Brad Pitt is a genuine Hollywood heartthrob, twice voted the Sexiest Man Alive by People and since his 2016 split from wife Angelina Jolie, he’s single again. With his looks, money, fame, and charm, it comes as no surprise that the list of ladies he’s dated or had a fling with in the past is long.
He’s been engaged twice and married twice, and had many long-term relationships, including high-profile romances with Gwyneth Paltrow and Juliette Lewis. And, over the years, there have been many stories and rumors, some of which have been confirmed, while others remain a mystery to this day.
We’ve scoured published reports to come up with this list of the more surprising women that Brad has been linked to. Hey, with all his advantages, we’re surprised the list isn’t much, much longer. Now that he’s single again, where to next? That’s what the world wants to know.
Brad was the violent dude Tyler Durden in Fight Club and played the charismatic hustler types in Ocean's Eleven, Moneyball, and Thelma & Louise. He's even played off kilter killers in Kalifornia and Snatch, but rocket scientists, not so much. Neri Oxman is a professor at MIT and according to all reports, their six-month relationship was getting serious as of April 2018. Brad was spotted going in and out of her apartment in Cambridge at all hours of the day and night. Neri Oxman, according to her MIT bio, is an architect and designer, and “the Sony Corporation Career Development Professor and Associate Professor of Media Arts and Sciences at the MIT Media Lab, where she founded and directs the Mediated Matter research group.” Sure, we bet she and Brad have many discussions about her projects, which often bring together design, biology, computer science, and engineering. He was even said to have the key to her apartment, but by June 2018, it was clear that it was all over when Neri was spotted with billionaire hedge fund manager Bill Ackerman in Paris.
Back in the 1980s, before social media was there to record it and come up with a cute #couplegoals name, Brad dated pop songstress Sinitta for about two years. Both of them were in their 20s at the time, with their careers just starting out, and from the pics, it looks like the two had a fun-filled relationship. In 2016, Sinitta was asked about Brad – who had just separated from Angelina – on a British TV show, and she joked that he was calling her again. When the host asked about Brad, though, she said, "He is a very good kisser!" Since Brad, Sinitta's been married and divorced to Andy Wilner and palled around with Simon Cowell.
Brad Pitt showed off the looks that would set the silver screen on fire in a photo shoot with actress Shalane McCall back in 1987. It was the year when Brad would snag his first acting gigs on shows like the soap Another World and sitcoms Head of the Class and Growing Pains. He also appeared in four episodes of primetime soap Dallas, during its initial and legendary run. On set, he met actress Shalane McCall, who played Charlie Wade on the show for five seasons. Brad played her boyfriend on the show, and there was a rumored real life romance between the then 23-year-old actor and Shalane, who was only 15 at the time. Shalane went on to marry musician Trent Valladares in 1989 at the age of 17, and subsequently retired from the biz.
Brad got his first major role in a movie in 1989 with Cutting Class, described as a dark comedy slasher flick. (We take it the cutting part isn't really about skipping class.) One of his co-stars was actress Jill Schoelen, who had a bit of a run as a scream queen in 1980s horror flicks like Curse II: The Bite and The Stepfather. The two ended up engaged after dating for a while. They’d been engaged for about three months in 1989 when Jill pleaded with Brad to come visit her on set in Budapest. This is what happened, as Brad told The Sun years later:
“I got there, went straight to the set where she was filming and that night we went out to dinner. She told me that she had fallen in love with the director of the film.
I was so shocked I said, ‘I'm out of here.’”
Brad had a pretty busy year in 1989, including his first bona fide Hollywood movie roles, and, as rumor would have it, a string of girlfriends, and even a three month engagement. That’s packing a lot into one year. Christina Applegate, though, was riding high on the popularity of Married...With Children, which was in its third season. The two apparently dated, but maybe it was Christina’s rising star that got between them. Who knows? What the world does know, is that Christina was Brad’s date to the 1989 MTV Video Music Awards – and she ditched him by the end of the night. Singer Sebastian Bach has claimed in interviews that it was he who left the show that night with Christina. She’s never confirmed that version of events. On the show Watch What Happens Live with Andy Cohen in August 15, though, Christina finally admitted to the incident, although she said it was a non-celeb. The move ended their relationship, not surprisingly.
Elizabeth Ann Guttman a.k.a. E.G. Daily has played in a number of movies since her debut on the silver screen in 1978. She's perhaps best known for playing Dottie in Pee-wee's Big Adventure, and voicing characters like Buttercup in The Powerpuff Girls. In 1989, she apparently became one of the many, many women that Brad dated that year. At the time, Brad never talked about any of the rumors, but in an interview with The Daily Mail in September 2016, she came to his defence. A
t the time, he'd just split with wife Angelina Jolie, and E.G. made a point of going on the record to say what a "gentle guy" he was.
From my experience with him, he was a very down-to-Earth man, she said. E.G. says the two remained close for years after their split.
Brad’s real breakout role came in the 1991 buddy movie Thelma & Louise. In it, he plays the swaggering hustler who sweet talks his way into Geena Davis’ bed and then robs her while she sleeps. But, before she wakes up, the two of them light up the screen with one of movie history’s most talked about intimate scenes. In the movie, the relationship was a one-night stand, but there were rumors at the time that Geena and Brad enjoyed each other’s company off screen as well. Neither actor has confirmed those rumors, even years later. But, in 2014, actor Jason Priestley came out with his memoir. It turns out that Priestley and Pitt were roommates back in the day when both were struggling. He says that Brad and Geena, who had just split from hubby Jeff Goldblum, had a relationship that lasted at least as long as the movie shoot.
