Brad Pitt and Jennifer Aniston's Relationship Timeline: Amicable Exes

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Brad Pitt Wearing a Tux With Jennifer Aniston

1994

Brad and Jen met for the first time because their managers were friendly. “[Brad] was just this sweet guy from Missouri, you know? A normal guy,” she told Rolling Stone later on in 2011.

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Jennifer Aniston With Long Hair and Brad Pitt

1998

Brad and Jen were set up by their agents — so Hollywood, right? “It was weird … That was a really easy evening. It was really fun,” she later told Diane Sawyer about their first date.

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Brad Pitt Wearing a Hat With Jennifer Aniston

1998

They tried to keep their relationship on the DL, but they were spotted kissing at a concert in Washington D.C. “We just wanted to keep it special. Keep it ours,” he later told Rolling Stone.

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Jennifer Aniston Wearing Brown With Brad Pitt in Sunglasses

September 1999

The duo made their public debut at the 51st Primetime Emmy Awards.

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Brad Pitt Wearing a Black Suit With Jennifer Aniston in a Black Outfit

November 1999

The California native showed off her new bling — a.k.a. her engagement ring — at a Sting concert in New York City.

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Jennifer Aniston in a Black Dress With Brad Pitt

July 2000

Brad and Jen got married in Malibu — and it cost a whopping 1 million dollars, NBD. The lavish affair included 200 guests, 50,000 flowers, a firework show and a gospel choir.

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September 2000

The newlyweds looked dapper at the Emmy Awards.

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Brad Pitt Wearing a Jacket With Jennifer Aniston in White

September 2001

Jen admitted her friends thought Brad was a “conceited f—k” at first, but later came around. Additionally, she gushed about her love. “You know, if there’s ever an argument, it’s not like you can go, ‘Screw you, I’m outta here!’” she said. “You’re there for the long haul. It’s a beautiful thing to actually realize that for the first time, to have that knowing. It takes the heat and the weight out of things.”

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Jennifer Aniston With Brad Pitt on Friends

November 2001

Brad and Jen starred alongside one another on Friends where Brad’s character was the president of the “I Hate Rachel Green Club.”

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Brad Pitt and Jennifer Aniston at the Globes Wearing Black

January 2002

Matching! The couple wore black outfits to the Golden Globes.

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Jennifer Aniston Giving a Loving Look to Brad Pitt

2003

Jennifer gave an interesting answer when an interviewer asked her if Brad was the love of her life. “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,’” she told W magazine at the time. “He’s certainly a big love in my life … 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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Jennifer Aniston Wearing a Black Dress With Brad Pitt

February 2004

After Friends ended, Jen alluded to having kids with Brad. “Yeah. 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 told The Guardian. “So, I’m just truly looking forward to slowing down.”

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May 2004

Brad and Angelina met on the set of Mr. and Mrs. Smith and sparks flew. Angelina later told The New York Times they “fell in love” during filming.

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Brad Pitt Wearing a Tux With Jennifer Aniston in White

January 2005

The couple took their last vacation together — where they were spotted kissing on the beach — but unfortunately, they announced their split in a joint statement shortly after their getaway. “We would like to announce that after seven years together we have decided to formally separate,” they said. “For those who follow these sorts of things, we would like to explain that our separation is not the result of any speculation reported by the tabloid media. This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another.”

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September 2005

Jen spoke out for the first time following their split. “Brad is not mean-spirited; he would never intentionally try to rub something in my face,” she told Vanity Fair. “In hindsight, I can see him going, ‘Oh — I can see that that was inconsiderate.’ But I know Brad. Brad would say, ‘That’s art!’ There’s a sensitivity chip that’s missing.”

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October 2005

#Brannifer no more! Their divorce is finalized.

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December 2008

Jen talked about Brad and Angelina’s romance and admitted she was upset about their relationship, naturally. “There was stuff printed there that was definitely from a time when I was unaware that it was happening,” she told Vogue. “I felt those details were a little inappropriate to discuss. That stuff about how she couldn’t wait to get to work every day? That was really uncool.”

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Brad Pitt Wearing a Tuxedo With Angelina Jolie

September 2014

Brad and Angelina finally got married in France.

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Justin Theroux Wearing a Suit With Jennifer Aniston

August 2015

Jennifer married Justin Theroux after they were first seen together in 2011.

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September 2016

Angelina filed for divorce from Brad.

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Brad Pitt With Long Hair With Jennifer Aniston

2017

Following his divorce, a source told Us Weekly he had “been texting” with Jennifer. “Brad told her he’s having a hard time with his split and they exchanged a few texts reminiscing about the past,” the insider shared.

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Jennifer Aniston Wearing a Flower Dress With Justin Theroux

February 2018

Justin and Jennifer announced their separation. “This decision was mutual and lovingly made at the end of last year,” their statement read. “We are two best friends who have decided to part ways as a couple but look forward to continuing our cherished friendship. Above all, we are determined to maintain the deep respect and love that we have for one another.”

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Jennifer Aniston Wearing a Sparkle Black Dress

December 2018

Jen spoke out about her previous marriages and revealed she’s happy. “I don’t feel a void. I really don’t. My marriages, they’ve been very successful, in [my] personal opinion,” she Elle. “And when they came to an end, it was a choice that was made because we chose to be happy and sometimes happiness didn’t exist within that arrangement anymore.”

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