Jennifer Aniston and Brad Pitt’s relationship has fascinated people for decades. From his sunrise guest appearance on Friends to their viral reunion in 2020, people all over the world have kept up with the couple through it all. This is why we have decided to make a comprehensive list of everything that has happened between the two, including first dates, marriages, divorces and more. Keep reading for more.
1994: Jennifer Aniston and Brad Pitt first meet
At some point in 1994, Aniston and Pitt met after their managers introduced them.
Says Aniston of their first meeting, “He was just this sweet guy from Missouri. He was a normal guy.” The two didn’t start dating then, though, and instead remained friends.
Fun fact: 1994 was also the first year that Friends was on the air, so it was a big year for Aniston.
1998: Jennifer Aniston and Brad Pitt begin dating
Four years after their initial meeting, the two actors decided to go on their first official date at some point in 1998. This was pretty quickly after Pitt ended his engagement to Gwyneth Paltrow.
“That was a really easy evening,” Aniston said of their first date, also noting that they immediately knew they were meant to be.
September 12, 1999: The couple makes their red carpet debut
During the 1999 Emmy Awards, Aniston and Pitt made their red carpet debut. That year, her hit show Friends was nominated in the Outstanding Comedy Series category, while co-star Lisa Kudrow was also nominated that year in the Outstanding Supporting Actress in a Comedy Series category. Sadly, both lost.
November 21, 1999: Jennifer Aniston and Brad Pitt get engaged
After taking the stage at a Sting concert, Aniston announced her engagement to Pitt. She then showed off her engagement ring, which her fiancé reportedly spent seven months designing. How romantic is that!
July 29, 2000: The duo ties the knot
Not even a year after announcing their engagement, Aniston and Pitt tied the knot in front of 200 of their closest friends and family in Malibu, California. The wedding reportedly cost about $1 million.
Many of Aniston’s Friends co-stars were in attendance to celebrate the special occasion, but unlike when Courteney Cox got married, Aniston never got a shoutout on the show.
September 10, 2000: The married couple walks the red carpet
Later in 2000, Aniston and Pitt walked their first-ever red carpet as a married couple at the Emmy Awards. That year, Friends was nominated in the Outstanding Comedy Series category. Aniston and Kudrow were also nominated in the Outstanding Supporting Actress in a Comedy Series category. Similar to the 1999 Emmys, though, the show lost.
November 1, 2001: The couple creates an entertainment company
Wanting to do more than act, Aniston and Pitt formed a production company called Plan B Entertainment in 2001 alongside Brad Grey and Kristin Hahn.
Explained Aniston, “We started this little company underground, but we didn’t really talk about it because we didn’t want to be accused of being actors who have vanity deals where you don’t do anything.”
Plan B Entertainment did go on to produce things like Troy (2004) and Charlie and the Chocolate Factory (2005), but after Pitt and Aniston divorced, Grey became the sole owner of it.
November 22, 2001: Brad Pitt visits Central Perk
November 22, 2001, will live in television infamy because it was the day Pitt guest starred on Friends alongside Aniston. He played Will Colbert, a high school friend of Ross’ and co-creator of the “I Hate Rachel Green club.”
Said Pitt, “It was a great cast. But I flubbed my first line. We had to stop and start again.” The actor went on to earn an Emmy nomination for his work on Friends.
February 1, 2003: Jennifer Aniston begins to question the relationship
While speaking with W in 2003, Aniston told the magazine that she wasn’t sure if Pitt was the love of her life.
“He’s certainly a big love in my life, and I know that we have something special, especially in all this chaos,” the actress said, “[but] I’ve never been someone who says, ‘He’s the love of my life.’”
Pitt never responded to this article.
February 22, 2004: Jennifer Aniston reveals she is ready to start a family
Aniston might not know if Pitt is the love of her life, but in 2004 she did say she was ready to start a family with him.
“It’s time. You know, I think you can work with a baby, I think you can work pregnant, I think you can do all of it,” the actress said. “So I’m just truly looking forward to slowing down.”
