Women Dated: Juliette Lewis (1993), Brittany Daniel (1994-95), Bridget Hall (1995), Claire Danes (1995-96), Kristen Zang (1996-1997), Helena Christensen (1997), Linnea Dietrichson (1997), Eva Herzigova (1998), Vanessa Hayden (1998), Kidada Jones (1998), Bijou Phillips (1998), Amber Valletta (1998), Demi Moore (1998, 2002), Gisele Bundchen (2000-2005), Sienna Miller (2005), Bar Refaeli (2006-2009, 2010-2011), Emma Miller (2009), Ashley Roberts (2009), Anne Vyalitsyna (2009), Blake Lively (2011), Alyce Crawford (2011), Kendal Schuler (2011), Madalina Ghenea (2011), Erin Heatherton (2011-present)
Words fail. In terms of quality, Leo is unmatched. This is the age of serial monogamy, remember—a guy is just not going to put up Warren Beatty numbers. Some of these ladies carbon-date to the "Pussy Posse" era, when DiCaprio led a group of young bird-doggers that included Tobey McGuire, Kevin Connolly, Lukas Haas, and magician David Blaine, company that insured Leo was always the best looking guy in the room.
When it comes to your own pursuit of the pretty girls, don't waste your time praying to God or bargaining with the Devil. Just ask yourself WWLD—What Would Leo Do?
Note: No, we don't know what Leo would do. And if we did, we sure as hell wouldn't post it on the Internet for free. It's more of a rhetorical question.