Ever since his breakout role as an attractive young hitchhiker in “Thelma & Louise,” Pitt has been considered one of Hollywood’s most eligible and sought-after bachelors. As a result, there’s no shortage of women that have been romantically linked to the “Ad Astra” actor over the years.
While fans wait and wonder if anything will crystalize between him and Aniston now that he’s back on the market, it’s worth taking a look back at the many ex-girlfriends Pitt has dated over the years.
Pitt’s first high-profile celebrity romance was with “So Macho” singer Sinitta in 1988. At the time, he wasn’t the household name he is today. She, however, was a successful pop artist.
As the Daily Mail notes, she appeared on Alan Carr’s New Year Specstacular in 2019 where she was asked about her relationship with the actor. She joked that, since his divorce with Angelina Jolie was finalized, he had been calling her to try and rekindle things.
“He has been calling and you know what I said? ‘Brad. Move on.’”
After some unconfirmed dalliances with co-stars, Pitt started dating his “Cutting Class” co-star and they ultimately got engaged. Three months into said engagement, she reportedly requested that he come to visit her on a movie set in Budapest. However, that’s where the actor claims things went awry.
"At this point, I had $800 to my name and I spent $600 of it getting a ticket from Los Angeles to Hungary to see her," Pitt reportedly told The Sun in 2011 (via CTV News). "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 outta here.'"
It would not be the star’s last engagement.
The duo reportedly sparked a romance while he was an actor on Robin Givens' sitcom, “Head of the Class,” in 1989. At the time, she was locked in divorce proceedings with professional boxer, Mike Tyson. Speaking on “Conan” in 2012, Tyson explained that he went over to Givens’ place for a rendezvous one morning, despite their breakup, only to find Pitt at his estranged wife’s home. The story eventually made its way into Tyson’s one-man show. Fortunately, it doesn’t seem like he was jealous enough to show Pitt his boxing skills at the time.
This romance was particularly short-lived. Applegate brought Pitt to the 1989 MTV Movie Awards as her date. However, she previously said that she ditched him in the middle of the night for an unknown guy.
The actress appeared on “Watch What Happens Live” in 2015, where she was asked directly about the incident and confirmed that she did indeed ditch Pitt on a date, but refused to give any further details on the matter, specifically who the mystery man was.
Pitt is said to have briefly dated the acclaimed voice actress for a brief time before he started a more serious romance with another woman. Daily spoke about their past relationship in an interview with The Daily Mail in 2016 where she described him as a “laid-back” person.
“He's in a whole other realm. Brad does a lot of Hollywood stuff, but he's not a Hollywood guy. From my experience with him, he was a very down to earth man.”
Pitt’s former roommate Jason Priestley revealed in his 2014 tell-all memoir that the actor’s steamy sex scene with Davis in “Thelma & Louise” morphed into a real-life off-screen romance. However, he was mum about further details.
At the time, Davis was splitting with her husband, Jeff Goldblum.
Pitt starred alongside Juliette Lewis in the films “Too Young to Die?” and “Kalifornia.” While working together, they began a romance that lasted about three years. They even lived together before they broke up.
He explained to Vanity Fair in 1995 that he still had feelings for her, but they both agreed to split.
“I still love the woman. There’s some real genius there. I had a great time with her,” Pitt told the outlet. “Look, I don’t want to go into an explanation. She has her own views, and I respected those views. She does know people. It was one of the greatest relationships I’ve ever been in. The problem is, we grow up with this vision that love conquers all, and that’s just not so, is it?”
Pitt dated Paltrow after they met on the set of the 1995 thriller “Se7en.” In December of 1996, he popped the question and she said yes. However, before they could tie the knot, the duo called it quits in 1997.
In 2015, Paltrow, who was 22 at the time of their engagement, spoke on Howard Stern’s show where she opened up about their whirlwind romance and put most of the blame for things ending on herself.
“I think I was a kid and I wasn’t ready. He was too good for me,” she explained. “I honestly do think, I was too young and didn’t know what I was doing.”
Pitt and the “Friends” star began dating in 1998 and started dating after their managers, who were friends according to Rolling Stone, set them up on a date.
The night went well and by 1999 they were one of Hollywood’s most-sought-after A-List couples. Pitt proposed later that year. Unlike Pitt's previous engagements, this one stuck and the duo wed in 2000. Unfortunately, things wouldn’t last in what remains one of the most shocking Hollywood breakups in recent memory.
Pitt and Aniston broke things off in 2005 after the actor had an affair with his “Mr. & Mrs. Smith” co-star, Angelina Jolie. Aniston moved on with celebrities like Vince Vaughn and Bradley Cooper and even married “Leftovers” star Justin Theroux in 2015, only to divorce again in 2018.
Pitt and Jolie's romance heated up fast. In 2005, he accompanied her to Ethiopia where she adopted her second child. In 2006, he formally adopted all three of Jolie's adopted children. They also welcomed three biological children together.
The duo finally married in 2014 after falling for each other a decade earlier while filming "Mr. and Mrs. Smith." Although Jolie marked Pitt’s longest relationship to date, things ultimately didn’t last.
They announced their separation in 2016 and finalized their contentious divorce in 2019.