Brad Pitt and Jennifer Aniston Relationship Timeline

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.”

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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.

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