Perhaps that’s why some of us maintain hope that they will eventually reunite. After surviving second marriages and divorces (Pitt to Angelina Jolie and Aniston to Justin Theroux), the two seem to be on friendly terms these days. For the sake of nostalgia, we’re looking back at the history of Brad and Jen’s sensational relationship.
In a 2001 interview with Rolling Stone, Aniston explained that she first met Pitt casually in 1994 through their managers.
“He was just this sweet guy from Missouri, you know?” she said. “A normal guy.”
Both were in relationships at the time—Aniston with actor Tate Donovan, Pitt with Gwyneth Paltrow. But by 1998 the two were single again. That’s when their managers played matchmaker and set them up on a date.
The pair initially kept things quiet. However, once the news was out, Aniston’s friends gave her new beau their seal of approval.
“My friends were all supportive,” Aniston said, “especially when they found out what a loving human being Brad is. At first they’re like, ‘I hope he’s not an asshole, some conceited [expletive] or whatever.’ But you get past that in five minutes.
Which is a real tribute to who he is. He just disarms you immediately. But, I mean, nobody went, ‘Dude. Brad Pitt!’ and gave me a thumbs up and a wink. They were just happy for me.”
A few years later, on a 2004 episode of ABC’s Primetime, Aniston told Diane Sawyer the two knew right away that they were a match.
“We both did, on our first date,” said Aniston. “I thought … mmm. That’s weird. That was a really easy evening. That was really fun.”
In 2005, Aniston told Vanity Fair that their initial secrecy was something she really valued about the relationship. “We had so much fun falling in love,” she said. “It was so private; we kept it to ourselves for so long. It was something we were really proud of.”
Remember the days before couples went Insta-official to proclaim they were off the market? In September 1999, while tabloids were in a frenzy to confirm their relationship status,
Brad and Jen made their first official appearance as a couple at the Emmy Awards. (Between Brad’s sunglasses and Jen’s dreadlocks, the two apparently wanted to their big moment to double as a fashion statement.)
That November, just months after going public, the pair crashed the stage at a Sting concert in New York City. With the iconic rock star standing by their side, Aniston and Pitt revealed a shiny new engagement ring to the massive audience.
The couple later settled a $50 million lawsuit with jeweler Silvia Damiani, who designed the ring for an estimated $500,000. Damiani was sued for using the celebs’ names and faces to sell cheaper knock-offs of the design.
Forget eloping—Brad and Jen wanted a wedding fit for the level of fame. On July 29, 2000, the two were married before 200 guests at a lavish ceremony in Malibu.
The two spared no expense on their big day—event planners estimated that the event cost at least $1 million. After exchanging vows on a Malibu bluff (with Aniston promising to always make Pitt his “favorite banana milk shake”), they moved on to a reception that included 50,000 flowers, four bands, a 40-member gospel choir, an endless parade of lobster and caviar, and a 13-minute fireworks show.
As extravagant as it was, the wedding was only meant to be enjoyed by its guests. Staffers were required to sign NDAs that made them liable for a $100,000 penalty if they leaked details of the event.
In 2001, Pitt appeared on a Thanksgiving episode of Friends. “The One With the Rumor” cast Pitt as a character who hates Rachel Green. It ranks as the best guest appearance in the history of the show.
More importantly, it was a great show of support for his wife’s career. But in 2004, as Friends wound down its 10-year run, Aniston began making plans for the future.
“It’s time [for a family],” she told The Guardian in 2004. “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.”
However, she showed a practical side when talking about her potential partner in parenthood.
“I’ve never been someone who says, ‘He’s the love of my life,'” Aniston said in 2003 interview with W. “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.”
Aniston, who was reluctant to share a definitive baby-making timetable, told the Guardian that it would have to happen after certain projects had wrapped.
“I’ll have finished Friends by end of January, [Brad] will be finishing [Mr. and Mrs. Smith, opposite Angelina Jolie] at the end of February,” she said. “Then he starts Ocean’s Twelve. So I, thankfully, will be able to go and travel with him while he’s doing that.”
Alas, Pitt’s role in Mr. and Mrs. Smith would be the gig to doom his marriage. Rumors that he was cheating with co-star Angelina Jolie sprung up instantly, and by January 2005, Jen and Brad announced their separation.
“We would like to announce that after seven years together we have decided to formally separate,” they wrote in a statement to People. “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.”
His co-star initially denied allegations that they fell in love on the set of the movie. In 2005, Jolie told Marie Claire, “To be intimate with a married man, when my own father cheated on my mother, is not something I could forgive. I could not, could not look at myself in the morning if I did that.”
However, in the January 2007 issue of Vogue, she begins to change her tune. “I think we were the last two people who were looking for a relationship,” said Jolie. “I certainly wasn’t. I was quite content to be a single mom.”
“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.’ … 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.”
“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.”
Pitt and Aniston’s divorce was finalized in October of 2005. And we all know, Pitt and Jolie were hitched until 2016, when Angie filed for divorce.
Brad’s second divorce, combined with Aniston’s reputation as America’s sweetheart, has fueled constant rumors that they are working towards reconciliation.
Despite wild speculation that their split devastated Jennifer to the point of starvation, or that the two are rekindling their romance over secret getaways, the truth is that the two have settled on friendship. (Sorry folks, that means there’s no secret baby hiding out in an LA mansion or Brad’s French castle.)
Here’s what we do know to be true: in 2019, Pitt was a happy guest at Aniston’s 50th birthday bash. A source told ET that Aniston put her ex-husband on the guest list when he was in town, and that Pitt “wanted to support” Aniston because the two have “been friendly” in recent years.
The two also reunited on Zoom this past October for a virtual table read of Fast Times at Ridgemont High. Their simple exchange of “hellos” was enough to cause a stir. But once they dove into the script, fans went into full-blown freakout mode.