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Here’s The Complete List Of Women Leonardo DiCaprio Has Allegedly Dated

By / 06.18.14
The 77th Annual Academy Awards - Arrivals

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Leonardo DiCaprio is either a very sad, broken man, or he’s having more fun than any of us. Sometimes it’s hard to tell. One moment, he’s gleefully telling Justin Bieber to screw off; the next, he’s reportedly flying in dozens of women to party with him on his yacht in Brazil, something his “wife” did not take well. There’s something kind of tragic about that…but it also sounds great. I take back what I said: Leo’s living life right. (Maybe?)

Since the early 1990s, DiCaprio has been rumored to have dated practically every gorgeous woman in Hollywood and the modeling world. Some of these reports are more confirmed than others (no, he never slept with Kate Winslet, despite what TitanicTits.com says). Here are nearly two dozen ladies who we’re, with some help from Zimbio, pretty sure he was involved with.

1. Bridget Hall (1994)

Bridget Hall;Leonardo Dicaprio

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2. Brittany Daniel (1995)

Ron Galella Archive - File Photos

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3. Naomi Campbell (1995)

Naomi Campbell

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4. Kristen Zang (1996)

"Romeo + Juliet" Hollywood Premiere

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5. Helena Christensen (1997)

Fashion Show: Ready To Wear, Spring -Summer 1998 In Paris, France On October 14, 1997.

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6. Bijou Phillips (1998)

Bijou Phillips

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7. Amber Valletta (1998)

Amber Valletta attending Council of Fashion Designers of Ame

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8. Eva Herzigova (1998)

Eva Herzigova at GQ Men of the Year award ceremony at the Be

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9. Demi Moore (1998)

Demi Moore

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