Gwyneth. Jen. Angelina. Brad Pitt’s dating background needs no introduction. With much more than 30 years together an actor, Pitt—who’s starred in films like The Curious case of Benjamin Button, Fight Club and Ocean’s Eleven—has spent an ext than three years wooing women in Hollywood. (He didn’t host the title of People’s Sexiest man Alive double for nothing.)

But who have been Pitt’s girlfriends (and wives) end the years? of course, as one of the most well-known celebrities in the world, many of us understand a few members of Brad Pitt’s dating history. Yes sir his first wife Jennifer Aniston. Yes his 2nd wife Angelina Jolie. Yet who were the women before and also after his many high-profile relationships? This where our deep dive into Brad Pitt’s dating life comes in. Though Pitt is a family name now, that wasn’t constantly the case. That wasn’t until his big break in 1991’s Thelma & Louise the Pitt shot come the star level we associate him with today.

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This method there to be a entirety side the Pitt’s date life (pre-Thelma & Louise) that most of us don’t also know about. After ~ his divorce native Jolie in 2016, the actor has likewise kept a low-profile once it concerned his romantic relationships. So, without more ado, we current to friend our deep dive into Brad Pitt’s dating history.

Sinitta (1986 – 1988)


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Image: ZUMAPRESS.com / MEGA.


Pitt and also Sinitta, a brothers singer known for the track “So Macho” and appearances top top shows choose I’m a Celebrity…Get Me the end of Here, dated on and off for two years between 1986 and 1988. While she to be on I’m a Celebrity, Sinitta talked about her short-lived romance with the actor, that wouldn’t have his big break in Thelma & Louise until three years after their breakup.

hot. He to be beautiful through the most amazing body. I experienced him for two years,” Sinitta said at the time. “He was fun, he to be young and an extremely sweet. It was before he made Thelma & Louise, however even I observed that movie and also thought, ‘Oh my God, what have actually I done?’”

Christina Applegate (1989)


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Image: Jen Lowery / MEGA.


Applegate and also Pitt didn’t have actually a lengthy relationship. The two were linked when Pitt was the Samantha Who alum’s day to the 1989 MTV video clip Music Awards. In a 2015 interview ~ above Watch What wake up Live, Applegate to be asked about reports that she left Pitt the night for one more man, i beg your pardon she confirmed. Though Applegate didn’t expose who the guy she left Pitt for, she told hold Andy Cohen the he wasn’t an actor. It’s thought that the secret man is singer Sebastian Bach, despite Applegate has yet to check this.

Juliette Lewis (1990 – 1993)


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Image: AP Photo/Reed Saxon.


Pitt met Lewis top top the collection of the film as well Young to Die in 1990 once he was 27. Lewis, for her part, to be 10 years younger than him. The two went on to day for three years and reunite on the 1993 film, Kalifornia. While fostering the film, Lewis told The Los Angeles Time the she and also Pitt were in love. “We’re at the point in love, whereby we as with to watch each various other every solitary day and we don’t obtain bored v each other, for this reason it’s really, yes, really nice,” she said.

In a 2010 interview through The Huffington Post, Lewis looked ago on her relationship with Pitt. “It amazes me that world are still fascinated that us went the end for years,” she stated at the time. “I to be a teenager in ~ the time. The a life time away. I remained in my high institution years, and also it to be a wonderful, loving partnership with a fun, clever guy. Climate it was over, and also he walk on to come to be incredibly famous.”

Gwyneth Paltrow (1994 – 1997)


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Image: PA Wire. Push Association via AP Images.


Paltrow and Pitt to be an “It” pair in the ’90s. The two started dating after they met ~ above the collection of the film Se7en in 1994, three years after ~ Pitt’s large break in Thelma & Louise. While accepting the golden Globe for ideal Supporting Actor for his duty in 12 Monkeys in 1996, Pitt called Paltrow his “angel” and referred come her as the love his life. In 1996, Pitt also proposed come Paltrow, despite the pair didn’t walk under the aisle.

In an interview on The Howard Stern Show in 2015, Paltrow opened up around her connection with Pitt. “I certainly fell in love v him,” she said. He to be so gorgeous and sweet. Ns mean, he to be Brad Pitt! My father was devastated . I was together a kid, ns was 22 as soon as we met. That taken me till 40 to acquire my head the end of my ass. You can’t make the decision once you’re 22 years old. I wasn’t ready, and also he to be too an excellent for me.”

