The Jennifer Aniston and Brad Pitt Relationship Timeline

When history looks back at some of the greatest Hollywood love stories of all time, a few names are likely to be mentioned. We will never forget the romance between Brad Pitt and Jennifer Aniston that began in 1999 and lasted just six short years. During that time, the two were seen almost everywhere together. It was very sad when the couple eventually went their separate ways and found other partners/spouses.

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The iconic romance between the rugged mega-movie star and the adored star of the NBC sitcom Friends (how many actors have a hair style named after a character they played?) was such a beautiful display of love, and it was heartbreaking when it ended. And 15 years later, there are still many hopeful holdouts that Aniston and Pitt will someday reunite. As luck would have it, each of them separated from their respective partners, and both are now playing the field, so who’s to say if that field might lead to another romance between two of the most gorgeous celebs?

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Let’s look back at a celebrity romance for the ages and the events that could lead to what would be a very popular reunion.

Aniston and Pitt first crossed paths in 1994, their respective managers being friends. As she told Rolling Stone in 2001, “He was just this sweet guy from Missouri, you know? A normal guy.” It wasn’t until 1998 when their agents set them up on their actual first date when things started to heat up. They hit it off but tried to keep the relationship under wraps until they made their very first public appearance together at the Emmys on September 12, 1999. The world went absolutely bonkers!

In February 2001, Aniston supported hubby Pitt by attending the Los Angeles premiere for his film, The Mexican. He would return the favor in January 2002, when Aniston’s film The Good Girl premiered at the Sundance Film Festival. Rumors were already swirling that Aniston was pregnant with Pitt’s baby, but they were quickly debunked. Either way, the two looked very happy at all of their official appearances.

When Pitt was cast to star in the action movie Mr. & Mrs. Smith, he was originally slated to star opposite Nicole Kidman. Looking back, it not only would have been a very different movie, but it also would have changed history. Others originally in talks to star in the movie included Catherine Zeta-Jones, Gwen Stefani, Johnny Depp and Will Smith. The filmmakers decided to pair Pitt with Angelina Jolie, a move that would change history. While shooting the movie, the two began to fall in love, despite Pitt still being married to Aniston. Jolie had gone through her recent divorce from actor Billy Bob Thornton, the two of them having adopted seven-month-old Maddox in 2002. Even so, it wouldn’t be until spring 2005 when the relationship between Pitt and Jolie, quickly dubbed “Brangelina,” was official. The new power couple was caught on camera in Kenya in what W Magazine dubbed “Domestic Bliss.”

In January 2005, Pitt and Aniston decided to separate with their divorce finalized many months later on October 2. In September 2005, Aniston had an infamous interview with Vanity Fair dubbed “The Unsinkable Jennifer Aniston,” where she denied the accusations that her not wanting to have children caused the split. “That really pissed me off,” she told the publication. “I’ve never in my life said I didn’t want to have children. I did and I do and I will! The women that inspire me are the ones who have careers and children; why would I want to limit myself? I’ve always wanted to have children, and I would never give up that experience for a career. I want to have it all.”

In 2008, Aniston had a high-profile interview with Vogue and addressed something Jolie said to People Magazine two years earlier. In a feature cheekily called, “Angelina: How Brad Pitt & I Fell in Love,” Jolie revealed what many wanted to know. “Because of the film, we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened. I think a few months in I realized, ‘God, I can’t wait to get to work.’ Anything we had to do with each other, we just found a lot of joy in it together and a lot of real teamwork. We just became kind of a pair.” Even so, the relationship didn’t start right away, and they remained “very, very good friends” until the Pitt-Aniston separation. Aniston responded — when asked by Vogue about the Jolie interview, — that “there was stuff printed there that was definitely from a time when I was unaware that it was happening. I felt those details were a little inappropriate to discuss ... That stuff about how she couldn’t wait to get to work every day? That was really uncool.”

The Pitt-Jolie relationship would last almost twice as long as his romance with Aniston. “When someone asked me why Angie and I don’t get married, I replied, ‘Maybe we’ll get married when it’s legal for everyone else,’” Pitt told Parade in a controversial 2009 cover story. “I believe everyone should have the same rights,” he continued. “They say gay marriage ruins families and hurts kids. Well, I’ve had the privilege of seeing my gay friends being parents and watching their kids grow up in a loving environment.”

Even so, Pitt and Jolie were engaged in April 2012 and got married in September 2014. That would turn out to be the beginning of the end.

Pitt stirred things up in 2011 when he addressed his failed marriage to Aniston telling Parade (again), “It became very clear to me that I was intent on trying to find a movie about an interesting life, but I wasn’t living an interesting life myself. I think that my marriage to Aniston had something to do with it. Trying to pretend the marriage was something that it wasn’t.”

People immediately presumed Pitt was calling Aniston “uninteresting,” so the actor clarified his earlier statement with another one, “It grieves me that this was interpreted this way. Jen is an incredibly giving, loving and hilarious woman who remains my friend. It is an important relationship I value greatly. The point I was trying to make is not that Jen was dull, but that I was becoming dull to myself — and that, I am responsible for.”

Aniston eventually met actor and filmmaker Justin Theroux in 2007, although they didn’t get involved romantically until May of 2011. They were married on August 5, 2015 after a three-year engagement but ultimately separated at the end of 2017 and divorced in 2018.

As Aniston’s new marriage was still in its infancy, things seemed to be coming to a head four years after Pitt and Jolie finally tied the knot. Jolie filed for divorce from Pitt in September 2016 citing “irreconcilable differences.” In February 2019, Pitt attended Aniston’s 50^th birthday bash, and the public discussed the possibility that the ‘90s power couple might finally be reconciling.

During the 2020 awards season, Pitt was honored by various groups for his performances in Quentin Tarantino’s Once Upon A Time in Hollywood. On the red carpet at the Golden Globes in early January 2020, Pitt was asked about Aniston, and he called her “a good friend.” After the ceremony, they attended some of the same parties.

On January 24, 2020, both Pitt and Aniston appeared at the Screen Actors Guild Awards, Pitt nominated for Once Upon a Time in Hollywoodand Aniston for her Apple+ series,The Morning Show. They both won their respective categories and Pitt was spotted watching with pride from offstage as Aniston made her own acceptance speech, and he even grabbed her hand as she came offstage. The fans were excited about a possible reunion, but when asked about it, Pitt was quoted as saying, “I don’t know, I’m blissfully naïve, and I’m gonna stay that way.”