He's accumulated quite the collection of ex-girlfriends, hasn't he?
One of the actor's most recent exes is Victoria's Secret model Erin Heatherton. The two carried on a romance that lasted from December 2011 to October 2012.
In late October of 2011, Leo reportedly briefly dated Romanian lingerie model Madalina Diana Ghenea. The two were spotted on a beach in Australia, where DiCaprio was filming "Gatsby."
DiCaprio dated the "Gossip Girl" actress (and now Mrs. Ryan Reynolds) for five months, but the pair ended their relationship in October of 2011.
Leo and the Israeli model Bar Rafaeli met in 2005 and dated for five years. They took a short six-month break somewhere around 2009, but broke up for good in May 2011.
Bündchen and DiCaprio an on-again off-again relationship that lasted from 2001 to 2005. Some sources claim that during their time together, she once dumped him after getting tired of waiting for him to propose.
Czech supermodel Eva Herzigova met DiCaprio at a movie premiere for 1998's "The Man In The Iron Mask," and engaged in a month-long relationship with the actor — all while she was married to Bon Jovi drummer Tico Torres.
Actress Bijou Phillips and DiCaprio dated sometime around 1998, and she credits her ex-boyfriend for getting her a role in the film "Black and White."
DiCaprio was rumored to have had a romantic fling with supermodel Naomi Campbell back in 1995. The two apparently remain friends, and recently partied together on his yacht in Miami.