A Complete Timeline of Brad Pitt and Jennifer Aniston's Relationship

They've come a long way.

26th Annual Screen Actors Guild Awards - Media Center
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Jennifer Aniston and Brad Pitt have gone from film's hottest couple to husband and wife to nemeses to...great friends? It seems so: Pitt and Aniston have been seen more and more together in the years post-split. And now that Pitt and Aniston are both single once again, following Pitt's ongoing divorce from Angelina Jolie and Aniston's divorce from Justin Theroux, debating whether or not they will (or should) reunite has become a national pastime. In honor of The Great Debate, let's take a look back at their love story and the latest developments.

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The Mexican Premiere
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The two cross paths for the first time, and Hollywood is forever changed. In an interview with Rolling Stone, Aniston says they first met back in 1994 since their managers were friends. "[Pitt] was just this sweet guy from Missouri, you know? A normal guy," she said.

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Brad and Jen go on their first date after being set up by their agents—a true Hollywood romance, right? They try to keep things quiet for as long as they can, but this proves difficult since Brad is one of the biggest movie stars in the world and Jen is America's sweetheart. (Also, big ups to their beauty lewks in this photo.)

September 12, 1999
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Brad and Jen make their public debut as a couple on the red carpet for the Emmy Awards in 1999—forever immortalizing Brad's sunglasses.

November 21, 1999
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Just a few months after that initial debut, Brad and Jen crash the stage of a Sting concert (ha ha ha ha) in New York City and flaunt their engagement. In their defense, there was no Instagram back then.

July 29, 2000
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Brad and Jen tie the knot in a lavish Malibu wedding, which is naturally hounded by paparazzi—thus the aerial shots. Look at all those tents! The phrase "media circus" couldn't be more apt.

July 29, 2000
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There are literally fireworks the night of the wedding. It was that lavish.

September 10, 2000
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Brad and Jen make another appearance at the Emmy Awards, this time as newlyweds (and looking classy AF, we might add).

September 2001
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Jen talks about Brad in an interview with Rolling Stone. She admits that her friends worried Brad would be a "conceited f*ck" at first, but immediately came around because he's actually just the best person. She also talks marriage and being in it for the long haul.

To quote: "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."

November 2001
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Brad Pitt guest stars in Friends (specifically, "The One with the Rumor") where he wears a jaunty sweater and frosted tips and, oh yeah, hates Rachel Green. It's a major moment for people into his relationship with Jen, a.k.a. everyone.

January 20, 2002
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Brad and Jen attend the Golden Globes, where both she and Friends are nominated. Neither wins, but Jen and Brad matched outfits, so there's that.

February 2003
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When an interviewer for a W magazine profile refers to Brad as the love of Jen's life, her response is...interesting.

"Is he the love of my life? I think you’re always sort of wondering, 'Are you the love of my life?' I mean, I don’t know, I’ve never been someone who says, 'He’s the love of my life.' He’s certainly a big love in my life...And I know that we have something special, especially in all this chaos. In this nutty, brilliant, wonderful, hard business that we have, it’s nice to have somebody who’s anchored and knows you, really knows all of you."

January 2004

Jen tells Diane Sawyer that she and Brad both knew they were meant to be on their first date: "It was weird...That was a really easy evening. It was really fun."

February 2004
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In an interview with The Guardian, Jennifer talks about the end of Friends and her desire to start a family with Brad: "It's time. 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. So I'm just truly looking forward to slowing down."

May 2004
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Brad Pitt and Angelina Jolie meet on the set of Mr. and Mrs. Smith, and sparks fly/explode all over the place—specifically, all over Brad's marriage. Angelina later described falling for Brad while filming the movie during an interview with Vogue:

"Because of the film we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened. I think a few months in I realized, 'God, I can’t wait to get to work.' Whether it was shooting a scene or arguing about a scene or gun practice or dance class or doing stunts—anything we had to do with each other, we just found a lot of joy in it together and a lot of real teamwork. We just became kind of a pair. And it took until, really, the end of the shoot for us, I think, to realize that it might mean something more than we’d earlier allowed ourselves to believe. And both knowing that the reality of that was a big thing, something that was going to take a lot of serious consideration."

