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.

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  • Jennifer Aniston and Brad Pitt were married between 2000 and 2005
  • Brad infamously married his ‘Mr. & Mrs. Smith’ co-star, Angelina Jolie
  • Both Jennifer and Brad have remarried and divorced since their relationship ended
  • They appear to be friendly with each other, but have not reconciled romantically

Jennifer Aniston, 54, and Brad Pitt, 59, are one of Hollywood’s most iconic past couples. Jen, whose new movie, Murder Mystery 2, debuts on March 31, and Brad were the “It” couple in the early 2000s — or so fans thought. Unfortunately, their marriage ended after three years when Brad fell head-over-heels for his Mr. & Mrs. Smith co-star, Angelina Jolie. Following Brad’s 2016 divorce from Angelina and Jen’s split from Justin Theroux, the duo are seemingly on good terms. And after a brief reunion at the 2020 SAG Awards, everyone wanted 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

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Brad Pitt and Jen Aniston were together for six years in total between the late ’90s and early 2000s (Photo: Shutterstock)

Brad and Jen first met in 1994, when the actor was just a “normal guy”, according to Jen in a 2001 chat with Rolling Stone. “[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, which was 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. “It was weird,” she recalled. “That was a really easy evening. It was really fun.”

They 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 in November of that year and showed off the Friends star’s massive diamond ring on stage at New York City’s Beacon Theater.

Brad & Jen Wed In 2000

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

Brad Guest Stars On ‘Friends’

Brad Pitt appeared on ‘Friends’ during its eighth season in 2011 (Photo: Everett Collection)

If you were a Friends fan in the early 2000s, chances are you will recall Brad’s iconic guest appearance. He portrayed Rachel Green’s old classmate in the Season 8 episode titled, “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.

Brad And Jen Break Up In 2005

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Unfortunatry, Brad and Jen ended their marriage after five years together (Photo: Shutterstock)

Brad starred in the 2005 film Mr. and Mrs. Smith with his future wife Angelina, and rumors swirled that he had cheated on Jen with his co-star. 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 at the time. “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. For instance, Jennifer famously described her ex as “missing a sensitivity chip” in an interview with Vanity Fair. 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” from the paparazzi circus, per Reuters. “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,” he told Parade.

Brad & Jen Famously Reunite In 2020

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Brad Pitt’s and Jen Aniston’s famous reunion had fans wondering if they’de reconnect romantically (Photo: Shutterstock)

Almost 20 years after the pair wed, they reunited at Jen’s 50th birthday party at the Sunset Tower Hotel in Los Angeles in 2019. Unsurprisingly, this sparked reconciliation rumors. “Someone extended the invitation to Brad to come to Jen’s party and he accepted,” a source told E! News at the time. “He wanted to support Jen and it was a momentous occasion. But that’s the extent of it. It was a social evening with a lot of people who have been a part of her life. They definitely aren’t dating or on that path. They are friendly, but that’s it.”

The following year, they were seen congratulating each other backstage at the 2020 SAG Awards on Jan. 19, 2020. “They both embraced in a big long hug. They exchanged pleasantries and were visibly excited for each other,” an eyewitness shared EXCLUSIVELY with HollywoodLife. “The energy they both were showing each other was as electric as possible. You can tell their is a massive respect there. They didn’t stay long as they were whisked away back towards the showroom and they both signed a SAG Awards sign that all the winners have signed.”

The encounter went viral and had folks hoping they may fund their way back to one another. However, nothing more has happened between the former lovers, showing that they may stay friends for the long-run.

Are They Seeing Anyone Now?

Jen seems to be single as of March 2023. Brad, however, has been dating Paul Wesley‘s ex-wife, fitness enthusiast Ines de Ramon, since Nov. 2022. They have been spotted enjoying quality time together all over the world, such as when they celebrated New Year’s in Mexico and enjoyed a romantic dinner in Paris.