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A Timeline Of Jennifer Aniston And Brad Pitt's Relationship

Updated January 23, 2020 6.2k views21 items
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Although it's been more than 20 years since they first started dating, Brad Pitt and Jennifer Aniston still stand out as one of the most celebrated couples in Hollywood history. The stars were both gaining traction in their careers at the beginning of their relationship, and went ont to develop what appeared to be a movie-worthy romance. They started out as friends, then admitted to falling in love on their very first date. The beginning of their partnership was filled with long trips, romantic nights together, and plenty of love. 

Unfortunately, things weren't as perfect as they seemed. At what some would consider the height of their careers, Aniston and Pitt separated. A few months later, Pitt was happily dating his Mr. and Mrs. Smith co-star Angelina Jolie, leaving his ex-wife confused and brokenhearted. 

While Pitt and Aniston's relationship is one part of the most shocking love triangle in Hollywood history, dedicated fans still maintain hope that the pair will reunite someday. Who knows? They've reportedly been in contact since Pitt attended Aniston’s 50th birthday celebration in February 2019.

While there's no indication this couple is about to get back together, they're both currently single. Yet their long and fraught history can't just be erased. Before you root for this couple to get back together, take a look at a complete timeline of their relationship.

  • Photo: Meet Joe Black / Universal Pictures

    November 1998: They Show Up Separately To The 'Meet Joe Black' Premiere

    While their relationship was still fairly new, Pitt and Aniston desperately tried to evade the incessant questions from the media.

    During the premiere of Pitt's film Meet Joe Black in late 1998, the pair arrived seperately to maintain the privacy of their relationship. They also banned media from the after-show party, effectively keeping anyone from gaining a definitive answer on their relationship status. 

  • February 1999: Pitt Throws A Party For Aniston's 30th Birthday

    Despite their attempts to stay out of the public eye, the relationship between Aniston and Pitt flourished behind the scenes.

    In February 1999, Pitt threw a party for Aniston's 30th birthday at Sunset Boulevard's Barfly restaurant. He invited 500 of her friends to celebrate the big occasion. The pair was growing closer together, and Aniston's friends very much approved of her new relationship.

  • February 11, 1999: Pitt And Aniston Fly To Acapulco, Mexico, On A Private Jet

    After the massive birthday celebration in Los Angeles, Pitt and Aniston took things one step further. On Aniston's actual birthday, the pair boarded a private jet with nine close friends and flew to Acapulco, Mexico.

    The couple celebrated Aniston's birthday again, this time in an international location. They also stayed in Mexico for Valentine's Day, enjoying a romantic and fun evening together. 

  • Photo: Featureflash Photo Agency/Shutterstock.com

    September 1999: They Make Their Public Debut As A Couple At The Emmy Awards

    In September 1999, Pitt and Aniston finally decided to make their relationship public. They appeared together at the Shrine Auditorium in Los Angeles for the 1999 Emmy Awards.

    The actors each sported a tousled, very '90s look, and they seemed happy they were finally able to talk openly about their relationship.