A Timeline Of Jennifer Aniston And Brad Pitt's Relationship

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.

  • 1994: The Couple First Meets - Just Casually, Though
    Photo: Bart Sherkow/Shutterstock.com

    1994: The Couple First Meets - Just Casually, Though

    Aniston and Pitt first met in 1994, though that wasn't the start of their romance. Their managers were friends, and that relationship brought the actors together.

    At the time, Aniston was dating actor Tate Donovan and Pitt was dating Gwyneth Paltrow. Although their first meeting was completely casual, Aniston described Pitt as a "sweet guy from Missouri," saying he was totally normal in her eyes.

  • 1998: The Couple Goes On A Date Set Up By Their Managers

    After their 1994 meeting, the pair didn't connect again until 1998. As they were originally introduced by their managers, it only makes sense that their managers would arrange their first official date.

    Aniston later said in an interview with Diane Sawyer that they both knew they were meant to be after that first romantic meeting. She described the evening as "easy" and "really fun," cementing the idea that Hollywood's new golden couple was a perfect match.

  • March 1998: Aniston Doesn't Return Pitt's Phone Call Before Leaving For Filming In England

    After their successful first date, Pitt waited the obligatory few days before calling Aniston. Aniston, for her part, was preparing to leave for England to film the season four finale of Friends. Pitt left a message suggesting they meet again and even offered to come over and help her pack, but Aniston was so nervous that she never called him back.

    The pair didn't see each other again until Aniston returned from across the pond - though Aniston later made it clear she'd been in love since their first meeting.

  • Late 1998: Pitt Visits The Set Of 'Office Space' To Spend Time With Aniston
    Photo: Office Space / 20th Century Fox

    Late 1998: Pitt Visits The Set Of 'Office Space' To Spend Time With Aniston

    After Aniston returned from England, her relationship with Pitt took off. When Aniston left for Texas to film Office Space, Pitt accompanied her on the journey. The two stayed together at the Four Seasons Hotel, separate from the rest of the cast. During the stay, Aniston's dog went missing and Pitt pitched in with the cast to help her find it. 

    Despite the fact everyone on set knew they were together, the pair was still trying to keep things private - and for good reason. Hollywood was already obsessed with their story, and PAs on the set of the movie were offered $50,000 to get a picture of the two of them together.