The 23 Hottest Girlfriends of Leonardo DiCaprio

by: Esteban On  Wednesday, August 15, 2012
Tags:  Celebrities   Girlfriends   Hot Girls   Women  

hottest girlfriends of leonardo dicaprio

We all know that male celebrities do really well with the ladies, but some do better than others. Why? It’s hard to say. Extremely good-looking dudes obviously have an advantage, but it’s got to be more than that. It’s got to have something to do with their tactical approach to dating women, combined with a never say die attitude.

Anyway, whatever it is, some guys have it. And one of these guys is Hollywood heartthrob Leonardo DiCaprio. So today I thought I’d make all you refined guys out there jealous by doing a list of Leo’s hottest girlfriends over the last 20 years.

But let’s just start off by stating the obvious: the term “girlfriends” is probably a bit strong. This guy is notoriously averse to commitment, so most of the women on this list are better classified as “special lady friends,” also known as “hook-ups”…which is probably even more impressive.

Also impressive? The fact that there are women Leo was rumored to have “dated” that aren’t even on this list. But enough of that. Let’s get this tour of Leonardo DiCaprio’s legendary love life under way, shall we?

23. Brittany Daniel

23 brittany daniel

Brittany Daniel starred in the film that launched Leo’s career—1995′s Basketball Diaries. Well, she didn’t star, but she was in it, playing the role of the “Blinkie,” a hot chick who seduces Leo’s character. Of course, it turned out that Brittany was a really, really convincing actor, and the two ended up dating for a while in 1994. Leo was 19, Brittany was 18.

Age Difference: Leo +1.5 years

22. Bridget Hall

22 Bridget Hall

Bridget Hall was probably DiCaprio’s first supermodel girlfriend, though certainly not his last. They dated in 1994 and, according to UK “newspaper” The Sun, Leo took Bridget’s virginity, and she was not exactly impressed with his skills in the bedroom. Of course, she denies that report (at least the “not impressed” part), but come on, we all know how reputable The Sun is.

Age Difference: Leo +3 years

21. Naomi Campbell

21 Naomi Campbell

For Leo’s next foray into the world of supermodels, he chose queen bitch of fashion world Naomi Campbell. The two reported had a brief fling sometime in 1995.

Age Difference: Leo -4.5 years

20. Claire Danes

20 Claire Danes

After Leo discovered that Naomi Campbell is an insufferable human being (or so I’ve heard), Mr. DiCaprio dated his Romeo + Juliet co-star Claire Danes for about a year from 1995 to 1996—though they never made it official. But I guess they figured their love scenes went so well it would be crazy to stop cold turkey.

Age Difference: Leo +5 years.

19. Kristen Zang

19 Kristen Zang

LDC is said to have dated model Kristen Zang on and off from 1996 to 1997, a period that overlaps a bit with his supposed relationship with Claire Danes. (Like I said in the intro, DiCaprio isn’t really into the whole commitment thing.) In fact, Zang was his date to the premier of Romeo + Juliet. So these two, at least, were official. Some rumors flew around that Zang broke it off for good when Titanic was about to come out because she knew he was going to be a megastar and she didn’t want to be a part of it. But, um, yeah, that sounds like spin control to me. My guess is he dumped her.

Age Difference: Leo -5 months

18. Linnea Dietrichson

18 Linnea Dietrichson

In 1997, Leo had a little thing with British swimsuit model Linnea Dietrichson. Apparently Linnea said he picked her up in a club and took her back to his place, where he proceeded to stumble all over pass out after only 5 minutes. But hey, a hook up is a hook up.

Age Difference: unknown

17. Helena Christensen

17 Helena Christiensen

Man, 1997 was a good year for this guy. After Titanic shattered box office records, Leo could get with just about any supermodel he wanted. And that included Danish beauty and “pioneering” Victoria’s Secret angel Helena Christensen.

Age Difference: Leo -6 years

16. Bijou Phillips

16 Bijou Phillips

In 1998, Leo kept reaping the rewards of the world’s most epic chick flick (Titanic), scoring a brief relationship with model-turned-actress Bijou Philllips. In fact, she says he’s the one who got her her first movie role in 1999′s Black and White. So that’s nice.

Age Difference: Leo +6 years

15. Amber Valletta

15 Amber Valletta

Leo’s relationship with model Amber Valletta is the stuff of legends. Apparently he saw this gorgeous woman in a magazine, told his people to contact her people to set up a meeting, and…well, you know. So basically Leo is one of the only guys in the world who considers Vogue a girlfriend catalogue.

