Leonardo DiCaprio is famous for being an exceptionally talented actor and humanitarian, but he's meme'd for taking a really long time to win his first Academy Award and dating a revolving door of Victoria's Secret models. Before Taylor Swift called out Leo's celebrated Saint-Tropez dalliances as evidence of cultural double standards in "The Man," Tina Fey and Amy Poheler joked about Leo's dating habits while hosting the 2014 Golden Globes. The modelizer's not-so-personal life is an enduring topic of conversation, but looking back at Leo's 20 rumored exes, we found more than a parade of societally stereotyped blonde models. These women are humanitarians, activists, and public figures at the top of their fields — call Leo what you want, but the man has taste.
Bridget Hall was the beginning of this famed Leonardo DiCaprio dating history in 1994, three years before he would achieve massive fame with Titanic. True to form, Bridget was a model whose relationship with Leo was never officially confirmed. The pair had been seen canoodling through New York City, also a classic Leo move, but The London Sun reported that Leo dumped Bridget after she found their hookup disappointing. Bridget claims nothing happened between her and the future Oscar nominee winner, and she's been doing just fine in her post-Leo world. Bridget has appeared on the covers of Vogue, Haper's Bazaar, ELLE, and Allure and has been featured in three Sports Illustrated swimsuit issues.
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Supermodel Naomi Campbell's rumored dalliance with Leo didn't last long, but their friendship is one for the ages. The pair has been seen soaking up the sun while yachting in Miami (as spotted by E! News), photobombing 50 Cent, and saving Russian tigers together over the past two decades, proving that it is possible to remain close with your exes. Obviously, you know what Naomi's been up to post-Leo. She's one of the most successful supermodels in the world, has released 25 perfumes through her eponymous brand, and most recently appeared as Rose Spencer-Crane on Fox's Star.
The first confirmed relationship for the notorious modelizer, our Leonardo DiCaprio dating history continues with Kristen Zang, who Leo dated for two years from 1996 to 1998. The New York Daily News reported at the time of their split that Kristen was the love of Leo's life and dumped him because of his immature friends, who a source called "young model-hounds." Kristen is rumored to have dated Nicholas Cage before her relationship with Leo, who apparently dumped her over the phone to elope with Patricia Arquette. Kristen has been happily married since 2014 and dabbled in a few feature film roles in addition to her acting career.
Leo's second Victoria's Secret model (of 10!) was Helena Christensen, who People caught "partying" with Leo at the height of his post-Titanic dreamboat phase. This club-hobbing flirtationship was probably just a fling, but the press was beginning to see a pattern in Leo's not-so-private life. In addition to getting her wings as one of the original Victoria's Secret Angels, Helena served as the founding creative director for Nylon, is an accomplished fashion photographer, and was cited as one of the Magnificent Seven supermodels of the late-'90s.
Natasha Henstridge appeared on the cover of French Cosmopolitan when she was just 15, but the established model is better known today as a Gemini Award-winning sci-fi actress. Natasha was amongst Leo's clubbing friends in the late-'90s with a reported fling soon to follow, and her big break as the lead in the box office hit Species aligned perfectly with Leo's astronomical rise to fame. Natasha was an NBC leading lady in the early '00s series She Spies and had a leading role in the CW's criminally underrated The Secret Circle, but Natasha most recently made headlines during the #MeToo movement when she accused director Brett Ratner of sexual assault.
WENN/ Axelle Woussen
Rounding out the trio of women cited by People as Leo's party-hopping model entourage, Amber Valletta supposedly dated the teen dream in 1998. Leonardo DiCaprio dating history lore says that Leo saw Amber in a magazine and had his team track her down. As a bonafide supermodel, Leo could've seen the instantly recognizable star on one of her 13 American Vogue covers in the '90s, and he probably still sees her around on international magazine covers for Harper's Bazaar, Elle, Marie Claire, and i-D (amongst many, many others). Amber is also an actress, music video star, and the spokesperson for Oceana's Seafood Contamination Campaign.
