his big Oscar win for a what was surely a night to be remembered.

21. Kate Winslet

Leo and Kate have been the best of friends ever since they starred together in the blockbuster flick, Titantic. So when they were recently spotted on a cruise together being extra cozy, everyone (my inner teenager included) lost their minds thinking that the two single actors might finally be connecting romantically.

Unfortunately, the too-good-to-be-true couple quickly shut down the rumors, reminding folks that they've been friends for years... which is exactly what you WOULD say if you were two high-profile actors eager to keep your budding romance with one another on the down-low, yes?

I mean, Kate even admitted that she and Leo quote lines from Titanic to each other!

Exactly.

Or, at least, a girl can dream...

Rebecca Jane Stokes is a sex, humor and lifestyle writer living in Brooklyn, New York with her cat, Batman. She hosts the sex, love, and dating advice show, Becca After Dark on YourTango's Facebook Page every Tuesday and Thursday at 10:15 pm Eastern. For more of her work, check out her Tumblr.