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Charlize Theron - The romance with Charlize Theron is said to have flourished after the two worked together in an ad campaign for watch brand Breitling.

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Charlize Theron - If #bradlize is for real, Charlize Theron is yet another stunning woman on Pitt's already impressive—and long—list. 

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Neri Oxman - In 2018, it was rumored Pitt was dating world-renowned MIT professor Neri Oxman.

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Neri Oxman - But Oxman denied the rumors in an interview with the New York Times.

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Angelina Jolie - Hollywood supercouple Brangelina met on set while filming 'Mr. & Mrs. Smith' in 2004. Pitt was married to Jennifer Aniston at the time. Nonetheless, Pitt and Jolie eventually went public, and got married in 2014.

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Angelina Jolie - But the couple split up in 2016. They have six children together.

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Jennifer Aniston - Before Angelina Jolie stole Brad Pitt’s heart, he was married to 'Friends' star Jennifer Aniston.

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Jennifer Aniston - The couple started dating in 1998, got married in 2000, but divorced five years later.

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Demi Moore - Before Aniston, Pitt is rumored to have briefly dated actress Demi Moore in 1998.

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Demi Moore - Reportedly, the two have been in contact again following Pitt’s divorce.

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Claire Forlani - Pitt seems to find love at work quite often. Rumor has it that he dated his 'Meet Joe Black' co-star Claire Forlani.

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Claire Forlani - They even attended the 50th Annual WGA Awards together in 1998.

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Sonita Henry - English actress Sonita Henry and Brad Pitt are said to have dated circa 1998.

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Sonita Henry - But neither Pitt nor Henry have confirmed the relationship.

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Gwyneth Paltrow - Brad Pitt and Gwyneth Paltrow also met on set. They got to know each other while filming 'Seven' in 1995.

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Gwyneth Paltrow - But the couple ultimately split up in 1997.

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Thandie Newton - Pitt and actress Thandie Newton met in 1994 while filming 'Interview with the Vampire.'

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Thandie Newton - The couple apparently dated for about a year.

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Julia Ormond - Do you remember the 1994 movie 'Legends of the Fall?' Well, Brad Pitt is reported to have dated his co-star in the film, Julia Ormond.

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Julia Ormond - It’s not known how long the relationship between Pitt and Ormond may have lasted, as they never made it public.

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Geena Davis - Brad Pitt met actress Geena Davis while filming the 1991 classic 'Thelma & Louise.'

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Geena Davis - They too are reported to have had a fling back then.

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Juliette Lewis - Back to a more serious relationship. Brad Pitt and actress Juliette Lewis dated for four years, from 1989 to 1993.

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Juliette Lewis - Pitt was 27 when he started dating the then 17-year-old Lewis.

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E.G. Daily - Pitt and actress E.G. Daily reportedly dated in 1989.

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E.G. Daily - She described him in an interview as a gentle guy who was very down to earth.

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Christina Applegate - Brad Pitt was apparently quite busy dating in 1989. Actress Christina Applegate was another one of his crushes.

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Christina Applegate - The two attended the MTV Movie Awards together, and it's said Applegate ditched Pitt halfway through the date!

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Sinitta - Pitt dated singer Sinitta between 1987 and 1988.

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Sinitta - She is said to have dumped Pitt before he became a Hollywood star.

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Robin Givens - Brad Pitt and model-actress Robin Givens were seeing each other from 1986 to 1987.

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Robin Givens -

But they must have rekindled things, because her famous ex-husband, boxer Mike Tyson, says he caught them in bed together in 1988.

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