Bijou Phillips was one of the youngest models to ever appear on the cover of Italian Vogue when she was only 13, but the socialite and daughter of The Mamas & the Papas musician John Phillips famously got her start in the acting biz, as reported by The Guardian, when Bijou's then-BF Leo connected her with director James Toback, who cast her in his movie Black and White. After things ended with Leo, Bijou moved on with co-star Elijah Wood, then Sean Lennon, before ending up with Danny Masterson and converting to Scientology.
After Eva Herzigova became the original Wonderbra model, the future actress allegedly took a month-long break from her marriage to Bon Jovi drummer Tico Torres to enjoy a passionate affair with Leo in Europe. Eva has since denied their romantic encounter, but Famous Fix
found a newspaper quote where she admitted to seeing Leo for a month in Naples before their pseudo-relationship collapsed for unknown reasons. Unsurprisingly, Eva's marriage with Tico didn't last either, although she now has three sons with her Italian businessman fiancé Gregorio Marsiaj.
Kristen Zang might have been the love of Leo's life back in the '90s, but his romance with Gisele Bündchen in the early '00s is one of the A-lister's longest relationships. Gisele is happily married to Super Bowl-winning quarterback Tom Brady, but before she met her future husband on a blind date in 2007, she was an integral part of Leonardo DiCaprio dating history from 2000 until 2005. Entertainment Tonight remembers when engagement rumors for Leo and Gisele were the norm during the height of her fame as a Victoria's Secret Angel, back in the days Claudia Schiffer called Gisele the last remaining supermodel.
Leo followed one five-year relationship with another, dating Victoria's Secret model Bar Refaeli from 2005 to 2011 (with one six-month breakup in between). The pair met at a U2 concert in Las Vegas, and Leo was even spotted in Tel Aviv celebrating his 36th birthday with Bar and his mother, Irmelin. People shared rumors that Leo and Bar were planning to wed in fall 2010, but instead, the couple broke up for good in spring 2011. Bar married Israeli businessman Adi Ezra four years later and she remains one of the highest-paid models in Israel in addition to her work as an actress and businesswoman.
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Occasionally single but never unattached, Leo casually dated yet another Victoria's Secret model in 2009 during his break with Bar Refaeli. Russian model Anne Vyalitsyna, known professionally as Anne V, joined Leo on vacation in Ibiza after meeting the newly-single actor in London during filming for Inception. Ace Showbiz linked Leo to The Pussycat Dolls' Ashley Roberts shortly before he met Anne, but the Sports Illustrated swimsuit issue model won Leo's heart in the end, albeit briefly. Anne is best known for appearing in ten consecutive Sports Illustrated swimsuit issues from 2005 to 2014 and for her highly-publicized relationship with Maroon 5 frontman Adam Levine, who's honestly also a bit of a modelizer.
Adriana M. Barraza / WENN
The Daily Mail lurked on Blake Lively's meet-cute with Leo abroad Steven Spielberg's yacht during the 2011 Cannes film festival, and the couple's five-month relationship took them from Monte Carlo to Disneyland, Venice, Los Angeles, New York City, Monaco, Portofino, Australia and Saint-Paul de Vence in France. You know a relationship is one for the history books when it spans more cities than it does months. Blake and Leo met during her audition for The Great Gatsby a few months after Blake's split from longtime boyfriend and co-star Penn Badgley.
If we learned anything from this Leonardo DiCaprio dating history, Leo doesn't stay single for long. While shooting The Great Gatsby in Australia, Leo was spotted out with Romanian model Madalina Ghenea, sparking rumors of a romance reported by Daily Mail Australia. Madalina and Leo were together for a good time, not a long time, and chatter about their fling disappeared as quickly as it began. Since 2011, Madalina has appeared in a handful of films, television series, and music videos. She's also the face of luxury brand Vanitas and has over 770 thousand followers on Instagram.
