Aniston and Pitt were introduced by their managers in the mid-'90s, years before their relationship turned romantic. "He was just this sweet guy from Missouri, you know?" Aniston later recounted to of her first impression of her future husband. "A normal guy."
With both Aniston and Pitt newly single — she split from actor and he recently called off his to — their managers brought them together once again. This time, they hit it off.
"That was a really easy evening.
It was really fun," Aniston later of their immediate chemistry.
The couple kept their romance under wraps for the first few months, before making their highly-anticipated red carpet debut at the 1999 . The duo hit the carpet in particularly memorable looks, with Pitt wearing a pair of silver sunglasses and Aniston in a sequined dress.
During a concert at New York City's Beacon Theater, the couple took the stage to show off Aniston's new bling: a diamond-and-platinum engagement ring from Italian jewelry designer Silvia Damiani, which that Pitt spent seven months helping design.
Surrounded by 200 of their friends, family and costars, the couple — with Aniston promising to always make Pitt's "favorite banana milk shake" — beside the beach in Malibu, California. The lavish nuptials featured 50,000 flowers, four bands, a 13-minute fireworks display and more.
The bride wore a silk-and-satin beaded gown by Lawrence Steele for the special day. Event planners estimated the wedding day may have cost $1 million.
Just one year after their initial red carpet debut, the duo stole the spotlight when they arrived at the 2000 , marking their first red carpet appearance as husband and wife.
The actor memorably joined his then-wife on-screen for the first time in the Thanksgiving episode of season 8 of , "The One with the Rumor." He played Will Colbert, who launched an "I Hate Rachel Green Club" in high school. Aniston later revealed that he was , saying, "Mr. Pitt was wonderful."
The couple served up another iconic red carpet look with their matching moment at the 2002 Golden Globes, where Aniston was nominated for the first time.
The duo coordinated in black suits and their signature blond highlights.In 2002, Aniston and Pitt co-founded Plan B Entertainment alongside producer Brad Grey. "We started this little company underground, didn't really talk about it because we didn't want to be accused of being actors who have vanity deals where you don't do anything," Aniston told in 2004.
Soon, things "snowballed" and the company had 17 films in production, including 2004's (starring Pitt) and 2005's . When the pair split in 2005, Pitt became the company's sole owner, with Grey leaving to head up Paramount Pictures.
During an interview with in which the interviewer referred to Pitt as the love of Aniston's life, the actress responded that she wasn't a big fan of the phrase.
"Is he the love of my life? I think you're always sort of wondering, 'Are you the love of my life?' I mean, I don't know, I've never been someone who says, 'He's the love of my life.' He's certainly a big love in my life … ," she told the outlet. "And I know that we have something special, especially in all this chaos. In this nutty, brilliant, wonderful, hard business that we have, it's nice to have somebody who's anchored and knows you, really knows all of you.
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Speaking to , the Along Came Polly star revealed that she was ready to start a family with Pitt. "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. So I'm just truly looking forward to slowing down," she told the outlet.
Just a few days after the pair were photographed spending New Year's Eve in Anguilla, they .
"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 actors said in a joint statement. "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.
"star officially from the actor in Los Angeles Superior Court two months after they announced their split. Her court papers cited irreconcilable differences, PEOPLE reported. She also requested to restore her last name from Pitt back to Aniston. The later that year on Oct. 2.
In a candid and wide-ranging interview with
, Aniston opened up about mourning her marriage, her reaction to the barrage of headlines surrounding Pitt's budding relationship with Jolie and her desire for everyone to just "move on" already."There are many stages of grief," Aniston 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."
At one point, she shared her reaction to the of Pitt and Jolie, who had been denying romance rumors up until then, on vacation together in Kenya.
"I can't say it was one of the highlights of my year," she said. "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.' "
She continued, "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."
Two years following their high-profile split, the
actor told magazine that he and Aniston were still close. "Jen and I still maintain a deep friendship and have a lot of life together that isn't erased in any way," he said.Speaking about their split, he added, "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."
Six years after their split, Pitt about his marriage to Aniston — and swiftly walked back his comments, which he felt were misinterpreted. "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 told the outlet.
Fans interpreted the statement to mean that the actor found his life with Aniston uninteresting, which he was quick to correct.
"It grieves me that this was interpreted this way.
Jen is an incredibly giving, loving and hilarious woman who remains my friend. It is an important relationship I value greatly. The point I was trying to make is not that Jen was dull, but that I was becoming dull to myself — and that, I am responsible for," he said .Pitt and Jolie, who got engaged in 2012, at their 35-room winegrowing estate Château Miraval in Correns, France.
Aniston also moved on after Pitt, getting to actor in August 2012.
Three years later, the couple wed in a surprise ceremony in front of 70 loved ones at their shared home in Bel Air, California."Guests were told it was a ," a source told PEOPLE. "Jen and Justin wanted to surprise guests and guests were certainly surprised."
Initiating what would go on to become one of Hollywood's most high-profile (and ongoing) , Jolie cited irreconcilable differences from Pitt. She requested physical custody of the — Maddox, Pax, Zahara, Shiloh, Vivienne and Knox — and visitation rights for Pitt.
In a , Pitt said, "I am very saddened by this, but what matters most now is the well-being of our kids. I kindly ask the press to give them the space they deserve during this challenging time."
