The Fight Club actor was married to the FRIENDS alum from 2000 to 2005, and the two have remained good friends ever since.
Brad Pitt and Jennifer Aniston were one of the most popular couples in Hollywood in the early 2000s before the couple called it quits after Pitt allegedly cheated on Jen with his Mr. and Mrs. Smith co-star Angelina Jolie. Aniston then married long-time beaux Justin Theroux, only for the couple to separate a few years after.
Reportedly, their managers introduced Brad to Jennifer, and the two started dating way before exchanging wedding vows in a lavish ceremony in 2000.
“We both [knew] on our first date, it was a “really easy evening … really fun,” Aniston told Diane Swayer in an interview in January 2004.
The power couple made their relationship official in 1999 when they made their red carpet debut as a pair at the 51st Primetime Emmy Awards.
According to Us Weekly, they also crashed a Sting Concert in New York City, where Jennifer showed off her engagement ring the same year.
The couple tied the knot on July 29, 2000, in a grand ceremony in Malibu.
In February 2004, the Murder Mystery actress told The Guardian she was ready to have a baby and could work out pregnancy.
“It’s time. It’s time. You know, I think you can work with a baby, I think you can work pregnant, I think you can do all of it,” she said. “So I’m just truly looking forward to slowing down.”
Three months after Aniston hinted at the couple’s intentions of starting a family, Pitt crossed paths with Angelina Jolie on the set of Mr. and Mrs. Smith.
Months later, Jen and Brad announced their separation in a joint statement after the Bullet Train actor sparked cheating rumors with Jolie.
“We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration,” the joint statement read.
“We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months.”
Two months after announcing their split, Jennifer filed for divorce from Brad in Los Angeles Superior Court.
“Her court papers cited irreconcilable differences, PEOPLE reported. She also requested to restore her last name from Pitt back to Aniston. The divorce was finalized later that year on Oct. 2,” per PEOPLE.
In September 2005, Aniston sat down in an interview with Vanity Fair and opened up about her failed marriage with Pitt.
“There are many stages of grief,” she said. “It’s sad, something coming to an end. It cracks you open, in a way — cracks you open to feeling. When you try to avoid the pain, it creates greater pain. I’m a human being, having a human experience in front of the world. I wish it weren’t in front of the world. I try really hard to rise above it.”
Talking about her reaction to Pitt and Jolie’s vacation photos from their Kenya trip, before which they had denied romance rumors, Jennifer said,
“I can’t say it was one of the highlights of my year,” she told the outlet. “Who would deal with that and say, ‘Isn’t that sweet! That looks like fun!’? But s— happens. You joke and say, ‘What doesn’t kill you makes you stronger.’ “
“I would much rather everyone move on. I am not defined by this relationship. I am not defined by the part [the media is] making me play in the triangle. It’s maddening to me.”
In 2007, Pitt told V Magazine that he and Aniston were still close despite their split.
“Jen and I still maintain a deep friendship and have a lot of life together that isn’t erased in any way,” he said.
“I don’t know how better to have handled [it]. My view was, this was no one’s business in the end — at least in matters of the heart. The thing guiding me then was, you don’t know how many days you have, and you need life to be everything you need it to be.”
In 2011, Pitt spoke to Parade about his marriage with Jen and said he was not living an interesting life with her.
“It became very clear to me that I was intent on trying to find a movie about an interesting life, but I wasn’t living an interesting life myself. I think that my marriage [to Aniston] had something to do with it. Trying to pretend the marriage was something that it wasn’t,” he said.
In 2014, the Fury star married Angelina at their estate in France.
A year after his second marriage, Aniston also tied the knot for the second time and married Justin Theroux.
However, both marriages didn’t work, and the two divorced their second spouses.
Pitt and Jolie parted ways in 2016 after two years of marriage, and Aniston and Theroux split in February 2018 after three years together.
In 2019, Jennifer told Elle that although both of her marriages failed, they were still valuable.
“My marriages, they’ve been very successful, in [my] personal opinion,” she said. “And when they came to an end, it was a choice that was made because we chose to be happy, and sometimes happiness doesn’t exist within that arrangement anymore.”
On the other hand, after his split with the Salt actress, Brad Pitt took some time off to focus on his mental and physical health and even entered therapy.
A source close to the star revealed that the Legends of the Fall actor regretted leaving Aniston and said ‘it was the biggest mistake of his life.’
“He’s come to realize that leaving Jen for Angelina was one of the biggest mistakes of his life. And while Brad’s not in love with Jen, he realizes how much he does love her. Brad keeps telling friends that he’s seeing everything more clearly,” the source revealed, adding that the actor wouldn’t dream of ruining any relationship she’s in but wouldn’t think twice if he’d ever got a second chance with her.
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Sources: PEOPLE – The Guardian – Vanity Fair
