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Jennifer Aniston and Brad Pitt

How Long Were Jennifer Aniston & Brad Pitt Together?

Gettyimages | Kevin Winter
By Jordan White

Jennifer Aniston and Brad Pitt go way back. From being the hottest Hollywood couple to friendly exes, these two have been in each other’s lives for a long, long time.

Which explains why the internet would love to see them together again, in a non-platonic way. Especially now that they’re both single.

And while the idea seems far-fetched, anything could happen with the complicated history they have.

In the meantime, here’s a look inside their relationship, and how long they were actually together.

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Jennifer Aniston
Jennifer Aniston/Instagram

Aniston and Pitt first met in 1994, through their managers. But the couple didn’t go on their first date until 1998.

In 1999, Pitt and Aniston made their red carpet debut at the Emmy Awards. That same year, the two announced their engagement while at a Sting concert.

The couple’s wedding was held in Malibu and the ceremony was apparently classy as could be. There were even fireworks!

One year after their wedding, Aniston discussed her marriage with Rolling Stone.

Jennifer Aniston
Jennifer Aniston/Instagram

'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,' she said.

In 2003, Aniston revealed whether or not Pitt was the ‘love of her life.’ And her response was a little confusing.

'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,’ she explained during an interview with W magazine.

Brad Pitt and Angelina Jolie
Gettyimages | Anthony Harvey

‘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 added.

In early 2004, Aniston opened up about her desire to start a family with Pitt.

'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,’ she told The Guardian.

However, a couple of months later, Pitt was cast alongside Angelina Jolie in ‘Mr & Mrs. Smith.’

Jennifer Aniston
Jennifer Aniston/Instagram

In January 2005, Aniston and Pitt announced their separation. Shortly after, Pitt and Jolie started dating.

In October of that year, Aniston and Pitt's divorce was finalized.

Afterward, both Pitt and Jolie discussed how they fell in love while filming the ‘Mr & Mrs. Smith’ movie.

‘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,’ Jolie revealed.

Naturally, Aniston wasn’t too pleased with their press.

‘There was stuff printed there that was definitely from a time when I was unaware that it was happening. 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,’ Aniston told Vogue.

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