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    • 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.
    • A Casual Meeting
    • The First Date
    • September 12, 1999: Red Carpet Debut
    • November 29, 1999: Rocking An Engagement Ring
    • July 29, 2000: The Wedding of The Year
    • November 22, 2001: Guest Starring on Friends
    • February 1, 2003: Is He The Love of Her Life?
    • February 2004: Baby Fever
    • May 2004: Mr. and Mrs. Smith
    • January 7, 2005: An Unfortunate Separation

    Unlike their romance, their first meeting was quite casual. The pair met sometime in 1994 via their managers, who happened to be friends. "He was just this sweet guy from Missouri, you know?” Jen told Rolling Stonein 2001. “A normal guy.”

    Their relationship wouldn't turn romantic until their first date four years later. Brad had just broken up with actress Gwyneth Paltrow and Jennifer called it quits with actor Tate Donovan, prompting their managers to set up a date. In 2004, Jen later told Diane Sawyerthat the "evening was really easy" and the date "was really fun."

    The sparks were ever so present on their first date so the couple dove right into a relationship. They walked the red carpet together for the first time at the 51st Primetime Emmy Awards, confirming relationship rumors in the process.

    While attending a Sting concert together on November 29, 1999, the Hollywood stars took the stage to show off Jennifer's new accessory: an engagement ring! The actor reportedly spent $500,000 on the custom bauble, which boasted plenty of diamonds set in a unique circular shape.

    The biggest celebrity wedding of 2000 was undoubtedly Brad and Jen's summer nuptials. The couple wed on a bluff overlooking the Pacific Ocean in Malibu in front of 200 guests. Brad wanted the private estate venue to look like a Zen garden so he ordered 50,000 roses, wisteria, tulips, and lotus flowers. A flawless bride, Jen wore a glass-beaded, low...

    The couple acted alongside each other in 2001 when Brad made a guest appearance on Jen's hit sitcom Friends. The episode, called "The One With The Rumor,"aired on November 22, 2001, and Brad's character actually hated Rachel Green, who was famously played by his wife.

    When asked if Brad was the love her life during Jennifer's cover interview for W Magazinein 2003 she responded with, "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.’ He’s certainly a big love in my life," she told t...

    With the end of Jennifer's time on Friends looming, the actress told The Guardian she was ready to have a babywith her husband of nearly four years. "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. So I'm just truly looking forward to slowing down," she said at the time.

    Despite Jen's baby fever three months prior, by May 2004 cheating rumors between Brad and his Mr. and Mrs. Smith costar Angelina Jolie began to swirl. In 2006, Jolie recounted to Vogue how she and Brad began to fall in love on-set of the film, saying, “Because of the film, we ended up being brought together to do all these crazy things, and I think...

    After a nearly five-year marriage and seven-year relationship, Brad and Jennifer announced their split to People on January 24, 2005. The statement read: “We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the...

    • Maggie Kreienberg
  1. Mar 17, 2024 · Jennifer Aniston and Brad Pitt first met in 1994 and began dating in 1998. Aniston and Pitt made their red carpet debut as a couple at the 1999 Emmy Awards. They got married at a...

    • 3 min
    • Sophie Dodd
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  2. 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...

    • 2 min
    • Jessica Vacco-Bolaños
  3. Feb 11, 2020 · February 11, 2020. Kevin Mazur/Getty Images. For over 20 years, America’s had a full-on obsession with Brad Pitt and Jennifer Aniston ’s relationship—from their status as America’s golden...

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  5. Jun 24, 2021 · CNN —. Jennifer Aniston and Brad Pitt really are all good, y’all. The pair were married from 2000 to 2005 and there is continued fascination with their relationship. Aniston recently...

  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...

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