It’s no secret that Leonardo DiCaprio, 44, has a reputation as a ladies’ man. He’s been a confirmed bachelor since hitting mega-stardom in the ’90s, meaning countless women lay claim to being in Leo’s little black book. But how has life turned out for some of the Oscar winner’s most public pursuits?
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Leo and supermodel Kate Moss dated back in 1994 when she was 20. The fashion icon is 45 today and recently launched a campaign with Alexander McQueen.
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Bridget Hall was a young model when she was linked to Leo, though she’s denied they were a thing. She is now 41.
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Leo dated Kristen Zang for a little over a year back when she was in her early 20s. She is now 45 and lives in the Northwest with her contractor husband. She also makes dog food with her business Emma Lou’s Kitchen.
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Natasha Henstridge had an apparent fling with Leo in 1997 at the age of 23. She is now 44 and living in Halifax, Nova Scotia.
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Helena Christensen and Leo were linked back in 1997. The model just turned 50 and is still rocking the bustiers of her early modeling days.
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Demi Moore had a rumored romance with Leo in 1997. She is set to release a tell-all memoir called “Inside Out” in September, which may give a deeper look into her relationships.
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They later decided to be just friends, but in the mid ’90s, Leo and Naomi Campbell had a rumored fling. Naomi is still stomping the runway, and just launched her own YouTube channel.
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Model Eva Herzigova briefly dated Leo at the age of 25. She is now 46 and editor-at-large for Vogue Czechoslovakia.
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Leo reportedly reached out to Amber Valetta after seeing her modeling photos in a magazine. After a reported tryst, Valetta is still making headlines in the fashion world, recently turning heads at the Met Gala in a pantsless outfit.
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Actress Bijou Phillips dated Leo in the late ’90s. She now has a daughter and writes for Kourtney Kardashian’s Poosh website.
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Gisele Bündchen was Leo’s longest relationship, clocking in at six years. The two split in 2005, and she went on to marry Patriots quarterback Tom Brady in 2009.
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Kidada Jones was spotted with Leo in 1999 but the tryst didn’t last. The daughter of Quincy Jones and Peggy Lipton has since gone on to write a book called “School of Awake” and works as a fashion designer.
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Bar Refaeli was with Leo on and off from 2005 to 2011. She is now married to businessman Adi Ezra, and they are expecting their third child together.
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A pre-Ryan Reynolds Blake Lively canoodled with DiCaprio, dating him from May to October 2011. She is now expecting her third child with husband Ryan Reynolds.
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DiCaprio had a 10-month relationship with model Erin Heatherton from late 2011 to October 2012. She has since filed for bankruptcy and had numerous complaints from her neighbors about alleged wild parties and noise.
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Miranda Kerr hung out with DiCaprio in November 2013 after her split from husband Orlando Bloom. She is now pregnant with her second child with current husband Evan Spiegel.
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Victoria’s Secret model Toni Garrn dated Leo from 2013 to 2014. She continues to model today and recently posed on the cover of Harper’s Bazaar Singapore.
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After dating Leo in 2015, Kelly Rohrbach landed a role in the “Baywatch” movie. Earlier this summer, she quietly married Walmart heir Steuart Walton.
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Romanian model Madalina Ghenea was spotted on dates with Leo in Sydney, Australia, when he was filming “The Great Gatsby” in October 2011. The two may have rubbed shoulders again recently, as she was at the premiere of his film “Once Upon a Time in Hollywood” in Cannes.
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Nina Agdal and Leo dated from 2016 to 2017, but post-breakup, she has moved on to Christie Brinkley’s son, Jack Brinkley Cook.
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Victoria’s Secret model Lorena Rae was spotted out multiple times with Leo in 2017. She just turned 25 in July. Leo has since moved on to 23-year-old model Camila Morrone, his current girlfriend.
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