• Mon, Jan 13 - 4:35 pm ET

A Comprehensive Guide To Every Model Who’s Let Leonardo DiCaprio Into Her Vagina

Original photo via Getty Images; Awful copy & pasting via me.

Photo: Getty Images

One of my favorite jokes of last night was when Tina Fey called out Leonardo DiCaprio on his habit of dating exclusively supermodels (we made our own, too, because we just couldn’t help it). While introducing him onto the stage to talk about American Hustle, she said:

“And now, like a supermodel’s vagina, let’s all give a warm welcome to Leonardo DiCaprio.”

A+, right? We liked it, primarily because it’s true: Leo has managed to date–or at least been “linked to” (i.e. they probably banged but didn’t date)–quite a few supermodels throughout his 39 years on this Earth. Here they are.

See which supermodels Leonardo DiCaprio has dated over the years!

The Basketball Diaries (1995)

Brittany Daniel

They met on the set of The Basketball Diaries (1995). She did some modeling, but not a huge amount. She is now 37, so they were almost the same age at the time which is sort of an accomplishment for the guy.

Her Age: 18
His Age: 19

See which supermodels Leonardo DiCaprio has dated over the years!

Photo: Getty Images

Bridget Hall

Having appeared on magazine covers like VogueHarper’s BazaarELLE and more, Hall is an ultra-experienced, world-renowned model. Leo reportedly took her around to “canoodle” in New York City, which makes me think of Regina George and Aaron Samuels.

Her Age: 16
His Age: 19

See which supermodels Leonardo DiCaprio has dated over the years!

Photo: Getty Images

Naomi Campbell

These two were rumored to have a fling in 1995, but I’m guessing that instead of the aforementioned piercing eyes competition, they had a bitchface-off.

Side note: I would’ve chosen an older picture of Campbell from a decade and a half ago, but I just had to share this one of her, Zac Posen and Georges Antoni.

Her Age: 25
His Age: 21

See which supermodels Leonardo DiCaprio has dated over the years!

Photo: Getty Images

Kristen Zang

They dated 1996 – 1997 and he took her to the premiere of Romeo + Juliet, which sounds pretty fun considering a few of our favorite people were in it.

Her Age: 22
His Age: 22

See which supermodels Leonardo DiCaprio has dated over the years!

Photo: Getty Images

Natasha Henstridge

Natasha’s been in a few decent films (ex: The Whole Nine Yards) and lots of not-so-decent films (ex: Bounce, every other thing she’s done).

Her Age: 23
His Age: 23

Helena Christianson

Photo: Getty Images

Helena Christensen

This Danish fashion model and former Victoria’s Secret Angel could rock a plum suit like nobody’s business. Supposedly, the pair hooked up around Titanic‘s release in 1997.

Her Age: 28
His Age: 23

Amber Valletta

Photo: Getty Images

Amber Valetta

I wonder if the pair had competitions for whose eyes could be more piercing.

Her Age: 24
His Age: 24

See which supermodels Leonardo DiCaprio has dated over the years!

Photo: Getty Images

Vanessa Haydon

“”Leonardo DiCaprio has fallen hard for a stunning young model — and pals say this time it’s love,” claimed Star. ”The superstar is so smitten with blonde beauty Vanessa Haydon that he’s now a one-woman man.” LOL didn’t you guys see The Wolf Of Wall Street?? (Note to self: Go back in time and sell stories to tabloids that are creepily specific.)

Her Age: 21
His Age: 24

See which supermodels Leonardo DiCaprio has dated over the years!

Photo: Getty Images

Eva Herzigova

The original Wonderbra model!

Her Age: 25
His Age: 24

See which supermodels Leonardo DiCaprio has dated over the years!

Photo: Getty Images

Bijou Phillips

After Titanic became the giant success that it did, he dated ex-model (now actress) Bijou Phillips. Here she is with DiCaprio’s Romeo + Juliet costar Claire Danes (with whom he has also been rumored to have had a relationship) at a Zac Posen after party.

Her Age: 18
His Age: 24

Photo: Getty Images

Photo: Getty Images

Gisele Bundchen

At this point, Leo doesn’t even look happy about dating supermodels. Just irritated.

Her Age: 19 – 25
His Age: 25 – 31

See which supermodels Leonardo DiCaprio has dated over the years!

Photo: Getty Images

Bar Refaeli

Just…boredom.

Her Age: 20 – 25
His Age: 31 – 36

See which supermodels Leonardo DiCaprio has dated over the years!

Photo: Getty Images

Blake Lively

Yes, she acts (sort of?), but she also does a lot of modeling, so I’m counting her. Also, please let’s all imagine Leonardo DiCaprio attempting to act as a fellow high schooler in Gossip Girl. Their age difference was about 13 years, after all.

Her Age: 23
His Age: 36

See which supermodels Leonardo DiCaprio has dated over the years!

Photo: Getty Images

Erin Heatherton

It’s fascinating how these women all work in the same office.

Her Age: 22
His Age: 37

Photo: Margarita Gauchet's Twitter

Photo: Margarita Gauchet’s Twitter

Margarita Gauchet

Apparently, Leo’s buddy Jonah Hill hooked him up with the 20-year-old model, because friendship.

Her Age: 20
His Age: 38

See which supermodels Leonardo DiCaprio has dated over the years!

Photo: Getty Images

Toni Garrn

When you Google this woman’s name, it instantly pops up with the suggestion “Toni Garrn Leonardo DiCaprio.” This, by the way, is the way that most of this list has been. Garrn, 21, and DiCaprio, 39, went to the Golden Globes after parties this year together, so I presume that he’ll find a younger model by the Oscars.

Her Age: 21
His Age: 39

[Dating info via WhosDatedWho and Refined Guy]

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  • Lindsey Conklin

    that’s a lot of (young) models, Leo!

  • adamfox

    Helena Christensen’s costume makes me wonder… sometimes I think fashion shows are episodes of Chopped backstage. “You have 20 minutes to make an outfit out of these four mystery ingredients… time starts NOW!”

  • Trista Casey

    Why are you pointing out the age difference between him and the younger ones? Seven of the women on this list are actually his age or even a little older.

    • Samantha Escobar

      The point is that most of the women he dated are in their early 20s. Yes, he was in his early 20s when he dated some of them, but then he got older and continued dating within the exact same demographic. It’s kind of fascinating, kind of bizarre.

    • Andrea

      Another example of why women fear being single as they get older :/

    • tifygodess24

      If society ( mostly men ) didnt make women feel like they are no longer desirable after the age of 30 women would most likely not have this fear. It’s sad.

  • MorrisMountjoy

    It is so very good guide for the every Models.
    http://greencoffeefatburn-us.tumblr.com/

  • MerlePerle

    That picture of vanessa hayden perfectly shows how I aspired to dress for most of high school! Love it!

  • Rachel

    Brittany Daniel! She and her identical twin sister Cynthia (who was also in “The Basketball Diaries–they played Winky and Blinky or whatever the hell their names were) also played Jessica and Elizabeth Wakefield in the Sweet Valley High series. Nice to see their face again.

  • nicole

    um… so that’s not gisele…

  • Hag

    The oldest woman he has ever dated was 28…when he was 23.

  • sibel aruk

    oha lan oha kaç tane karıyla oldun