Romance Timeline of Brad Pitt & ‘Friends’ Star Jennifer Aniston

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.

The ‘it’ couple of the 90s.

Brad and Jen first met in 1994, when the actor was just a “normal guy”. Years later 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!

Brad & Jen wed in 2000.

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, “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’.

He portrayed Rachel Green’s old classmate in the season eight episode, “The One With the Rumor,” which aired in 2001. 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 called 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. Brad addressed the breakup and said, “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. 

Almost 20 years after the pair wed, they reunited at Jen’s 50th birthday party. 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. “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.

They both adopted puppies together in 2021

Let’s be honest: this puppy thing could go either way. On one hand, it’s definitely the kind of activity Brad Pitt & Jennifer Aniston would engage in if they were dating. At the same time . . . Brad Pitt’s going through a lot right now. The dude just survived a brutal custody battle that might not be over yet. So wouldn’t it make sense that an old friend, someone like Jennifer Aniston, would try to help him feel better?

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