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  2. Feb 15, 2017 · Getty Images. An article in Vanity Fair revealed that Jen Aniston had hoped to be pregnant during the same window of time she found herself divorcing Brad Pitt. According to an unnamed...

    • 10 min
    • 1994. The two cross paths for the first time, and Hollywood is forever changed. In an interview with Rolling Stone, Aniston says they first met back in 1994 since their managers were friends.
    • 1998. Pitt and Aniston go on their first date after being set up by their agents—a true Hollywood romance, right? They try to keep things quiet for as long as they can, but this proves difficult since Pitt is one of the biggest movie stars in the world and Aniston is America's sweetheart.
    • September 12, 1999. Pitt and Aniston make their public debut as a couple on the red carpet for the Emmy Awards in 1999—forever immortalizing Brad's sunglasses.
    • November 21, 1999. Just a few months after that initial debut, Pitt and Aniston crash the stage of a Sting concert (ha ha ha ha) in New York City and flaunt their engagement.
  3. May 17, 2022 · The former couple divorced in 2019. Aniston, meanwhile, tied the knot to Justin Theroux in 2015. They split two years later but also remain friends. Last June, Aniston spoke to People about...

    • 2 min
    • Jessica Vacco-Bolaños
  4. Mar 17, 2024 · March 25, 2005: Jennifer Aniston files for divorce from Brad Pitt . The Break-Up star officially filed for divorce from the actor in Los Angeles Superior Court two months after they...

    • 3 min
    • Sophie Dodd
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  5. Feb 19, 2024 · When they walked down the aisle, Jennifer Aniston and Brad Pitt didn't bother to sign a prenuptial agreement. This would have allowed Aniston to cash in bigtime in the event of a divorce, but instead, she walked away with the residence she and Pitt had purchased together.

  6. Jul 24, 2023 · Aniston and Pitt's split took place shortly after rumors popped up that the actor had been getting close to his "Mr. and Mrs. Smith" co-star Angelina Jolie. Just months after Aniston filed for divorce, Pitt and Jolie came out as a couple in a W Magazine spread (via Glamour ).

  7. Feb 16, 2019 · Brad Pitt reportedly has second thoughts about the way he dealt with his divorce from Jennifer Aniston, whom he was married to from 2000 to 2005. A source told Us Weekly that Pitt "of...

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