Top 10 Women Leonardo DiCaprio Has Dated
Leonardo DiCaprio has dated a plethora of gorgeous women, and we've used whatever resourced we can to rank their relationships! WatchMojo presents the Top 10 Leonardo DiCaprio Relationships! But who will take the top spot on our list? Gisele Bundchen, Blake Lively, or Bar Rafaeli? Watch to find out!
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Forever a bachelor? Leo’s shown no signs of settling down. Welcome to WatchMojo.com and today we’ll be counting down the Top 10 Women Leonardo DiCaprio Has Dated.
For this list, we’re looking at the relationships, both rumored and confirmed, that Leonardo DiCaprio has had in the past. Note that while we’ve tried to make sure the time frames are correct, they can only be as accurate as the information that’s been made publicly available is.
#10: Kelly Rohrbach
2015 - 2016
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Kelly isn’t the first, or even the last, Sports Illustrated model that Leo’s dated, but the “Baywatch” actress is probably the funniest, as proven by her role in the 2017 big screen adaptation of the TV series. The pair started dating in the summer of 2015 with high profile trips to St. Tropez and the U.S. Open. It was more than a summer fling though, and by the fall rumors were swirling that the two were engaged. It turned out not to be true and they quietly broke up sometime in early 2016.
#9: Nina Agdal
2016 - 2017
After his break-up with Kelly Rohrbach, Leo was spotted with the young Ms. Agdal in late spring / the early summer of 2016. The then 24-year-old swimsuit model, who has done work for Victoria’s Secret and Adore Me among others, was a perfect fit for Leo - who is known to have a penchant for blondes and models. Their courtship began after numerous vacations to glamorous locales together, another pattern you’ll quickly notice while tracing Leo’s romantic history. After a year of fun, they reportedly broke up in May 2017. Oh well, call it another celebrity notch in the bed post… for Nina Agdal that is - as she’d previously dated Adam Levine of Maroon 5.
#8: Toni Garrn
2013 - 2014
Like girlfriends before, German-born Toni is also a model with Victoria’s Secret and Sports Illustrated under her belt. This stunning beauty caught Leo’s eye and they dated from around May 2013 to December 2014. A few months after they split, she rebounded - excuse the pun - with NBA player Chandler Parsons, who she dated until some time in 2016. As of September 2017, the 25-year-old had been spotted with Leo on a recent night out. We a reunion hadn’t been confirmed, she’s certainly one to watch.
#7: Erin Heatherton
2011 - 2012
Sometime after his split from a certain blonde actress we’ll be discussing later, Leo was spotted out with Erin Heatherton, a model with her star on the rise at the time. The two clearly loved to travel together, what with trips to Mexico, Hawaii, and Australia, where he was filming “The Great Gatsby.” Unfortunately, their 10-month union didn’t last, with busy schedules once again being blamed. Years after they broke up, Heatherton would continue to speak very highly of DiCaprio and their time together, all the while acknowledging that she’d never been more comfortable than with next boyfriend Felix Bloxsom.
#6: Bridget Hall
1994
You never forget your first…your first Victoria’s Secret model that is. We can thank Bridget Hall for starting off this trend for Leo. Back in 1994, the pair were rumored to have a fling but Bridget has always claimed they were just friends. While there remains some mystery surrounding the details of their relationship, there’s not much guesswork involved in figuring out why Leo would’ve been interested in this stunning beauty. The model has been out of the public eye for quite some time now, but during her heyday she was known for her Versace campaign, magazine covers, and appearances in Sports Illustrated.
#5: Rihanna
2015 - 2016
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Sometimes the most unlikely couples make the most perfect pairings. Stepping away from his usual Victoria’s Secret model type, Leo wound up dating someone who was equally, if not more, famous than himself. A true merging of the A-list, Rihanna and Leo had been rumored to be hooking up since January 2015 when Leo helped plan her 27th birthday party. The duo has been spotted at clubs together as well as at Coachella in April 2016. Neither party has directly addressed rumors about their relationship and sources say they’re just “good friends”. The truth? We’ll likely never know.
#4: Naomi Campbell
1995
Out of all his rumored flings, it seems like Leo got luckiest with this model - in the sense that he made a good friend. The insanely hot alleged couple were rumored to be hooking up in 1995, but decided they were better off as friends; twenty-something years later that seems to have been for the best. Over the years, we’ve heard stories and gotten photos of them together on vacation with friends, discussing tigers in Russia with Putin, and partying with their friend, 50 Cent. Maybe love wasn’t in the cards for them, but we can’t say we don’t enjoy this friendship.
#3: Blake Lively
2011
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At the height of her “Gossip Girl” fame, Blake and Leo appeared together at the 2011 Cannes Film Festival on a yacht. It was a jet-set summer for the two of them with a trip to Verona, Italy, NYC, and LA. They confirmed their breakup in October 2011, but it seemed like they had a fun run while it lasted. We’re still learning tidbits about their relationship today, with a August 2017 Vanity Fair article about the 10-year anniversary of “Gossip Girl” revealing that Blake used to send Leo pics of a doll in various locations while they were apart. This was before Instagram REALLY took off, so we guess that makes sense?
#2: Gisele Bündchen
2000 - 2005
Before she was Mrs. Tom Brady, Gisele and Leo were two halves of one of Hollywood's most beautiful couples. The pair seemed like the real deal with an on-and-off relationship spanning around 5 years, but for whatever reason they couldn't make it work. Gisele chalks it up to both of them being too young at the time and ultimately not right for each other. Of all of Leo's exes, at least Gisele has the honor of being Leo's only Academy Awards date apart from his mom and Kate Winslet.
Before we unveil our number one pick, here are a few honorable mentions:
Kristen Zang
1996 – 1997
Eva Herzigova
1998
Helena Christensen
1997
#1: Bar Refaeli
2005 - 2011
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Out of all his exes, Bar was the one who, at the time, really seemed like she’d get Leo to settle down. Dating for nearly 6 years, the pair consistently came across as a solid couple who got along outside of the circus of Hollywood life. The actor and the Israel-born swimsuit model did have a six-month break-up in 2009 before getting back together, but at the time, everyone thought the reunion would lead to an engagement. Sadly, one never came! Bar’s since moved on, got married and began a family. Is she the one who got away? You tell us!
