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Rihanna
From 2015 to 2015 (Rumored Encounter)
Toni Garrn
From 2013 to 2014 (Relationship)
Alesia Riabenkova
From 2013 to 2013 (Relationship)
Miranda Kerr
From 2012 to 2012 (Rumored Encounter)
Erin Heatherton
From 2011 to 2012 (Relationship)
Blake Lively
From 2011 to 2011 (Rumored Relationship)
Kelly Baugher
From 2007 to 2007 (Rumored Encounter)
Bar Refaeli
From 2005 to 2011 (Relationship)
Gisele Bündchen
From 2000 to 2005 (Relationship)
Paris Hilton
From 2000 to 2000 (Rumored Relationship)
Kidada Jones
From 1999 to 1999 (Relationship)
Amber Valletta
From 1998 to 1998 (Rumored Encounter)
Naomi Campbell
From 1998 to 1998 (Relationship)
Vanessa Trump
From 1998 to 1998 (Rumored Encounter)
Demi Moore
From 1997 to 1997 (Encounter)
Natasha Henstridge
From 1997 to 1997 (Encounter)
Kristen Zang
From 1996 to 1997 (Relationship)
Claire Danes
From 1995 to 1996 (Rumored Relationship)
Bridget Hall
From 1994 to 1994 (Encounter)
Trishelle Cannatella
(Rumored Encounter)
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