Jennifer Aniston (2000 – 2005)


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Image: RAMEY PHOTO/Mega.


The one where he married Jen. Pitt and Aniston met in 1994 after they were introduced to each other by their managers, who room friends. “He was simply this sweet man from Missouri, you know? A normal guy,” Aniston told Rolling rock in 2001. In ~ the time, Pitt was date Paltrow, so that wasn’t until 1998, a year ~ he and Paltrow had split, the Pitt and also Aniston’s managers collection them up on a date. “Primetime,” Aniston claimed on Diane Sawyers’ Primetime in 2004. “It to be weird…That was a really simple evening. It was really fun.”

Pitt proposed come Aniston in November 1999 on stage at a Sting concert, and also July 2000, the 2 tied the knot in Malibu, California. “I had those usual jitters the day before my wedding, yet the job of, i was simply excited in a great way,” Aniston said Rolling rock in 2001 of your wedding. However, the marital relationship didn’t last. In January 2005, Pitt and Aniston announced that they had damaged up, a year ~ rumors circulated the he had actually cheated on her v Angelina Jolie on the set of Mr. & Mrs. Smith in 2004. The 2 finalized their divorce in October 2005.

“We would favor to announce the after 7 years together we have made decision to officially separate,” Aniston and also Pitt stated in a statement in ~ the time. “For those who follow this sorts of things, us would favor to define that our separation is not the an outcome of any kind of of the speculation reported by the tabloid media. This decision is the an outcome of much thoughtful consideration. We happily stay committed and also caring girlfriend with great love and admiration because that one another.”

In one interview v Vanity fair in September 2005, Aniston opened up around her separation from Pitt. “We exited this connection as beautifully together we entered it,” she said.

In January 2020—after Pitt’s divorce indigenous Jolie and Aniston’s divorce from Justin Theroux—the two rejoined for the very first time in public at the gold Globes. Their reunion come after reports the Pitt and Aniston started texting again and also that Pitt had actually attended Aniston’s 50th birthday party in February 2019. Though the two went on to share a moment at the 2020 death Awards, where they briefly held hands backstage, the 2 didn’t reunite romantically.

Angelina Jolie (2006 – 2016)


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Image: RAMEY PHOTO/Mega.


Pitt and Jolie met top top the collection of Mr. & Mrs. Smith in 2004, if Pitt to be still married to Aniston and also Jolie had actually just filed because that divorce native Billy Bob Thornton. In a 2006 interview through Vogue, Jolie evidenced that she and also Pitt had developed feelings for each other while working on the film. “I think we discovered this strange friendship and also partnership that type of simply suddenly happened. Ns think a couple of months in ns realized, ‘God, ns can’t wait to obtain to work,” she claimed at the time. “It take it until, really, the finish of the shoot for us, ns think, to realize that it might mean something an ext than we’d earlier allowed ourselves come believe. And also both understanding that the reality of that was a huge thing, something the was walk to take a many serious consideration.”

In April 2005, Pitt and Jolie were photographed in Kenya through Jolie’s son, Maddox. Three months later, in July 2005, news damaged that Jolie had embraced her daughter, Zahara, indigenous Ethiopia, with Pitt by her side. In January 2006, Pitt and Jolie confirmed that they were expecting a boy together. They welcomed their an initial child together, Shiloh, in may 2006. A few months later, in march 2007, Pitt and Jolie embraced a son called Pax indigenous Vietnam. In may 2008, Jolie revealed the she to be pregnant through twins. She welcomed the twins, Knox and Vivienne, in 2008.

After year of dating, Pitt proposed come Jolie in April 2012, and the 2 wed in secret in respectable 2014. However, through September 2016, news broke that Jolie had actually filed for divorce from Pitt. She request for primary custody the their 6 children. As of 2020, the custody fight is ongoing.

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Alia Shawkat (2019)


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Image: TPI/MEGA.


Rumors started that Pitt was datign Shawkat, one actor recognized for her duties on reflects like Arrested Development and also Search Party, in 2019 after they were seen on a day at an arts exhibit in Los Angeles. However, in an interview with Vulture in June 2020, Shawkat confirmed that she and also Pitt are not in a romantic relationship. “We’re not dating,” she said at the time. “We’re just friends.”