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  1. Aug 11, 2022 · From their 1994 meeting to their 2020 reunion, here is everything you need to know about the iconic couple's romance. See their milestones, from their engagement and wedding to their divorces and friendships.

    • Maggie Kreienberg
    • 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.
  2. Mar 17, 2024 · A timeline of the former couple's romance, from their 1994 meeting to their 2020 reunion. See photos, quotes and milestones of their marriage, divorce and friendship.

    • Sophie Dodd
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  3. May 17, 2022 · It's been close to two decades since Jennifer Aniston and Brad Pitt ended their marriage, and while some fans are still holding out hope the two will reconnect romantically, a source tells...

  4. Feb 11, 2020 · A complete timeline of Brad Pitt and Jennifer Aniston's relationship from when they met to their recent friendship.

  5. Aug 16, 2023 · How did the former couple, who split in 2005, become buddies and respectful of each other? See their quotes and photos from over the years.

  6. Feb 1, 2023 · Brad Pitt and Jennifer Aniston had one of the most buzzed-about relationships in Hollywood history. From their '90s dates (the matching looks!) to their five-year marriage and eventual split,...