This was also around the same time her hit show Friends was coming to a close.
January 7, 2005: Jennifer Aniston and Brad Pitt officially separate
A little less than a year after admitting that they were trying to have a baby, the couple released a joint statement detailing that they would be formally separating.
“After seven years together, we have decided to formally separate. 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,” the pair said.
“We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months.”
March 24, 2004: Jennifer Aniston files for divorce
A few months after announcing their separation, Aniston officially filed for divorce. The reason for the divorce still remains a mystery, but after it was finalized on October 2, 2004, Aniston said that she loved “the discovery of what will be happening and just kind of sitting back and not knowing.”
October 10, 2006: Jennifer Aniston says she’s ‘not defined’ by that relationship
During their divorce, Pitt was actively seeing Angeline Jolie, who he met on the set of the 2003 film Mr. & Mrs. Smith.
Aniston commented on this relationship in 2006, saying, “What happened to him after the separation—it’s his life now. I’ve made a conscious effort not to add to the toxicity of this situation. I haven’t retaliated. I don’t want to be a part of it.”
She then went on to say that she just wants everyone to “move on.”
“I am not defined by this relationship. I am not defined by the part they’re making me play in the triangle. It’s maddening to me.”
September 15, 2011: Brad Pitt comments on the relationship
Seven years after their divorce, Pitt sat down with Parade and explained how he didn’t find life interesting when he was with Aniston.
“I spent the ‘90s trying to hide out, trying to duck the full celebrity cacophony. I started to get sick of myself sitting on a couch, holding a joint, hiding out. It started feeling pathetic. 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,” the actor said.
“I think that my marriage [to Jennifer Aniston] had something to do with it. Trying to pretend the marriage was something that it wasn’t.”
Aniston never commented on how this statement made her feel.
February 9, 2019: Brad Pitt celebrates Jennifer Aniston’s birthday
It turns out there is no one else Aniston would rather celebrate her 50th birthday with than her ex-husband! Pitt was invited to the actress’ 50th birthday party, but it is unclear exactly what happened between the two while he was there.
January 19, 2020: Jennifer Aniston and Brad Pitt reunite once again
At the 2020 Screen Actors Guild (SAG) Awards, Aniston and Pitt reunited, and it caused the whole internet to go crazy. The two were seen hugging and smiling off the red carpet and even sparked some romance rumors online, but those turned out to be false.
September 18, 2020: Jennifer Aniston and Brad Pitt film a table read
During the COVID-19 pandemic, Pitt and Aniston appeared virtually together for the Dane Cook Presents Feelin’ A-Live: Fast Times at Ridgemont High table read alongside Ray Liotta, John Legend, Matthew McConaughey, Julia Roberts, Morgan Freeman, Jimmy Kimmel and Henry Golding. The reading was done to raise money for REFORM Alliance and Sean Penn’s nonprofit CORE (Community Organized Relief Effort).
June 23, 2021: Jennifer Aniston comments on her current relationship status
Despite being divorced for some time, Aniston simply cannot escape her relationship with Pitt. While appearing on SiriusXM’s The Howard Stern Show, the actress said that she and Pitt “Are buddies, we’re friends.”
“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,”
She also commented on how the 2020 virtual reunion made her feel, saying, “We had fun, and it was for a great cause.”
November 9, 2022: Jennifer Aniston addresses rumors about her and Brad Pitt not having kids
Despite trying to have a family, Aniston and Pitt were never successful, with the actress revealing that she was “going through IVF, drinking Chinese teas, you name it. I was throwing everything at it. I would have given anything if someone had said to me, ‘Freeze your eggs. Do yourself a favor.’ You just don’t think about it.”
Aniston also addressed the rumors as to whether the two got divorced because she didn’t want to have kids.
“God forbid a woman is successful and doesn’t have a child. And the reason my husband left me, why we broke up and ended our marriage, was because I wouldn’t give him a kid. It was absolute lies,” the actress said.
