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The Ladies of Leo: Who Leonardo DiCaprio has Dated!

Leo has had his share of models/actresses over the years, see the ones that we actually know of here!

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    Leonardo Dicaprio, the Ultimate Hollywood Bachelor has been tied to many actresses and models over the years. The following are just the ones we know about!
    Photo: Getty Images
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    1994: Model Bridget Hall
    Photo: Getty Images
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    1995: Naomi Campbell
    Photo: Getty Images
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    "Sweet Valley High" actress Brittany Daniel . . . who was in Leo's 1995 movie "The Basketball Diaries".
    Photo: Getty Images
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    1996: Model Kristen Zang
    Photo: Getty Images
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    1997: Model Helena Christensen
    Photo: Getty Images
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    1998: Demi Moore
    Photo: Getty Images
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    1998: Bijou Phillips
    Photo: Getty Images
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    1998: Model Amber Valletta
    Photo: Getty Images
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    1998: Model Eva Herzigova
    Photo: Getty Images
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    2000: Gisele Bundchen. This is the beginning of a dry spell for Leo. Between 2000 and 2009, Leo only shared himself with TWO women: Gisele and Bar. Assuming he was being faithful.
    Photo: Getty Images
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    2005: Bar Refaeli
    Photo: Getty Images
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    2009: Model Emma Miller
    Photo: Getty Images
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    2009: Model Anne Vyalitsyna
    Photo: Getty Images
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    2009: Ashley Roberts of The Pussycat Dolls
    Photo: Getty Images
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    2011: Blake Lively
    Photo: Getty Images
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    2011: Alyce Crawford
    Photo: Getty Images
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    2011: Model Madalina Ghenea
    Photo: Getty Images
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    2011: Model Kendal Schuler
    Photo: Getty Images
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    2011: Model Erin Heatherton
    Photo: Getty Images
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    2013: Model Toni Garn
    Photo: Getty Images
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    2014: Model Katie Cleary. Leo's latest, although there is no indication that the two are still together.
    Photo: Getty Images