A definitive list of Leonardo DiCaprio’s (alleged) conquests

Pull up a chair, there are many...

Gisele Bundchen Kelly Rohrbach Bar Refaeli Blake Lively Leonardo DiCaprio
Leo has a type Four of DiCaprio's many (alleged) conquests. Image Picture Instagram

Now that Leonardo DiCaprio finally has an Oscar, he’s able to turn his attention to his other big pursuit in life: women.

The 41-year-old isn’t just a great actor, he’s a bona fide international playboy. The list of DiCaprio’s (alleged) girlfriends is long and makes certain things abundantly clear: Leo likes leggy blonde models (preferably Victoria’s Secret) between the ages of 20 and 25.

Here’s a rundown of the many women in DiCaprio’s life. And remember, these are only the ones we know of…


1

Bridget Hall

Starting how he intended to go on, DiCaprio reportedly had a one-time fling with a Victoria’s Secret model while he was still a teen.

2

Bobbie Brown

No not that one. Brown starred in the music video for Warrant’s Cherry Pie and was a former Miss USA. DiCaprio apparently seduced her by singing TLC’s Waterfalls. (Apparently.)

3

Brittany Daniel

Leo was rumoured to have had a moment with his Basketball Diaries co-star after they got intimate on-screen.

4

Kristen Zang

His first (known) long-term girlfriend, DiCaprio dated model Kristen for more than a year in the mid-90s.

5

Naomi Campbell

My collector's editions @taschenbooks is almost out! 📸: @stevenmeisel_ #throwbackthursdays (link in bio)

A photo posted by Naomi Campbell (@iamnaomicampbell) on

Purely a rumour, but this apparently pair made an unbelievably attractive pair for a brief moment nearly 20 years ago. They’re still apparently good pals to this day.

6

Helena Christensen

After the success of Titanic DiCaprio shot into the stratosphere. He celebrated by romancing bombshell Helena Christensen.

7

Natasha Henstridge

Henstridge was a model and star of Species when she had a thing with DiCaprio. Later she married Darius Danesh of Pop Idol fame.

8

Amber Valletta

Thank you @luigiandiango for the gorgeous day and photos! @luimagazine 📸❤️

A photo posted by ambervalletta (@ambervalletta) on

DiCaprio reportedly took a shine to Amber after spotting her in a magazine. He had his “people” put in some calls and arranged a rendezvous.

9

Bijou Phillips

This short-lived relationship helped Phillips get her start in acting. He introduced her to Hollywood bigwigs and we’ve since seen her in films ranging from Almost Famous to Choke.

10

Eva Herzigova

This one’s a little scandalous. DiCaprio and Herzigova are said to have had an affair while the Victoria’s Secret model was still married to Tico Torres.

11

Anne Vyalitsyna

DiCaprio and Victoria’s Secret runway star Anne met in 2009 in Ibiza. You know what happened next.

12

Kidada Jones

Hollywood royalty, Kidada is the daughter of Quincy Jones and sister of actress and screenwriter Rashida Jones.

13

Gisele Bündchen

Gisele was fast becoming a catwalk star when she started dating DiCaprio in 2000. They were and off for around five years before calling it quits. Gisele is now married to America Football star Tom Brady.

14

Bar Refaeli

The one that go away? Israeli model Bar was DiCaprio’s other half for six years from 2005 to 2011. The Victoria’s Secret star is now married to businessman Adi Ezra.

15

Blake Lively

Let It Glo

A photo posted by Blake Lively (@blakelively) on

One magical summer Leo and Blake were spotted canoodling on a yacht in France. After five months, the pair fizzled out and Lively is now married to Ryan Reynolds.

16

Alyce Crawford

DiCaprio doesn’t hang around. He reportedly hooked up with Australia’s Next Top Model contestant Crawford days after splitting from Blake Lively.

17

Mădălina Ghenea

The Romanian-born model was spotted with DiCaprio on multiple occasions while he was in Australia filming The Great Gatsby. Jay Gatsby himself has nothing on Leo’s prolific playboy lifestyle. 

18

Erin Heatherton

See you soon London! Going to be so fun 😘

A photo posted by Erin Heatherton (@erinheathertonlegit) on

Erin is blonde, leggy and a lingerie model for Victoria’s Secret. Right in DiCaprio’s wheelhouse. The pair lasted for a year before going their separate ways.

19

Margarita Gauchet

Leo spotted Margarita on the set of The Wolf Of Wall Street and used buddy Jonah Hill to get her number – that’s what friends are for. 

20

Toni Garrn

DiCaprio took model Garrn to the Golden Globes after-party a couple of years back while he was on the awards trail for The Wolf Of Wall Street.

21

Kelly Rohrbach

sup brah 🏄🏼 @calzedonia summer campaign coming soon…

A photo posted by @kellyrohrbach on

Victoria Secret’s star Rohrbach dated DiCaprio in 2015 but the pair didn’t go the distance. Now she’s switched to acting and will fill Pamela Anderson’s sizeable swimsuit in the Baywatch movie.

22

Laura Whitmore

Allegedly DiCaprio and TV presenter Whitmore got up close and personal after the BAFTAs earlier this year. Allegedly.

23

Victoria Robinson

🦁

A photo posted by Victoria Robinson (@victorialeerobinson) on

Breaking with Victoria’s Secret tradition, DiCaprio is said to have had dated Ford model Victoria this year. The duo were spotted leaving a Justin Bieber after party together. That’s showbiz for you.

24

Rihanna

Were they? Weren’t they? Are they just friends? Nobody knows for sure but where there’s smoke around DiCaprio, fire normally follows…

25

Roxy Horner

DiCaprio’s latest love is a 24-year-old British model who once dated TOWIE star Joey Essex.

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Loaded digital media manager Simon Reynolds has written about film and entertainment for various leading websites since 2008. Follow Simon at @simonreyn

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