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)
2. Brittany Daniel (1995)
3. Naomi Campbell (1995)
4. Kristen Zang (1996)
5. Helena Christensen (1997)
6. Bijou Phillips (1998)
7. Amber Valletta (1998)
8. Eva Herzigova (1998)
9. Demi Moore (1998)
10. Gisele Bundchen (2000)
11. Bar Refaeli (2005)
12. Ashley Roberts (2009)
13. Emma Miller (2009)
14. Anne Vyalitsyna (2009)
15. Alyce Crawford (2011)
16. Madalina Ghenea (2011)
17. Kendal Schuler (2011)
18. Blake Lively (2011)
19. Erin Heatherton (2011)
20. Margarita Gauchet (2013)
21. Toni Garrn (2013)
22. Katie Cleary (2014)