Brad Pitt's Dating History: Jennifer Aniston, Angelina Jolie and More

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Sinitta: 1986 – 1988

Brad dated Sinitta on and off for two years from 1986 to 1988. The British songstress, who also dated Simon Cowell, divulged about their relationship on TV show I’m a Celebrity… Get Me out of Here! in 2011. “[He was] hot. He was beautiful with the most amazing body. I saw him for two years,” Sinitta explained, per Daily Mail.

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Robin Givens: 1986 – 1987

Brad was linked to actress Robin Givens following her divorce from Mike Tyson around 1986. The professional boxer joked about his failed marriage in an interview with Conan O’Brien in 2012.

“Brad Pitt is the international symbol for [divorce],” he quipped at the time.

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Shalane McCall: 1987 – 1988

Although never confirmed, it was speculated Shalane McCall dated Brad after the two met on the set of TV show Dallas.

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Christina Applegate: 1989

The Troy actor accompanied Christina Applegate as her date to the 1989 MTV Music Video Awards, but she actually left him for another guy! The Dead to Me actress once opened up to Andy Cohen about their first date, but refused to dish who she left Brad for!

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Jill Schoelen: 1989

Brad was once engaged to his Cutting Class costar Jill Schoelen for three months in 1989, but the two sadly cut it off not long after.

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E.G. Daily: 1989

Voice actress E.G. Daily and Brad briefly dated in 1989 before calling it off. In a 2016 interview with the Daily Mail, E.G. opened up about her famous ex-boyfriend. “He was never someone that was super Hollywood, he was a very calm and gentle guy,” she told the outlet.

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Juliette Lewis: 1989 – 1993

Besides Ang and Jen, Brad’s relationship with Juliette Lewis is considered of one of the actor’s longest. The couple began dating in 1989 when Brad was 27 and Juliette was 17. In 2014, she opened up to HuffPost Live about her high-profile romance.

“It amazes me that people are still fascinated that we went out for four years,” she said at the time. “I was a teenager at the time. It’s a lifetime away. I was in my high-school years and it was a wonderful, loving relationship with a fun, smart guy. Then it was over and he went on to become incredibly famous.”

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Geena Davis: 1992

Many though Brad and Geena Davis were just on-screen lovers in Thelma & Louise, but it seems the two pursued a relationship in real life! Brad’s former housemate, Jason Priestley, once dished that they also had a brief off-screen relationship, according to Harper’s Bazzar.

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Thandie Newton: 1994

Although his relationship with Thandie Newton wasn’t confirmed either, the two reportedly dated around 1994.

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Jitka Pohlodek: 1994

Although nothing seemed to come of it, Brad brought Czech model Jitka Pohlodek as his date to the premiere of his 1994 film Legends of the Fall.

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Gwyneth Paltrow: 1994 – 1997

Gwyneth Paltrow was one of Brad’s first high-profile romances. The gorgeous couple dated for a few years from 1994 to 1997. Although it didn’t work out, Gwyn eventually found love with new husband Brad Falchuk!

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Claire Forlani: 1998

Brad briefly dated Claire Forlani after the two starred alongside each other in Meet Joe Black in 1998. They dated for a little while before calling it quits.

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Jennifer Aniston: 1998 – 2004

Brad and Jen first met in 1998 after the two were set up on a blind date by their agents. The Ken and Barbie of Hollywood tied the knot in 2005, but sadly separated in 2005 and finalized their divorce later that year.

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Angelina Jolie: 2005 – 2016

Brad and Angelina first began dating in 2005 after the former lovebirds met and fell in love on the set of Mr. & Mrs. Smith. The two quickly became attached at the hip.

The couple married in 2014 and became parents to six kids — Maddox, 18, Pax, 15, Zahara, 14, Shiloh, 13, and 11-year-old twins Vivienne and Knox — before filing for divorce in 2016.

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Brad Pitt's Girlfriend Nicole Poturalski

Nicole Poturalski (2019 – Current)

Brad and Nicole were first spotted together in November 2019 at a Kanye West concert in Los Angeles. Nearly one year later, the Oscar winner was smitten with the German model and things seem to be heating up.

Brad is “confident” his six children “will love” Nicole, an insider told Closer Weekly on August 27. Nicole has a son who she adores and is amazing with kids, which Brad finds super attractive. They haven’t reached the milestone where he’s introduced her to his brood, but he’s thought about it.”