Following his fling with Blake, Leo ~officially~ went back to Victoria's Secret Angels, dating Erin Heatherton for ten months in 2012. Three years after the pair split due to their crazy schedules, Erin told Daily Mail Australia that she has no bad blood for the Wolf of Wall Street actor, saying, "he's a wonderful person and he's a friend of mine, I wish him all the best." Erin made headlines in May 2019 when she filed for bankruptcy, citing nearly half a million dollars of debt against only six thousand in assets.
After breaking up with Erin Heatherton in October 2012, Leo was single for about six months before starting up with Victoria's Secret model Toni Garrn in May 2013. Tabloids like US Weekly reported that Toni and Leo split in December 2014 after Leo was seen leaving a Miami nightclub with 20 women, a dark era of Leonardo DiCaprio dating history. Since then, Erin has graced the cover of multiple international magazines including 10 countries' editions of Vogue, launched an acting career, and established the Torni Garrn Foundation advocating for the advancement of girls' rights.
Kelly Rohrbach is probably best characterized, in regards to her relationship with Leo, as the Citi Bike Girl. Her relationship with the movie star went viral when they were papped smooching on a Citi Bike ride through New York by People, a fitting date for the environmental activist and his new girlfriend. Kelly was 16 years younger than Leo, but their decision to split in January 2016 after a few months of dating had more to do with their intense work schedules than their age difference. Kelly *is* a model, named the Sports Illustrated Swimsuit Issue's 2015 Rookie of the Year, but first and foremost, she's an actress. You've probably seen her reprising Pamela Anderson's role of C.J. Parker in 2017's Baywatch film alongside Zac Efron.
Rihanna and Leo have denied dating rumors, with Rihanna quoted in The Daily Mail saying she didn't have enough time to date in March 2015, but the pair's influx of public outings (and subsequent disappearance) were fairly convincing evidence of a power couple in the making. Supposedly, Us Weekly sources saw RiRi and Leo kissing and dancing at the 27th birthday part Leonardo hosted for the "Kiss It Better" singer. Honestly, Leo throwing Rihanna a birthday party at all is enough for us to wonder if the Fenty Beauty mogul was just trying to keep her private life private.
Cosmopolitan UK picked up on reports that Leo plucked Laura Whitmore from a group of women at the 2016 BAFTA Awards and flirted with her for the rest of the evening, partying with Leo and a group of female friends until 5 AM. It wasn't the beginning of a fairytale romance in this Leonardo DiCaprio dating history, but being singled out by America's most beloved bachelor is definitely right out of a romantic comedy. Laura is best known in the UK for her stints hosting shows like I'm a Celebrity... Get Me Out of Here! NOW! and being the face of MTV Europe.
Leonardo may be aging, but his girlfriends aren't — and we're not talking about good skincare routines. Leo dated Danish model Nina Agdal, who's 17 years his junior, from July 2016 until May 2017. The pair was spotted beaching it up in Malibu, partying on a boat in Ibiza, and vacationing together in New York, Montauk, and the Bahamas before splitting amicably. People reported Leo danced away his heartbreak with model Ella Ross at The Peppermint Club and Avenue LA in Los Angeles, leading us to conclude that Leo dates 22-year-olds because he's 22 at heart.
Leonardo's most recent long-term girlfriend, Camila Morrone, doesn't care about their 22-year age gap and, according to reports by USA Today, she'd prefer onlookers to mind their own business. Leo's girlfriend since April 2018, when they were spotting PDA-ing at Coachella, Camila has been targeted by online trolls since her relationship with Leo went public, which is totally uncool. When Camila isn't vacationing with her beau or fighting off haters, she's modeling for brands like Moschino, gracing the cover of Turkish Vogue, and appearing in films like James Franco's Bukowski and A24's Never Goin' Back.