Brad Pitt & Jennifer Aniston's Relationship, From How They Met to Becoming Friends Again Post-Divorce

Julie Sprankles

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It seems impossible to believe, but onetime Hollywood golden couple Brad Pitt and Jennifer Aniston have now been divorced for almost 15 years. And while they weren’t even married for half that amount of time, their relationship left an indelible mark on pop culture. Which could explain why, after more than a decade, people are still fascinated by the status of their… well, whatever it is these days.

Ever since Pitt’s split with Angelina Jolie, fans have wondered if perhaps it would even be possible for him and Aniston to reconcile. By Hollywood standards, it’s been ages since they were romantically involved — and a lot, both spoken and unspoken, has transpired between the two during that time. And yet, the exes seem to be spending more time together as of late. In mid-December, he was one of 50 friends who attended a holiday party at Aniston’s Bel-Air home, and an eyewitness told ET he was “the second to last guest to leave.”

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But even if their past is water under the bridge and they are spending time together, it’s entirely possible the two will keep things platonic. To get a sense of the many iterations their relationship has taken over the years, though, let’s take a stroll down memory lane.

1994: They meet

Before they were ever a couple, Pitt and Aniston were simply acquaintances. They first met in 1994 through their managers. At the time, he was dating Gwyneth Paltrow. In 2001, Aniston told Rolling Stone of that time, “[Pitt] was just this sweet guy from Missouri, you know? A normal guy.”

1998: They start dating

Pitt and Aniston’s relationship really was a match made in Hollywood — they were set up by their agents! But that introduction was all they needed. As Aniston later told Diane Sawyer, “We both [knew] on our first date. It was weird… That was a really easy evening. It was really fun.”

September 1999: They go public

Who could possibly forget their iconic couple’s coming-out at the ’99 Emmy Awards? Between Pitt’s shades and Aniston’s tousled hair, their peak Southern California style remains one of the most recognizable moments for the pair.

November 1999: They announce their engagement

Mere months after making their Emmy debut, the pair blows everyone’s minds by taking the stage at a Sting concert to show off Aniston’s engagement ring.

July 29, 2000: They get hitched

Ah, ’twas the wedding that launched a million early ’00s bridal dreams. Set on a Malibu bluff and featuring 200 guests, 50,000 flowers, a gospel choir, fireworks and Aniston promising to keep Pitt in banana milkshakes for life, their big day is still stan-worthy.

September 2000: They attend the Emmys (again)

A year after going public with their relationship at the Emmys, the duo returns to the annual award show as husband and wife (and looking like a bazillion bucks, no less).

2001: He cameos on Friends

In “The One with the Rumor,” Pitt hilariously appears on Aniston’s sitcom — as a character who utterly despised her! It goes down during season eight, and it lives in infamy as one of the best guest appearances in the show’s history.

2003: She hints at marital doubt

Was it the curse of the couple cameo? We may never know for sure. But doubt seemed to start to creep into the couple’s marriage around 2003 when, in February, Aniston admits she isn’t sure if Pitt is the love of her life. “I’ve never been someone who says, ‘He’s the love of my life.’ He’s certainly a big love in my life,” she told W magazine. “And I know that’s something special, especially in all the chaos.”

February 2004: She reveals she’s ready to start a family

A year after the whole “love of her life” ambiguity, things seem to have righted themselves because Aniston goes on record to say she could see herself making babies with Pitt. “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,” she told The Guardian. “So, I’m just truly looking forward to slowing down.”

May 2004: He stars in Mr. & Mrs. Smith

Alas, the warm and fuzzy feelings that came from Aniston’s comments about potential Aniston-Pitt offspring were short-lived. By May, he was starring in Mr. & Mrs. Smith, where he met his new co-star Angelina Jolie — and it didn’t take long for rumors of an on-set affair to start circulating.

January 2005: They announce their split

Less than a year later, Pitt and Aniston release a joint statement regarding their separation: “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.”

September 2005: She addresses their split for the first time

Speaking to Vanity Fair, she maintains a united front with her ex… mostly. Of their joint separation statement, she told the magazine, “What we said was true — as far as I knew. We wrote it together, very consciously, and felt very good about it. We exited this relationship as beautifully as we entered it.”

However, she also admitted that when photographs broke of Pitt and Jolie frolicking on a beach at a romantic resort in Africa, she was “shocked.” In regard to Pitt and Jolie’s now-infamous W magazine spread, Aniston famously remarked that Pitt had “a sensitivity chip missing.”

October 2005: Their divorce is finalized

And just like that, Hollywood’s sweethearts were sweethearts no more, citing irreconcilable differences for the split.

2006: Jolie shares her and Pitt’s on-set love story

In a tell-all interview with Vogue, Jolie underscores that she never intended to break up Pitt’s marriage to his “best friend.” And yet, as she tells it, they couldn’t help being drawn to each other. “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,” she confessed.

2008: Aniston addresses Jolie’s 2006 interview

Once a bit of time had passed and she’d had plenty of time to consider her feelings, Aniston decides to speak out to Vogue about the love story Jolie shared with the publication in 2006. “There was stuff printed in there that was definitely from a time when I was unaware that it was happening,” she said.

2014: Pitt marries Jolie

After nearly a decade together, Pitt and Jolie tie the knot in France.

January 2015: Aniston gives a status update on Pitt

Speaking to The Hollywood Reporter, Aniston says she and Pitt aren’t BFFs but they aren’t enemies either. “We’re not in daily communication. But we wish nothing but wonderful things for each other. Nobody did anything wrong. You know what I mean?” she said. “It was just like, sometimes things [happen]. If the world only could just stop with the stupid, soap-opera bullshit. There’s no story.”

2015: Aniston marries Justin Theroux

Around a year after Pitt and Jolie’s wedding, Aniston has one of her own. She says “I do” to fellow actor Justin Theroux at their Bel Air home.

September 2016: Jolie files for divorce

Two years into Pitt and Jolie’s marriage, she officially files for divorce from her partner of over a decade after troubling reports emerge about an altercation between Pitt and Maddox during a flight.

March 2017: He reportedly reaches out to Aniston

Sources close to Aniston claim to Us Weekly that Pitt managed to get ahold of Aniston’s phone number so that he could wish her a happy birthday — and, apparently, unload some of his troubles. “Brad told her he’s having a hard time with his split, and they exchanged a few texts reminiscing about the past,” the source alleged.

February 2018: Aniston and Theroux announce their split

Like Pitt’s marriage to Jolie, Aniston’s union to Theroux had a two-year expiration date. They release a joint statement to USA Today insisting the decision to call it quits was “mutual and lovingly made” by “two best friends who have decided to part ways as a couple.”

February 2019: He attends her 50th birthday party

Among the revelers at Aniston’s star-studded 50th birthday party was Pitt, although a source insisted they “aren’t dating or on that path.”

August 2019: A source says Aniston is ready to start dating again

However, that source specifically tells ET that Aniston doesn’t have plans to date Pitt. Rather, she’s ready to “move forward” with support from her friends (including her ex).

December 10, 2019: He claims he hasn’t been dating anyone

Opening up to the New York Times, Pitt insists that the media makes much more of his dating life than they should. “I don’t know how many women they’ve said I’ve been dating the last two or three years, and none of it’s true — I just flashed on something, but maybe it doesn’t mean anything,” Pitt said.

December 16, 2019: He attends her holiday party

Pitt really set tongues wagging when reports surfaced that not only had he attended Aniston’s holiday party but he was one of the last guests to leave.

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