Brad co-starred in the 1994 hit Interview With A Vampire with Tom Cruise. It was a meaty role in a popular movie, but ever since then, Brad hasn't had much good to say about it in interviews. In 2011, he told Entertainment Weekly that he looked miserable in the movie for a very good reason. “I am miserable.” He told the interviewer that the only bright spot of the shoot was the city is was filmed in. “The great thing that came out of that movie is that it birthed my love affair with New Orleans.” But, if the rumors are true, there was one other aspect of working on the set that found his favor – British actress Thandie Newton. Thandie played the role of Yvette, who was a servant to Brad’s character Louis. In fact, there’s a scene where he kills her in the movie. Off set, though, we’re told that the two had a relationship that lasted pretty much as long as the shoot.
Brad had a relationship with actress Juliette Lewis that lasted about four years, and began when Juliette was only 16. But, it seems like Pitt doesn't like to be single for very long – in fact, you could call him a chronic serial monogamist. He split with Juliette about February 1993, and it wasn't long before he was photographed with stunning Czech model Jitka Pohlodek. At the time, Brad owned a mansion in the Hollywood Hills that was almost a century old, and Jitka was known to have spent a lot of her time there for about a year. Their household included Jitka's two pet bobcats, Brad's three dogs, and a bunch of chameleons and iguanas. While it sounds like domestic bliss, when Vanity Fair interviewed him in November 1994, while he was still dating Jitka, he told the reporter that he was still in love with Juliette.
“I still love the woman.
The problem is, we grow up with this vision that love conquers all, and that’s just not so, is it?”
Brad and Gwyneth Paltrow had a much publicized relationship that lasted from 1994 to 1997, and we'll just point out that the two met on the set of the movie Se7en. After the two split up, Brad began filming Meet Joe Black, co-starring Anthony Hopkins and British actress Claire Forlani. We'll point out that Ms. Forlani also has a history of dating co-stars, including Ben Stiller and John Cusack. Brad and Claire were often photographed together, and they attended the 50th Annual WGA Awards together as dates. The tabloids went crazy with the theory that Claire had actually broken up Brad's engagement with Gwyneth, and she went from actress with a budding career to tabloid fodder overnight. We'll never know what really happened, but if a relationship did blossom, we're betting the media scrutiny is what put it to a quick end.
In 2005, foxy model April Florio had an interview with Us Weekly. She told the reporter about a relationship she'd had with Brad Pitt in 2003. According to the Us Weekly story, April said that she's met Brad after being introduced by pal George Clooney. According to her story, Brad "was attracted to me," and complained that he was bored with his marriage to Jen.
"He hated the fact that his wife liked to hang with her friends or just stay home. He liked to go to parties more."
At the time ,April was 22 and Brad 41. She said – and her agent confirmed – that she had spent three days in Greece with Brad, and that he'd bought her a plane ticket to Los Angeles. When the story hit the media, however, April tried to back out completely, claiming that she'd only bumped into him at a party, and that the reporter had misrepresented her words. Brad, as per usual, denied it all. But, the reporter said the whole thing was on tape.
In 1998, Demi Moore was going through a very public and pretty nasty divorce with Bruce Willis. During that time, the rumors flew that she and Brad Pitt were hooking up. The fling was said to be hot, but over pretty quickly. In March 2018, the rumors about Demi and Brad flew again. According to a report in RadarOnline, Brad, still despondent about his divorce from Angelina, had reached out to Demi in desperation. Demi was said to be drawing him into Kabbalah, the esoteric philosophy inspired by Judaism that Demi, Madonna and other celebs subscribe to. Another story in the National Enquirer said the two were practicing "sensual yoga" together. But, according to GossipCop and E!Online, the recent rumors aren't true. Now about 1998? We'll never know for sure.
“I think Brad has something very special. Apart from the fact that he’s a gorgeous guy, he’s also someone who’s constantly trying to shrug that off.
He’s not egotistical. He’s very, very careful with people, and sweet.”
That’s what Julia Ormond told a reporter in 1995 about her Legends of the Fall co-star. The movie had just come out, and Julia had nothing but good things to say about Brad. Rumors flew around the set and in the media that Julia and Brad were practicing their love scenes in the movie for real. Julia was married at the time, although she divorced her husband in 1994, and neither has ever confirmed the rumors.
Brad's alleged relationship with British actress Sonita Henry is reported to have happened in 1998. If it happened, it would have been more of a hook-up than a relationship. There were many rumors about Brad and Sonita, who was just beginning her acting career at the time. Neither has confirmed the rumors or even discussed them. If it's true, then it would have happened during Brad's post-Gwen and pre-Jen dating period, and it would make sense – although we’re curious how these two might have met. Sonita's never gotten to the A-list, unlike Brad, but she's carved out a name for herself in the sci-fi world with roles in Star Trek, Doctor Who, and others.
When Brad Pitt worked opposite actress Robin Givens on the set of sitcom Head of the Class in January 1989, she was technically still married to boxer Mike Tyson. In 2012, Tyson went on Conan to try out some material for his one-man show, and one of the anecdotes was about Robin and Brad. Tyson says that he dropped by Robin’s place one morning in February 1989, hoping for a quick booty call on his way to the divorce lawyer. But, when he saw Brad in her kitchen, he knew the chances of any carnal relations with his soon to be ex were dashed. It became a favorite story that Mike would bring up in many interviews. In 2016, he told The Real, “I didn't really catch them in the act — maybe before the act. He's a really nice guy.”