Age Difference: nil

14. Liv Tyler

14 Liv Tyler

What? Steven Tyler’s daughter? That’s awesome. Apparently in the late 90s, some photos surface of the two getting very cozy with each other as a party.

Age Difference: Leo +3 years

13. Eva Herzigova

13 Eva Herzigova

Rounding out the 1998 vintage of LDC girlfriends is Guess, Victoria’s Secret, and Sports Illustrated Swimsuit model Eva Herzigova. She was married to Bon Jovi drummer Tico Torres at the time, but I guess you just don’t turn down Leonardo DiCaprio.

Age Difference: Leo -1 year

12. Gisele Bundchen

12 Giselle Bundchen

Gisele Bundchen, aka Mrs. Tom Brady, was one of Leo’s longest flings. They were on again/off again from 2000 to 2005, when they finally called it quits for good. Apparently she got tired of his inability to abstain from other ridiculously hot women.

Age Difference: Leo +6 years

11. Trishelle Cannatella

11 Trishelle Cannatella

During one of Leo’s breakups with Gisele, he supposedly hooked up with reality TV “star” (I use that term even more loosely here than I used “girlfriend” in the intro) and Lingerie football league “athlete” Trishelle Cannatella. Because, hey, why not?

Age Difference: Leo +5 years

10. Sienna Miller

10 sienna miller

Word on the street back in 2005 was that Sienna Miller used Leo to get even with her philandering hubby, Jude Law. And it would make sense, too, given that the two are kind of similar-looking.

Age Difference: Leo +7 years

9. Bar Refaeli

9 Bar Refaeli

In 2006 Leo embarked on his second (and only other) long term on again/off again relationship. This time it was with Israeli super-hottie Bar Refaeli, who he met backstage at a U2 concert in Vegas. The two were together, more or less, from 2006 to 2011.

Age Difference: Leo +11 years

8. Ashley Roberts

8 Ashley Roberts

In 2009 LDC and Bar Refaeli had one of their off again periods…and Leo took full advantage of it. First up was Ashley Roberts of the Pussycat Dolls, who he met at a London party.

Age Difference: Leo +7 years

7. Emma Miller

7 Emma Miller

While still on that break from Bar Refaeli, Leo went on at least one date with British fashion model Emma Miller, who was dating Jesse Metcalfe (the guy from Desperate Housewives) at the time…and yes, there were lots of “Jesse’s Girl” jokes in the tabloids at the time.

Age Difference: Leo +15 years

(As you can see, as is the case with most bachelor celebrities, as Leo has gotten older the age difference between himself and his female companions has grown larger.)

6. Anne Vyalitsyna

6 Anne Vyalitsyna

The last of Leo’s 2009 ladies while he and Bar Refaeli took an intermission was Sports Illustrated Swimsuit all-star Anne Vyalitsyna. Now she was a wise choice.

Age Difference: Leo +12 years

5. Blake Lively

5 Blake Lively

After giving it a go again in 2009 and 2010, Leo and Bar Refaeli broke it off for good in 2011. Obviously, it didn’t take Leo very long to get back into the swing of things, as pretty soon he was dating Gossip Girl star Blake Lively. Who is super attractive. The relationship lasted about 5 months.

Age Difference: Leo +13 years

4. Alyce Crawford


While filming the upcoming Great Gatsby in Australia, Leo reportedly became acquainted with not one but two Aussie models. Alyce Crawfor, a former contestant on Australia’s Next Top Model, was one of them.

Age Difference: Leo +16 years

3. Kendal Schuler

3 Kendal Schuler

The other Aussie model who kept LDC company while doing the film adaptation of the Great American Novel down under in Australia? That would be Kendal Schuler. She apparently met Leo a few years ago in L.A., and he looked her up while in Australia filming.

Age Difference: Leo + 17 years

(Okay, now these age discrepancies are getting a little ridiculous.)

2. Madalina Ghenea

2 Madalina Ghenea

Leo didn’t just date Australian models while filming Gatsby. He also dated Romanian-born Italian model Madalina Ghenea for a spell back in October. It’s amazing he found the time to actually shoot the picture, ins’t it?

Age Difference: Leo +14 years

1. Erin Heatherton

1 Erin Heatherton

At long last we arrive at Leonardo DiCaprio’s current girlfriend, Victoria’s Secret Angel Erin Heatherton. Well, at least I think she’s his current girlfriend. The way things seem to go with this guy, that could very well change by the time this is published tomorrow. But for now, yes, Leo is dating this amazingly beautiful woman. Because what can I say? The guy is a babe magnet.

Age Difference: Leo +15 years