It’s been two decades since Brad Pitt and Jennifer Aniston got married and subsequently divorced, but it all still feels like yesterday. Even when the World War Z actor tied the knot with Angelina Jolie and the Dumplin’ actress got hitched to Justin Theroux, fans still held out hope for the former couple.
That hope only increased when both stars separated from their respective partners in more recent years. “WHAT IF JENNIFER ANISTON AND BRAD PITT START DATING #dead,” one user tweeted in February 2018 shortly after the Friends alum and the Maniac star announced their separation, while another wrote, “Brad Pitt and Jennifer Aniston are getting back together. I called it first.”
A pal of Aniston’s exclusively told Us Weekly at the time that “Jen wouldn’t consider being with Brad in a romantic way,” but “there is always a spot in her heart for him.”
The Morning Show star spoke highly of both her former spouses later that year. “My marriages, they’ve been very successful, in [my] personal opinion,” she told Elle in a story published in December 2018. “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.”
Things all came to a head in February 2019, when the Oscar winner showed up at Aniston’s 50th birthday party. The former couple hugged it out after Pitt gifted her with a card, an onlooker told Us at the time, noting that they chatted for about 10 minutes before he went to hang out with a group of friends. Eleven months later, they reunited again at the 2020 SAG Awards.
What this means for the future of the pair remains to be seen, but you can still look back at their past now. Scroll down to revisit Pitt and Aniston’s relationship.
Hollywood's leading man and the sweetheart of television were set up by their agents in 1998. From the get-go, they felt like they had something special. "We both [knew] on our first date," Aniston told Diane Sawyer in a January 2004 interview. The actress said it was a "really easy evening ... really fun."
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The power couple iconically made their debut on red carpet for the 51st Primetime Emmy Awards. Aniston's series, Friends, was up for Outstanding Comedy Series at the time, but lost to Ally McBeal.
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The gorgeous couple crashed a Sting concert in New York City, where they proudly showed off Aniston's engagement ring.
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On July 29, 2000, Pitt and Aniston both said "I do" in a luxurious Malibu wedding.
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The newlyweds hit up the 52nd Primetime Emmy Awards, where Aniston was up for Outstanding Supporting Actress in a Comedy Series (Friends). She lost the prize to Megan Mullally (Will & Grace).
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Pitt made his first and only appearance on the actress' sitcom, Friends, on November 22, 2001, in an episode called "The One With the Rumor." His character, Will, hated Aniston's character, Rachel, in high school, so he (along with David Schwimmer's Ross) started a rumor that she was born with both male and female reproductive parts.
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The happy couple made their way to the 59th Golden Globe Awards, where Aniston was nominated for Best Supporting Actress - Series, Miniseries or Television Film and Friends was nominated for Best Television Series – Musical or Comedy. Neither took home their respective trophies.
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Though Aniston has been vocal in recent years about her plans to forego motherhood, she was whistling a different tune in 2004. "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 of starting a family with her then-husband. "So I'm just truly looking forward to slowing down."
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The Fight Club star met Angelina Jolie on the set of Mr. & Mrs. Smith.
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Aniston publicly addressed their decision to split. "He makes his choices. He can do — whatever," she told Vanity Fair. "We're divorced, and you can see why."
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The divorce was finalized.
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The By the Sea costars welcome their first biological child, Shiloh, on May 27, 2006. The couple also shares son Maddox, son Pax, daughter Zahara and twins Vivienne and Knox.
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After months of rumors that Pitt cheated with Jolie while filming their action movie — which the actor has denied over the years — he and Aniston announced their separation in a joint statement, noting that the decision was "not the result of any speculation reported by the tabloid media."
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Brangelina got married on August 23, 2014, in a private ceremony in France.
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The award-winning actress tied the knot with Justin Theroux at their estate on August 5, 2015.
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The Maleficent star filed for divorce from Pitt. (The two reached a custody agreement for their six children in late 2018.)
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More than a decade after their separation, Pitt and Aniston began texting each other, a source close to the Mother's Day star revealed to Us in March 2017. "They started talking once he wished her a happy birthday," the insider said at the time.
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The comedic actress and the Spy Who Dumped Me actor announced their split on February 15, 2018. "In an effort to reduce any further speculation, we have decided to announce our separation," their statement to Us Weekly read. "This decision was mutual and lovingly made at the end of last year. We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship."
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One nail in the coffin for Theroux was when he "stumbled upon old Post-it notes Brad had written," a source told Us. "Sweet little Post-its like, 'You looked nice tonight' or 'Miss you already.'"
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Aniston and Pitt reunited at her 50th birthday party.
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Aniston and Pitt made headlines in January 2020 after they reunited backstage at the SAG Awards. When Aniston won outstanding drama actress for her role in The Morning Show, a source told Us that the Once Upon a Time in Hollywood star “stopped” what he was doing to watch his ex-wife’s acceptance speech. “He was very into it. He wanted to hear what she had to say,” the source said. “He looked proud. When he walked away after her speech ended, it appeared he wiped his eye.”
Aniston, for her part, told reporters that Pitt watching her speech was “sweet.” The twosome were smiling from ear to ear in the photos from their embrace.
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After the exes’ SAG Awards reunion, a source exclusively told Us that while Aniston has “forgiven [Pitt] for his past mistakes and what he put her through,” she is “not interested in [him] in a romantic sense.” A second insider revealed that the movie stars “actually think it’s hysterical that fans are so obsessed with them getting back together.”
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