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

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.

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!

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.

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.

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.

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.

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.'”

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.

Actress and singer Elizabeth “E.G.” Daily” also dated Brad between 1989 and 1990 before his breakthrough role in Thelma and Louise. And Brad’s certainly got a way with the ladies! When E! ‘s True Hollywood Story interviewed her about their short-lived romance in 2021, she too described Pitt as “deep-souled.”

She went on to say, “I think he was really intense about his work. When you saw him, it was more like seething in him underneath. What I could feel from him was a really strong, visceral drive toward something really big.”

1989 was a busy year for Brad. One of his many girlfriends that year was Christina Applegate, the young actress who played the girl every teenage boy was in love with, Kelly Bundy from the popular late-1980s sitcom Married… With Children.

The pair met at the MTV Movie Awards and allegedly dated for a short time. And it seems it was a very short time as Applegate quickly dumped Brad for another guy. As for who that lucky guy was, it remains a mystery.

When Brad Pitt made 1989’s Too Young to Die?, he started dating his 17-year-old co-star Juliette Lewis. The Yellowjackets actress once opened up about their deep connection, and Pitt told Vanity Fair magazine that their relationship was one of his greatest, adding, “I still love the woman” and “had a great time with her.”

The relationship lasted four years until 1993 — the year they made Kalifornia together. The moral of the story? Never work with animals, children, or your partner!

Brad’s break-out role came in 1991’s Thelma & Louise. He quickly became Hollywood’s hunkiest heartthrob and has never looked back. But while he was making the movie, he filmed a steamy love scene with his stunning co-star, Geena Davis. The pair secretly saw each other for a year after the movie wrapped before the relationship went off a cliff.

Brad’s former roommate, Beverly Hills 90210 star Jason Priestley, confirmed the rumors and told The Hollywood Reporter that Geena Davis made sure their meetups were conducted in secret.

Brad and English actress Julia Ormond played lovers in the 1994 epic Western drama Legends of the Fall. And that’s not all they did! On-set rumors said the pair spent a lot of time together in each other’s trailers. However, neither party ever acknowledged their relationship publicly.

So, you might think that by the time the Legends of the Fall movie premiere rolled around in 1994, he might have asked Julia Ormond to accompany him as his date. But remember — this is Brad Pitt we’re talking about!

In 1994, long-haired, bleach-blond Brad showed up to the Legends of the Fall premiere looking like Floyd from True Romance — but with a stunning brunette on his arm. She was American model and actress Jitka Pohlodek. What do you mean you’ve never heard of her? She played Bar Girl 2 in Sugar: The Fall of the West.

While they never publicly spoke about their brief romance, Pohlodek once gushed in an interview that Pitt “glows.” And since he glows, he beat Edward Cullen to become the first sparkly vampire.

When Brad played vampire Louis de Pointe du Lac in Interview With the Vampire, 22-year-old British actress Thandie Newton became the latest gorgeous actress to fall under his hypnotic gaze. They met on the set of the vampire movie in 1994 and dated for a year.

Thandiwe — or Thandie as she was known for 25 years due to a credits typo — split up amicably with Brad in 1995, and the two have remained friends ever since. They’ll always be friends because, as vampires, they’re immortal.

Next up, 32-year-old Brad met a young actress by the name of Gwyneth Paltrow. She played his doomed wife in David Fincher’s excellent thriller Se7en (1995). After wrapping the production, the pair turned their on-screen chemistry into real-life love.

Everyone loved the fact they were together, and their relationship was so serious that they even got engaged the following year. They dated between 1994 and 1997, and ever-romantic Brad popped the question on the balcony of a house they rented in a little Argentinian town.

The celebrity couple were the darlings of Hollywood for three years and it was obvious they were very much in love. In his speech at the 1996 Golden Globes, Brad referred to Gwyneth as “my angel” and “the love of my life.”