January 2005
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Brad and Jen officially split, offering the below joint statement:

"We would like to announce that 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. 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."

September 2005
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Jen addresses the split in an interview with Vanity Fair, and famously describes Brad as "missing a sensitivity chip" thanks to a W magazine spread featuring him and Angelina.

"Brad is not mean-spirited; he would never intentionally try to rub something in my face," she says. "In hindsight, I can see him going, 'Oh—I can see that that was inconsiderate.' But I know Brad. Brad would say, 'That’s art!' There’s a sensitivity chip that’s missing."

September 2005
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In that same interview with Vanity Fair, she also addressed the rumors of her not wanting to have children caused the split. “That really pissed me off,” she said to the magazine. “I’ve never in my life said I didn’t want to have children. I did and I do and I will! The women that inspire me are the ones who have careers and children; why would I want to limit myself? I’ve always wanted to have children, and I would never give up that experience for a career. I want to have it all.”

October 2005
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Brad and Jen's divorce is finalized.

December 2008
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Jen talks Brad and Angelina again, this time with Vogue. She explains that she was hurt by stories Brangelina shared with the press about falling for each other during their marriage.

"There was stuff printed there that was definitely from a time when I was unaware that it was happening," she says. "I felt those details were a little inappropriate to discuss. That stuff about how she couldn't wait to get to work every day? That was really uncool."

September 2011
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Brad *finally* addressed his breakup with Jen and how 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."

September 2011
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Yeah, so uh, people thought from Brad's comments he was calling Jen "uninteresting," which is, like, never the move. He later issued a statement saying, "It grieves me that this was interpreted this way. Jen is an incredibly giving, loving and hilarious woman who remains my friend. It is an important relationship I value greatly. The point I was trying to make is not that Jen was dull, but that I was becoming dull to myself—and that, I am responsible for."

September 2014
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Brad Pitt and Angelina Jolie officially marry.

Jan. 21, 2015
21st Annual Screen Actors Guild Awards - Arrivals
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Jen keeps it real and lets us known that Brad actually never did anything wrong when they were together. "We’re not in daily communication,” she said to the Hollywood Reporter. “But we wish nothing but wonderful things for each other. Nobody did anything wrong. You know what I mean? It was just, like, sometimes things [happen]. If the world only could just stop with the stupid, soap-opera bullshit. There’s no story."

August 5, 2015
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Jennifer Aniston and Justin Theroux tie the knot (or at least have a ceremony).

September 15, 2016
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Angelina Jolie files for divorce from Brad Pitt.

November 2016

Justin Theroux posts an Instagram that most definitely says "f*ck brad pitt." Is it shade? Probably not considering he edited the post to include the hashtag: "#andNOthispostisNOT'shading'anyonebecauseimnotelevemyearsoldimeanseriously."

March 2017
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It's reported that Brad and Jen are in contact. Sources say he tracked down his ex's number so he could wish her a happy birthday, and that they've "been texting." What's more, apparently Brad "told her he’s having a hard time with his split and they exchanged a few texts reminiscing about the past." Hmmmm.

December 2017

Brad Pitt starts "casually dating" in the wake of his split from Angelina Jolie, with a source saying: "He has been going out but there is nothing serious in the dating area at all, nothing to speak of at this point."

February 15, 2018
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Jennifer Aniston and Justin Theroux announce their separation. Twitter explodes with hope that Jen and Brad are getting back together, mostly in the form of Rachel Green GIFs.

February 21, 2018
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Yeah, so apparently Jen kept little love notes from Brad from when they were married. (Sweet, IMO.) Apparently Justin found them two years prior, when they were already married. Ouch.

“He stumbled upon old Post-it notes Brad had written,” said a source to Us Weekly. “Sweet little Post-its like, ‘You looked nice tonight’ or ‘Miss you already.’”

