18 Most Stunning Women Leonardo DiCaprio Has Ever Dated

We have all had a crush on Leonardo DiCaprio at some point in our lives – yes, men too. From the moment he hit the big screen in Titanic, we knew he was going to be one to watch. All these years later, and DiCaprio is still not hitched. Instead, the Hollywood heavyweight has had quite the vast love life; a model-filled love life, to be precise. When it comes to the Once Upon a Time In Hollywood star, the hardest thing to do is keep up with his relationships.

His dating history? To keep it short and sweet, it is a list of numerous Victoria’s Secret Angels. Although the actor is in his 40s, the heartthrob can snatch up a bunch of models that are half his age. DiCaprio is a hit with the ladies, and let us remind you, they’ve all been super hot chicks. Take a look, and do not envy him.

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18 Sports Illustrated Model Kelly Rohrbach Was His

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She looks like a smoking hot goddess, doesn’t she? The blonde model (yes, again) who graced the page of Sports Illustrated Swimsuit Issue, was one of DiCaprio’s latest leading ladies.

Her smile has us swooning, along with her girl-next-door look, but it wasn’t enough for the actor. And she has the brains, too.

17 He Should’ve Never Let Madalina Ghenea Go

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A brunette? Wait, did DiCaprio knock his head? The Romanian model, that looked different from his past girlfriends, was linked with the actor in 2012. We cannot even look at this photo of Ghenea without drooling.

We are a fan of hers and are digging the legs in nylons – is the Titanic actor blind or what?

16 The Angel, Bar Refaeli

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How many Victoria’s Secret romances has DiCaprio had?

This VS Angel is the sixth on his list, and he was completely gaga over her. Besides her good looks, she’s an advocate for the environment and promotes peace; the whole package. How he could’ve let go of this feisty and fierce lady in an animal print swimsuit is beyond our comprehension.

15 The Time He Was With Toni Garrn

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Surprise! Another German, tall and slender blonde model that was wrapped around the actor’s arms. We’re really scratching our heads over the fact that he’d give up on her while looking at her stunning figure in a white gown.

Classy and sophisticated, we thought she tied the actor down, but they called it quits.

14 Leo Went For The Russian, Anne Vyalitsyna

With those dashing looks, Anne V must be worth a trillion bucks! The most natural of all, Victoria’s Secret model is a keeper. However, DiCaprio did not break his “break-up” spell and called it off with her, too.

He couldn’t keep his hands off her back then, and neither would we.

13 Victoria Robinson, Who We Can’t Keep Our Eyes Off Of

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Robinson is truly one-of-a-kind! Channeling her inner Sophia Loren, we are not the least surprised that DiCaprio fell in love with her. With ocean blue eyes and thick dark locks, we must admit that the A-lister is a man of good taste.

The model was 23 when the pair were romantically linked, and now, we’re hoping she’s a single lady.

12 Leo’s Newest It-Girl

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Leo’s current girlfriend is an exotic brunette – maybe she’s finally the one! If a woman looks that sultry in a blazer and pants, we cannot imagine how she looks when she struts in a bikini. She’s a model, too (what a surprise), and the two are pretty steady.

Plus, her stepfather is Al Pacino, so we would not mess with that if we were him. She may only be 22, but she’s fine, so who cares?

11 His Model Addiction Started With Kristen Zang

If you’re an avid fan of DiCaprio from his early days, then you may just agree with us that Zang was, “the one that got away.”

Not only was she stunning in every sense of the word when the two were dating, but she would look at him as if he was her entire world. We think DiCaprio became obsessed with models because of her.

10 His First Girlfriend Was Brittany Daniel

You probably remember actress, Brittany Daniel, in White Chicks, because you fell in love with her alluring looks. Well, she once upon a time was one of DiCaprio’s main girls.

They starred in a film together, The Basketball Diaries, at the start of his career; he clearly could not resist her as they started dating IRL quickly after. Now she is a toned hot tamale that he let go.

9 Leo Hunted Amber Valletta

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This luscious beauty did not have to do much to get DiCaprio. The supermodel, with a hypnotizing regard, was in the pages of a magazine when the actor first saw her. Because of her piercing beauty, DiCaprio sought her out by asking people to arrange a meeting between the two.

Crazily enough, things didn’t work out with the high-profile babe.

8 Before Tom Brady Came Along, There Was Leo

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We have a feeling that most of you forgot that DiCaprio dated the football GOAT’s wife first. Most people envy Brady because of his steamy wife but forget that DiCaprio dated Bundchen for five years before.

It took the beautiful model (that all men love), to call it quits with the actor, as he did not put a ring on it.

7 Leo And His Bijou

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Bijou Phillips was a real “bijoux,” but DiCaprio clearly did not appreciate her beauty. DiCaprio dated the model-turned-actress for a while, and she was only a teen then. Although he boosted her acting career, her looks did a lot for her, too.

Her elegance is timeless, and she doesn’t need to be in a bikini to look steamy. She would’ve been a hot mama!

6 Back Then, Leo Snatched Naomi Campbell

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Which guy in the 90s didn’t have a poster of Naomi Campbell on their wall? While she may have been in your rooms, she was holding hands with the silver screen actor. Don’t kid yourself, she was also a Victoria’s Secret Angel, of course.

Plus, you all know how hot this famous model is – no explanation is needed.

5 Claire Danes Was His Juliet

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Yes, at just 17-years-old, Danes became DiCaprio’s real-life Juliet. We live in a world that does not know Romeo and Juliet, but when Danes first met DiCaprio and stared at him dead in the eyes, he became her Romeo.

He constantly gushed over her, and he probably would now, too. The spark didn’t last, but her beauty did, as she aged like fine wine.

4 After Titanic, Came Helena Christensen

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This butterfly could land on our lap any day! She was sizzling then, and she’s even more gorgeous now.

The runway model is famously known for baring her chest while prancing up and down way back when, and we’re guessing that is what may have caught his eye. Either way, he didn’t deserve this leggy and gorgeous woman.

3 Emma Miller Was Brief

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Our eyes are currently glued to the screen, and we assume we do not need to explain why. Seriously, who else can pull off a cut-out dress and make it look classy?

His encounter with Miller was brief, as it occurred right after his split from Refaeli. She must have really swept him off his feet with her charm – no kidding.

2 Alyce Crawford Was One Of Our Faves

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Ouch – we just got bit by the lovebug! Crawford looks like the ultimate bronzed goddess in this photo; just look at her shimmery long legs. We may have put her on the bottom of the list because we keep the best for last.

The Australian swimwear model would make us visit Down Under in a heartbeat, so we are not surprised DiCaprio did the same.

1 He Dated A Gossip Girl

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Although we are so thrilled that Blake Lively is now married to Ryan Reynolds, we got seriously excited when we first spotted the Gossip Girl actress with DiCaprio.

DiCaprio was smitten by the blue-eyed beauty, and we went bonkers over how hot they looked together. We were rooting for them, but a couple of months in, and DiCaprio cut the ties.

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