Hollywood’s hottest couple held an extremely public relationship and graced the cover of every magazine imaginable. But, their engagement wouldn’t last. In 1997, after being betrothed to Bradley for a year, Gwyneth suddenly called off the engagement. But why? Are you insane, woman?

In 2015, Gwyneth told Howard Stern, “He was so gorgeous and sweet. I mean, he was Brad Pitt! My father was devastated. I was such a kid; I was 22 when we met. It’s taken me until 40 to get my head out of my [butt]. You can’t make that decision when you’re 22 years old. I wasn’t ready, and he was too good for me.”

You could say that Gwyneth lost her head. That’s a Se7en joke. During a 2023 interview on the Call Her Daddy podcast, Gwyneth said that she and Brad are still friends.

Brad Pitt can be a bit of a devil, so he was the perfect choice to play the Grim Reaper in Meet Joe Black. After the love of his life dumped him in 1998, Pitt is rumored to have had a fling with his Meet Joe Black co-star, Claire Forlani.

The beautiful English actress walked hand in hand with Pitt on the red carpet for their movie premiere, and the word on the street is that they were seeing each other. But, like most of Bradley’s relationships, it didn’t last long.

Brad reportedly had a very brief thing going on with Demi Moore in 1998. The G.I. Jane actress had only recently split from her husband, Bruce Willis, in June ’98 — and they didn’t file for divorce until October 2000.

That means Brad was seeing Demi while she was still married to the Die Hard star. It didn’t come to fisticuffs, but our money is on Bruce Willis in a fight. That said, Demi Moore could have beaten them both!

Hold on to your hats because this is where things start getting bumpy! In 1998, Brad went on a “blind” date with Jennifer Aniston after being set up by their agents. That is, if there’s such a thing as a blind date with one of the most recognizable faces on the planet, thanks to her work on Friends.

The two married the next July in a grand Malibu wedding with 200 guests and 50,000 flowers! The two were together for five years, but then Brad played away from home again.

Brad met another woman while making the spy thriller Mr. & Mrs Smith in 2003. He and his equally famous co-star fell in love but stated there was no infidelity. Pitt and Aniston announced their separation in January 2005.

Jen filed for divorce two months later, and the divorce came through that October, marking the end of their seven-year relationship. Luckily for Jen, a few years later, she met equally hunky actor Justin Theroux. She and The Leftovers star met in 2007 and married him in 2015… but that marriage only lasted two years.

The other woman Brad met on the set of Mr. & Mrs Smith was Angeline Jolie. Pitt unceremoniously kicked Jen to the curb to shack up with Jolie. Shortly after, Jolie told Vogue magazine, “I didn’t know much about exactly where Brad was in his personal life. But it was clear he was with his best friend, someone he loves and respects.”

She continued, “It took until, really, the end of the shoot for us, I think, to realize that it might mean something more than we’d earlier allowed ourselves to believe.”

Brad and Angelina, or “Brangelina” as the media called them, quickly became Hollywood’s most prominent power couple. Their good looks and philanthropy made them the talk of Tinseltown, and they based their marriage on a deep, spiritual bond and mutual philanthropy.

Together, they welcomed three biological children and adopted another three. The handsome couple finally walked down the aisle in 2014, but their marriage wouldn’t last…

Brangelina remained Hollywood’s most famous couple for 13 years. Between 2003 and 2016, they appeared to the world as a loving, committed couple and caring parents. However, that year, Jolie claimed Pitt got physical with both her and one of their children on an airplane.

She filed for divorce in September 2016. In a GQ interview, Pitt spoke of the toll the divorce has taken on his family, saying, “It’s just very, very jarring for the kids to suddenly have their family ripped apart.” You should have thought of that earlier, Brad.

After Brangelina went their separate ways, Pitt was rumored to be dating architect and MIT professor Neri Oxman in April 2018. A source explained, “It took him a long time to date, but he is now. He likes women who challenge him in every way, especially in the intellect department.”

