Brad Pitt’s Dating History: His Ex-Wives, Girlfriends, and Flings

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It’s no secret that Brad Pitt has a long history of dating and romance. We all know his more famous relationships like Gwyneth, Jen, and Angelina — but you may not know all the names William Bradley Pitt Brad Pitt has dated, bedded, or been linked with. So, without further ado, let’s get to know all the women in Brad’s life, from his 1980s crush on an English pop singer to his current partner.

Sinitta

In the 1980s, Brad Pitt spotted British singer Sinitta on TV, fell in love, and had his agent introduce them. In a 2011 episode of I’m a Celebrity … Get Me Out of Here, Sinitta claimed she dated Brad from 1984 to 1986.

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She also told Marie Claire, “He was stunning, had an incredible physique. We were together for two years. He was enjoyable, youthful, and genuinely kind.” The “So Macho” singer later dated Simon Cowell and alleged Brad chased her after he split with Angelina. Yeah, right!

Shalane McCall

Did you know Brad Pitt appeared in the 1980s Texas oil tycoon soap opera Dallas? No, nor did we until we looked it up. In 1987, the 24-year-old actor allegedly had an eyebrow-raising relationship with his then-co-star, Shalane McCall. It turned a few heads, considering that Shalane was 11 years Pitt’s junior.

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McCall was Pitt’s first on-screen kiss, and seems to have put her off acting for life! Of course, we’re only kidding. Still, while it may not have been Pitt’s fault, McCall did give up acting the following year, making her last on-screen appearance in a 1988 episode of The New Leave it to Beaver.

Robin Givens

If there’s one woman you don’t want to get involved with, it’s Mike Tyson’s wife. But, Bradley went there anyway. He met Robin Givens on an episode of Head of the Class when the actress was divorcing Iron Mike between 1988 and ’89. The fearsome boxer once claimed he caught his ex in a compromising position with Pitt.

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However, Givens insisted that “never, ever happened.” However, Tyson did catch them canoodling in a car, which Givens confirmed on Watch What Happens Live With Andy Cohen in 2019.

Jill Schoelen

Pitt met Keanu Reeve’s ex-girlfriend, Jill Schoelen, on the set of 1989’s dark comedy slasher movie Cutting Glass. They even got engaged, but then, “She told me that she had fallen in love with the director of the film. I was so shocked. I said, ‘I’m outta here.'”

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Brad told the UK newspaper, The Sun. When Radar Online interviewed Jill Schoelen in 2013, she said Pitt was a “deep and soulful” man who wrote her “the most beautiful poems” during their “beautiful” but short-lived time together.