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    • Kate Ng
    • Bridget Hall, 1994. DiCaprio (20 at the time) and US model Bridget Hall (then 17) dated at the start of his Hollywood movie career. However, the pair’s relationship has been described as a “fling” and lasted only a brief period of time.
    • Naomi Campbell, 1995. Naomi Campbell attends the 68th Academy Awards, held at the Dorothy Chandler Pavilion in Los Angeles, California, 25th March 1996. (Getty Images)
    • Kristen Zang, 1995-1999. Kristen Zang dated DiCaprio on-and-off for four years when they were both in their early 20s. She wrote an essay for People magazine last year, in which she called out “ageist” headlines about his split from Camila Morrone.
    • Helena Christensen, 1997. Following his extraordinary success with the 1997 classic Titanic, DiCaprio (early twenties) was spotted partying with Danish model Helena Christensen (29 at the time) on a number of occasions.
    • Gisele Bündchen (2000-2005) Often thought of as Leo’s first official “red carpet girlfriend” (she accompanied him to the Oscars), the Brazilian beauty and now Mrs Tom Brady dated DiCaprio when she was 20 years old and he was 26.
    • Bar Refaeli (2005 or 2006-2011) Another one of DiCaprio’s serious relationships in the early days was with the stunning Israeli model Bar Refaeli. The lovebirds were regularly spotted at basketball games and on the streets of Paris, but were mostly known for having something of an on-off relationship.
    • Anne Vyalitsyna (2009) At 35, DiCaprio dated Russian Sports Illustrated and Victoria’s Secret model Anne Vyalitsyna, who was 23 at the time. The couple dated for six months while he and Refaeli were on a break.
    • Blake Lively (2011) After his previous two long relationships ended, DiCaprio, age 37 in 2011, seemed to not be looking for anything too long-term, as evidenced by his fleeting relationship with Blake Lively.
    • Leonardo DiCaprio Has A Reputation For Dating Younger Women
    • Has Leonardo DiCaprio dated Anyone His Age?
    • Fans Have No Sympathy For Leonardo DiCaprio

    Over the course of his career, DiCaprio has been known for dating beautiful younger women. But the internet finally had a say when the Inceptionstar was recently linked to a 19-year-old, Eden Polani. With DiCaprio being 48 years old, the 29-year age gap would be his biggest yet. It could be because of the backlash received that DiCaprio decided to ...

    As much as DiCaprio does not want to be shamed for dating only significantly younger women, the facts are still there that once a woman he is dating reaches a certain age, they break up. That magic number, according to fans, appears to be 25 years of age. A Reddit fan took it upon themselves to create a line graph to show just how old women were wh...

    There are times when fans of those in the spotlight want to commiserate, especially when it feels like every aspect of their life is being put under a microscope. But with DiCaprio dating the same age of women for over two decades now and not appearing to care to date anyone older, fans simply do not have sympathy for him. "Maybe, if he dislikes it...

    • Journalist
    • Bridget Hall (1994) DiCaprio’s first public fling was with model and Vogue cover girl Bridget Hall in 1994. According to The Sun, he dumped her after Bridget found their “night of love” disappointing.
    • Brittany Daniel (1994) After filming together in The Basketball Diaries, DiCaprio and Daniel dated off-screen in 1994.
    • Naomi Campbell (1995) The actor reportedly had a fling with supermodel Naomi Campbell back in 1995, however they went on to become good friends and even spotted hanging out on a yacht in 2013.
    • Kristen Zang (1996-1997) The model and actress was considered to be “the love of his life” according to The New York Daily News. DiCaprio dated Zang for fifteen months and took her as his date to the Romeo + Juliet premiere.
  2. Aug 7, 2024 · 1. Vittoria Ceretti. Ceretti was first linked to DiCaprio in 2023, and the pair were most recently spotted together in August on holiday together in Sardinia, Italy. The 25-year-old Italian...

  3. Feb 6, 2023 · Leonardo DiCaprio has seemingly never dated a woman aged 27 or older — and, at the age of 48, it seems he doesn’t intend to start now. Last year the actor broke up with his long-term...

  4. Aug 7, 2023 · The Jack Dawson hunk then revealed his preference for younger women to the world from 2011 onwards when he dated a string of young models. For around one year he dated Erin Heatherton who was...