Jennifer Aniston and Brad Pitt were once Hollywood’s golden couple. Both were actors and at the top of their game, as she was America’s Sweetheart as Rachel on Friends, while Brad was an A-list movie star. And they looked so gorgeous together. When they split in 2005, it felt as if a fairytale had come to a tragic end, but today, they’re close “buddies.”

The pair were first introduced in 1994 by their managers, but Jennifer was in a relationship. “[Pitt] was just this sweet guy from Missouri, you know? A normal guy,” she told Rolling Stone about the hunk in 2001.

By 1998, the stars had aligned, and they were both single. In such a Hollywood way, the couple were set up on their first date by their agents. They tried to date on the down-low by having dinners at each other’s houses, but eventually, word got out that two of the hottest people in Tinseltown were a couple. Brad and Jen made things official when he accompanied her to the Emmy Awards in September 1999.

The pair married in a star-studded wedding overlooking the ocean in Malibu on July 29, 2000. It featured a gospel choir, fireworks and plenty of famous guests, including Jen’s Friends costars Courteney Cox and Matthew Perry, as well as Cameron Diaz, Salma Hayek and Edward Norton.

It seemed like the two were in it forever, when in the same 2001 Rolling Stone interview, Jen revealed, “You know if there’s ever an argument, it’s not like you can go, ‘Screw you, I’m outta here!’ You’re there for the long haul. It’s a beautiful thing to actually realize that for the first time, to have that knowing. It takes the heat and the weight out of things.”

While to the rest of the world, the marriage seemed so solid, in 2004, Brad began falling for his Mr. and Mrs. Smith costar Angelina Jolie. Brad and Jen stunned fans when they announced on January 7, 2005, that they were separating. It came as such a shock, considering less than a week prior, they were photographed with their arms around each other during a romantic New Year’s vacation to Anguilla.

Jennifer filed for divorce on March 25, 2005, and less than a month later, the “Brangelina” rumors became more than just speculation. They were photographed together on a beach in Kenya, with Brad doting on Angelina’s then-3-year-old son Maddox. He went on to adopt the little boy as well as Angelina’s daughter Zahara, whom she adopted from Ethiopia in July 2005. The couple welcomed their first biological child, daughter Shiloh, in May 2006. The pair later added three more kids to their brood, for a total of six children.

The pair hurt Jen deeply when they posed for a steamy 60-page spread in the July 2005 issue of W magazine called Domestic Bliss: Angelina Jolie and Brad Pitt at Home. Two months later in her first post-split interview, Jennifer revealed, “I know Brad. Brad would say, ‘That’s art!’ There’s a sensitivity chip that’s missing,” about how painful the spread was for her. Their divorce was finalized in October 2005.

Brad seemed to diss his marriage to Jennifer in a 2011 interview with Parade. “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.”

After nearly 10 years together, Brad and Angelina married on August 23, 2014, at their chateau in France. But their wedded bliss came to a crashing end when the Maleficent star filed for divorce in September 2016, following a fight aboard their plane en route back to the U.S. from France. It was after the breakdown of Brad’s marriage to Angelina and their bitter divorce and child custody battle that Brad and Jennifer reunited together as friends.

Brad attended Jennifer’s star-studded 50th birthday party in February 2019. They sweetly crossed paths backstage at the 2020 Screen Actors Guild Awards, and fans went wild over the photo of the exes looking so happy to see each other.

Fans again lost it when the pair seemed to flirt with each other during a live table read via zoom for Fast Times at Ridgemont High in September 2020. As soon as Brad logged in, he smiled and asked Jennifer how she was doing, and The Morning Show star sweetly responded, “I’m doing good, baby, how about you?”

“It was absolutely fun. Brad and I are buddies, we’re friends,” Jennifer later revealed on SiriusXM’s The Howard Stern Show, adding, “And we speak, and there’s no oddness at all, except for everyone that probably watched it and was wanting there to be, or assumed there to be.”

Scroll down for a complete timeline of Brad Pitt and Jennifer Aniston’s relationship. 

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