However, less than six months later, Neri denied they were ever an item but called Brad “the last of the Mohicans in post-Netflix Hollywood […] He brings together the timely and the timeless, which is what cinema is all about.”

After separating from Angelina, paparazzi snapped photos of Brad lost in conversation with Sienna Miller at a Lost City of Z dinner event in Los Angeles. Rumors they were an item swirled when an insider revealed to Us Weekly that Brad and the British model and actress were “spending some time together.”

Two months later, Brad and Sienna were spotted with Bradley Cooper at England’s Glastonbury Festival, adding more fuel to the fire pit. That said, there’s been no confirmation Pitt and Miller ever officially dated.

In 2019, tabloids linked Pitt to jewelry designer, holistic healer, and ex-Red Hot Chili Peppers touring nurse Sat Hari Khalsa (pictured, left). They were spotted together at an afterparty of Pitt’s Ad Astra movie premiere. Us Weekly wasted no time revealing the 56-year-old actor was dating the 50-year-old.

However, neither party ever confirmed the reports, and E! Online said the rumors were not true, so they could just be friends. In 2022, Brad and Sat Hari Khalsa launched a new luxury cashmere line called God’s True Cashmere.

William Bradey and German model Nicole Poturalski first met at a 2019 Berlin Film Festival party for Once Upon a Time … in Hollywood. One witness noted, “They were very flirty.” In August 2020, paparazzi spotted them at Château Miraval in France, where an industry insider said they were “enjoying each other’s company while traveling.”

A friend revealed that Nicole was a good match for the 56-year-old actor, saying, “I like her a lot. She has spunk. She’s smart. If she’s dating Brad, good for her. Good for him!”

However, in October 2020, a spokesperson revealed to People magazine that the unofficial relationship was “totally over,” explaining, “Brad hasn’t seen Nicole since August. It was never a relationship. They saw each other a few times, and that’s it.”

The source continued, “You can’t call it a split because they were never together in the first place. It was a casual fling, and that’s it.” Yet by the time 2022 rolled around, the same publication revealed that Brad “still keeps in touch” with the stunning model.

As soon as English-born American model Emily Ratajkowski split from her husband — actor and producer Sebastian Bear-McClard — Brad Pitt pounced. A source close to Ratajkowski said she was not looking to jump into a serious romance.

She added, “It’s the perfect timing right now. There is nothing like Brad Pitt cheering you up. She wants to get to know him better.” People magazine that they are “spending a lot of time together,” though “friends aren’t sure if it’s serious,” and the two don’t “appear to be ‘dating’ formally.”

A month later, a clearer picture of their relationship emerged. It turned out to be a fun and casual romance. A source close to Pitt confirmed that Emily Ratajkowski “Has the vibes that Brad likes. She’s bright and articulate.”

Another source added, “They have a lot to talk about and always have a great time when they hang out. There is an attraction, but nothing serious is going on. They have had a few dates and stay in touch when they don’t see each other.”

So, who’s Brad dating right now? Well, in early 2022, jewelry designer Ines de Ramon split from her husband, The Vampire Diaries actor Paul Wesley, and yet again, Brad Pitt pounced. She must have a thing for vampires, as Brad played a bloodsucker in Interview with a Vampire.

Journalists first spotted Pitt and de Ramon together at a Bono concert in Los Angeles in November 2022. They met through a mutual friend, and after dating for a few months, Brad was “really into” de Ramon… who’s 29 years his junior.

The same month, a source close to Pitt revealed, “It’s not an exclusive relationship,” but “Brad enjoys spending time with her.” However, four weeks later, Ines accompanied Brad to the Los Angeles premiere of his film Babylon. They also spent Brad’s 59th birthday — December 18th — together at an Italian restaurant in Hollywood.

Witnesses noted their closeness and declared the two were “in love.” Cut to present day, and Brad has started introducing Ines as “his girlfriend.” The lovebirds look to have a stable and steady thing going on. Sorry, ladies!