Leonardo DiCaprio's model dating reputation is no joke

By Kelli Bender
Updated January 14, 2014 08:30 AM
Kevin Mazur/WireImage

All eyes were on Leonardo DiCaprio at Sunday’s Golden Globes. Not only did the actor win for his role in Wolf of Wall Street, but he was also the source of the night’s greatest zinger.

Cohosts Tina Fey and Amy Poehler invited DiCaprio onstage as a presenter with a not-so-subtle jab at the the actor’s personal life.

“And now, like a supermodel’s vagina, let’s all give a warm welcome to Leonardo DiCaprio,” Fey quipped, igniting a wave of laughter.

DiCaprio responded to the remark with a knowing smile before hustling into the nominees for best actress in a drama. Even the actor can’t deny that he’s got a type.

Check out the timeline below of past loves, former flings, and rumored hook-ups that exemplify exactly why DiCaprio earned his rep as Hollywood’s top modelizer.

Bridget Hall (1994)

American model Bridget Hall has the honor of being the first supermodel connected to the actor. The pair were spotted canoodling together, but never confirmed their relationship. Rumors abound that Hall ultimately found the experience “disappointing.”

Naomi Campbell (1995)

Starting off strong, DiCaprio’s second catwalk connection was with supermodel Naomi Campbell. Rumors claim the duo had a brief fling and then decided they would work better as friends. Today, these entertainment superpowers can be spotted platonically yachting.

Kristen Zang (1996-97)

Zang snagged some time with DiCaprio before he transformed into a Titantic megastar. Not quite star-crossed lovers, this couple did attend the premiere of Romeo + Juliet together.

Helena Christensen (1997)


served as DiCaprio’s ticket to all of Hollywood’s glory, including the dating field. The actor allegedly chose Christensen as the first model to take out post-iceberg.

Bijou Phillips (1998)

The actor is credited with dating model-turned-actress Phillips and jumpstarting the starlet’s career, introducing her to Black and White director James Toback.

Amber Valletta (1998)

The actor’s second fling of 1998 was with another model-turned-actress, Amber Valletta. As the story allegedly goes, man spots model in a magazine, man has his people call hers to arrange meet-up, man and model briefly date. Basically, DiCaprio makes dating look easier than flipping through a catalogue.

Eva Herzigova (1998)

Herzigova rounds out 1998’s hat trick. DiCaprio and the model were said to have a one month relationship, but never confirmed the tryst. Perhaps because Herzigova was married to Bon Jovi drummer Tico Torres throughout the alleged affair.

Gisele Bündchen (2000-05)

Mrs. Brady tried romancing the difficult DiCaprio for close to six years, going through several on-again, off-again moments before officially calling it quits in 2005.

Bar Refaeli (2005-09) & (2010-11)

Israeli model Refaeli started out as DiCaprio’s stunning 20-year-old fling, but evolved into a serious relationship. Many DiCaprio trackers thought the pair would settle down, especially after reuniting after a six-month break in 2010. Alas, there were more models ahead.

Anne Vyalitsyna (2009)

Before she was Adam Levine‘s ex, Russian model Vyalitsyna (also known as Anne V. in the industry) was connected to DiCaprio. Some say that she and the actor had a brief romance while DiCaprio was on a break from his relationship with Refaeli.

Madalina Ghenea (2011)

DiCaprio entertaining Romanian model Ghenea during his stay in Australia for The Great Gatsby. Reports said the rumored relationship lasted a few dinners before fizzling out.

Erin Heatherton (2011-12)

DiCaprio’s recent work schedule crippled this relationship. After dating for nearly a year, the couple had a friendly spilt, citing the actor’s demanding movie projects as the main factor.

Toni Garrn (2013-?)

The newest inductee into DiCaprio’s dating history, Toni Garrn is a Victoria’s Secret model the actor started dating in June 2013. Will this catwalker be “the one”?

BONUS: Cara Delevingne (Not Happening)

Not every model has a weak spot for this Romeo. DiCaprio reportedly tried to woo the 21-year-old at a party, but he was rebuffed. Delevingne is said to have found the actor too old and too forward to date. Strike one for Leo!

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