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Jennifer Aniston & Brad Pitt’s Romance Timeline: From Hollywood’s Golden Couple To Divorce To Friendship

Take a look back at former power couple Jennifer Aniston and Brad Pitt’s relationship, from their lavish wedding and subsequent split, to their eventual reunion.

Jennifer Aniston, 52, and Brad Pitt, 57, are one of Hollywood’s most iconic couples. The pair’s relationship has been quite a rollercoaster through the years, from marriage to divorce, nemeses to pals, these two have been through it all. Following Brad’s 2016 divorce from ex-wife Angelina Jolie and Jen’s split from Justin Theroux, the duo are seemingly on good terms, and everyone wants to know whether they’ll ever get back together. Take a look back at their love story, which has spanned more than a quarter of a century.

The ‘it’ couple of the 90s.

Brad and Jen first met in 1994, when the actor was just a “normal guy”. In an interview with Rolling Stone, Jen said their managers were friends. “[Pitt] was just this sweet guy from Missouri, you know? A normal guy,” she told the outlet. It would be four years until they went on their first date — set up by their agents, in true Hollywood fashion. Years later, during a 2004 interview with Diane Sawyer on ABC’s Primetime, Jen said that she knew she and Brad were meant to be on that first date, explaining, “It was weird … That was a really easy evening. It was really fun.” They eventually made things official when they stepped out on the red carpet together at the Emmy Awards in 1999, and got engaged just months later! They crashed a Sting concert, and appeared on stage in New York City to flash the Friends star’s massive diamond ring.

Brad & Jen wed in 2000.

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The couple’s wedding was among the biggest news stories at the turn of the century. They said their ‘I do’s on July 29 in the year 2000, in front of 200 guests, with a lot of lavish trimmings including 50,000 flowers, four bands, a gospel choir, and fireworks to end the night. Jennifer told Rolling Stone in 2001, “I had those typical jitters the day before my wedding, but the day of, I was just excited in a good way.”

Brad guest stars on ‘Friends’.

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If you were a Friends fan in the early 2000s, chances are you recall Brad’s iconic guest appearance. He portrayed Rachel Green’s old classmate in the season eight episode, “The One With the Rumor,” which aired in 2001. The filming took place the year after they got married and the episode became a memorable one due to their real-life romance making major headlines at the same time. In the 2021 Friends reunion, Jen revealed he was one of her favorite guest stars. The actress referred to her ex-husband as “Mr. Pitt” when bringing him up along with other talented actors such as Sean Penn and Ben Stiller.

The couple call it quits in 2005.

When Brad starred in Mr and Mrs Smith with future wife Angelina, rumors that he had cheated began to circulate. A few months after these initial reports, Brad and Jen sadly announced they were calling it quits. “We would like to announce that after seven years together we have decided to formally separate,” they wrote in a statement to People. “For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another.”

But in the years following their breakup, there seemed to be plenty of animosity between the pair. In an interview with Vanity FairJennifer famously described her ex as “missing a sensitivity chip”. She added, “Brad is not mean-spirited; he would never intentionally try to rub something in my face,” she said. Meanwhile, Brad addressed the breakup and the fact he “spent the ’90s trying to hide out.” He told 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.”

Brad & Jen eventually reunite (as friends) in 2020. 

brad jen

Almost 20 years after the pair wed, they reunited at Jen’s 50th birthday party at the Sunset Tower Hotel in Los Angeles. The following year they were seen chatting it up behind the scenes at the 2020 SAG Awards on January 19, 2020. “Brad was there first backstage finishing photos and saw Jen in the corner of his eye when she came to the back,” a HollywoodLife source dished EXCLUSIVELY on January 22. “He repeatedly called for her to come over and kept saying, ‘Aniston, Aniston.’ He never called her Jen. She heard him but didn’t respond and almost went to the other room to avoid the meetup.” The brief encounter quickly went viral, and did little to quell fans’ hope that the pair would one day reunite romantically.


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