Actor Leonardo DiCaprio has fulfilled the dream of dating America’s most attractive women by far. For years DiCaprio has been linked to major supermodels whether it be rumored hookups or serious relationships. After his most recent breakup with Victoria’s Secret model, Erin Heatherton, it’s safe to say that DiCaprio has added yet another beautiful woman to his list of past supermodel girlfriends.

Erin Heatherton – (December 2011-October 2012)
DiCaprio dated Victoria’s Secret model Erin Heatherton since late 2011. After nearly a year of dating, the two have recently called it quits. Reports have suggested that the couple’s busy schedules prevented the two from continuing their romance. With DiCaprio starring in The Great Gatsby, he has been spending months away from home for filming. While the once happy couple has decided to end their relationship, it has been suggested to be a clean breakup.

Bar Refaeli (2005-2011)
DiCaprio had a five-year relationship with Israeli supermodel Bar Refaeli. After calling it quits for a few months in 2009, the couple got back together in 2010 to continue their romance. While the couple tried to keep their relationship low key in their early years, People Magazine reported that during their six-month break up, Rafaeli told the press that their time apart showed her how to not fear being alone. Soon after in 2011, the couple ended their relationship for the second time.

Gisele Bundchen (2000-2005)
Before his long romance with Bar Rafaeli, DiCaprio had another five-year relationship with Brazilian supermodel Gisele Bundchen. During their relationship, the two were seen attending various events together including basketball games, charity events and the Oscars. After things reportedly got rocky between the couple, they decided to end their relationship in 2005.

 Eva Herzigova (1998-1998)
According to reports, Victoria’s Secret model Eva Herzigova dated DiCaprio for a month in 1998. Their romance soon revealed itself as an affair as Herzigova was married to Bon Jovi’s drummer Tico Torres during that time.

Amber Valletta (1998-1998)
DiCaprio had a short fling with model Amber Valletta in 1998 after seeing her in a magazine. The story has been told as simply as that, stating that the recent fame DiCaprio gained from Titanichelped him land Valletta for a short relationship.

Kidada Jones (1998-1998)
During DiCaprio’s year of rumored flings, the actor also reportly dated model and daughter of music producer Quincy Jones, Kidada Jones. After the two were spotted together, rumors of their relationship spread.

Helena Christensen (1997-1997)
For another fling before Valletta, DiCaprio was linked to supermodel Helena Christensen around the premiere of Titanic. According to reports, neither of the two confirmed or denied their romance. The pair was linked only for a short time in 1997.

Kristen Zang (1996-1997)
A young DiCaprio dated American model Kirsten Zang on and off for about a year. At the beginning of his fame, DiCaprio was linked with Zang in the press. The two were spotted at the Romeo & Juliet premiere in Los Angeles in 1996.

Bridget Hall (1994-1994)
His brief encounter with Sports Ilustrated model Bridget Hall in 1994 is now considered to be nothing more than a few hookups.

Bobby Brown
In the early 90s, DiCaprio was rumored to be dating actress and model, Bobby Brown. Brown was known for her role in a music video by Warrant called, cherry Pie.