Dec. 7, 2018
Premiere Of Netflix's "Dumplin" - Arrivals
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Aniston keeps it real about both of her marriages in an interview with ELLE. "I don't feel a void. I really don't. My marriages, they've been very successful, in [my] personal opinion," she said. "And when they came to an end, it was a choice that was made because we chose to be happy and sometimes happiness didn't exist within that arrangement anymore."

February 9, 2019
Premiere Of Universal Pictures' "Wanderlust" - Arrivals
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Jen celebrated her 50th birthday with a star-studded party at the Sunset Tower Hotel in Los Angeles. Brad, who was spotted at the venue, was among the guests, according to People.

June 5, 2019
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After reports of Brad being seen at Jen's 50th birthday bash, everyone had one question: "Are you getting back together, or no?"

Brad responded to the forever-asked-question to a hounding paparazzi cameraman by merely saying, " Oh my god," before stepping into his car and telling the cameraman to "have a good one." So, uh, mood?

August 6, 2019
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Don't freak out, but Jen is definitely back in the dating game, reports ET. Her Friends co-stars encouraged her to get back in the saddle, so she's been casually treading the waters. Also, she's still in contact with Brad, a source told the outlet, and they talk occasionally.

Dec. 16, 2019

So, Jen threw an "intimate" holiday bash for her close friends...and guess who came? You guessed it: Brad. According to Entertainment Tonight: "[Brad] was among the first to arrive and the second to last guest to leave around 11 p.m." Other guests at the star-studded (but intimate!) party included Gwyneth Paltrow, Tom Hanks, Kate Hudson, Lisa Kudrow, and Reese Witherspoon.

Dec. 25, 2019
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Is this a Christmas miracle? A source tells Us Weekly that Brad and Jen "have a wonderful connection that might seem flirtatious at times." Um, what! The source went on to say, "They dig each other’s sense of humor and have an infectious energy when they’re together, but they insist things are purely platonic and nothing more than that."

Jan. 19, 2020
26th Annual Screen Actors Guild Awards - Media Center
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Now self-professed "good friends," Jen and Brad's support of each other was on full show at the 2020 SAG Awards. First, Brad cracked a joke about his failed marriages, and Jen laughed and applauded; then Jen won an award, and Brad watched tenderly from backstage. Then they ran into each other afterwards and were photographed together for the first time in years. Plus, is this body language a little flirty, or is it just me?

Jan. 22, 2020
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It's a couple of days after the storm, and my life has not known peace since. To make matters worse (but honestly better), a source tells People that the reunion was accepted happily. "They are friends and happy for each other. They want nothing but happiness for each other," said the source. "She is happy to have Brad back in her life as a friend, but that's it."

January 31, 2020

Word gets out that Brad and Jen share the same stylists, duo Nina and Clare Hallworth, and everyone loses their sh*t. Unfortunately, they've never styled them for the same event, but a girl can dream.

April 1, 2020
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In some kind of sick April Fools joke, a bunch of tabloids start to spread a fake story that Brad and Jen are dating and planning a secret Mexican beach wedding. They even went as far as to say Jen's ex Justin Theroux was on the guest list. Riiiight. Yeah, let's just say this has yet to happen.

June 14, 2020
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Word gets out that Brad matched Jen's $1 million donation to Color of Change following the death of George Floyd.

"Brad is ­really involved with the charity because of Jen and said he would match her donation," a source told The Mirror. "He went to the protests this week and was at her home the day after. They are both very ­passionate and want to help as much as they can."

September 4, 2020
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Brad is seen with his new girlfriend, Nicole Poturalski, at the very same French castle where he and Angelina married in 2014. Why is this big drama, you may ask yourself? Because it was on the SAME DAY as their wedding anniversary.

A source close to Brad told Us Weekly, "He just doesn't care if Angelina is going to lash out. He expects she will." The most awkward part of all? They're *still* not officially divorced, even all these years later.

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