Inside Brad Pitt and Jennifer Aniston’s dream romance before it turned to nightmare

Brad Pitt and Jennifer Aniston seemed to be the perfect Hollywood couple.

They first encountered each other in a casual meeting through their managers – who just happened to be friends – in 1994, but didn’t go on their first date until four years later.

After they hooked up, the A-listers became one of the most beloved showbiz couples of all time, with people around the world heavily invested in their relationship.

Sadly, things weren’t to last, and their marriage broke down after five years, and after he met second wife Angelina Jolie on the set of Mr & Mrs Smith.

Despite their very bumpy up and downs, the stars are great friends all these years later, and they’ve even sparked hopes that they’ll get back together after Brad’s split from Ange.








Brad and Jennifer first met in 1994 but went on their first date four years later
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Image:

Getty Images)



On what would have been their 21st wedding anniversary, we take a look back at Brad and Jen’s rollercoaster relationship and their fairytale wedding…

1994

Brad and Jen met for the first time through their managers, who happened to be friends.

Recalling the moment in an interview with Rolling Stone in 2001, she said: “He was just this sweet guy from Missouri, you know? A normal guy.”

1998

Four years after that casual meeting, they were set up by their managers on a date.

Brad had just split from Gwyneth Paltrow and Jen had ended her romance with Tate Donovan.

Looking back in 2004, Jen said that first night together had been “really easy” and “really fun”.

September 1999

Brad and Jen made their official red carpet debut on September 12, 1999, walking hand-in-hand into the 51st Primetime Emmy Awards.

Until then, their romance was only a rumour.








They made their red carpet debut in 1999
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Image:

Ron Galella Collection via Getty Images)



November 1999

Brad and Jen revealed they were engaged on stage at a Sting concert on November 29, 1999.

They were pictured on stage alongside the rocker, with Brad holding up Jen’s hand to proudly show off her new accessory.

It was rumoured he’d spent a whopping $500,000 on the ring.

July 2000

Brad and Jennifer said ‘I do’ in a beautiful fairytale wedding on July 29, 2000.

Theirs was undoubtedly the biggest celebrity wedding of the year, with fans around the world desperate for a peek inside.

They tied the knot on a bluff overlooking the Pacific Ocean in Malibu, with 200 guests there to cheer them on.

Brad shelled out for 50,000 roses, wisteria, tulips and lotus flowers in a bid to make the stunning venue look like a Zen garden.

Jen made an incredibly beautiful bride, wearing a glass-beaded wedding gown with a low back, designed by Lawrence Steele.







Showing off Jen’s engagement ring on stage with Sting



And when it came to their first dance, they twirled and swayed on the dancefloor to The Way You Look Tonight.

Their big day also included a 40-person gospel choir, a fancy lobster meal and champagne and a performance by Melissa Etheridge.

It was all rounded off with a 13-minute fireworks display and the whole thing is believed to have cost around $1 million.

November 2001

Brad was one of Hollywood’s biggest stars when he filmed a much-talked-about guest spot on Jen’s hit sitcom Friends.

Appearing in episode The One With The Rumour, he played an old classmate of Rachel Green.

Rachel didn’t remember his character, but he hated her as she’d teased him for being overweight.

Years later, he’d lost weight and caught Rachel’s eye with his hunky looks, but of course, he wasn’t interested.

February 2004

With Friends soon to come to an end, Jennifer said in an interview that she was ready to have a baby.

She told The Guardian: “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

Jen’s baby dream with Brad wasn’t to be as cheating rumours began to swirl in May 2004 while he was filming Mr & Mrs Smith with Angelina Jolie.

Later in 2006, a year after his divorce from Jen, Angelina said they had fallen for each other on the set of the film.

She told 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 realised, ‘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 realise 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.”








Brad and Angelina met on the set of Mr & Mrs Smith
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Image:

Reuters)



January-March 2005

Brad and Jen announced they were getting a divorce in January 2005, after seven years together and almost five years of marriage.

And they insisted at the time that their split was nothing to do with the rumours surrounding Brad and Angelina.

They said in a joint statement to People: “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.”

Jennifer officially filed for divorce on March 25 of that year.

September-October 2005

Brad had gone public with Angelina by this point, but it took months for Jennifer to officially address the split.








The couple divorced in 2005
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Image:

Getty Images)



She told Vanity Fair: “Am I lonely? Yes. Am I upset? Yes. Am I confused? Yes. Do I have my days when I’ve thrown a little pity party for myself? Absolutely. But I’m also doing really well.

“Relationships are two people; everyone is accountable. A lot goes into a relationship coming together, and a lot goes into a relationship falling apart.”

And when told about a 60-page photo spread that Brad and Angelina had just done with W Magazine, Jennifer responded: “Is it odd timing? Yeah. But it’s not my life. He makes his choices. He can do whatever. We’re divorced, and you can see why.

“I can also imagine Brad having absolutely no clue why people would be appalled by it. Brad is not mean-spirited; he would never intentionally try to rub something in my face.”




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Their divorce was finalised on October 2, 2005.

September 2011

Years after their split, Brad made some rather unsavoury comments about his marriage to Jennifer.

He told Parade at the time: “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. I think that my marriage had something to do with it. Trying to pretend the marriage was something that it wasn’t.”

But he later apologised for what he’d said, 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.”

August 2012

Jennifer got engaged once more when her boyfriend of one year, actor Justin Theroux, popped the question.








Jennifer got engaged to Justin in 2012
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Image:

Getty Images)



And similarly to Brad, it’s thought that he used a $500,000 engagement ring when he asked the actress to be his wife.

August 2014

After years of raising their six children together, Brad and Angelina eventually tied the knot on August 23, 2014.

Their wedding was attended by only 22 family members, including the kids, Maddox, Pax, Zahara, Shiloh, Vivienne, and Knox.

The intimate nuptials were held at their French chateau.

August 2015

Jennifer’s second marriage came just one year after Brad’s when she tied the knot with Justin.

September 2016

In an announcement that shocked the world, Angelina filed for divorce from Brad in September 2016, citing irreconcilable differences.








Brad and Jen way back in 2000
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Image:

Reuters)



February 2018

Jennifer announced she was splitting from husband Justin on February 15, 2018.

February 2019

Now that Brad and Jen were both single, reunion rumours were rife when he was invited to her 50th birthday party in 2019.

While sources close to them continued to insist they were nothing more than good friends, fans continued to hold out hope that they’d get back together.

January 2020

The internet went into complete meltdown in 2020 when Brad and Jen were pictured together on the red carpet at the Screen Actors Guild.

And to make things even more exciting, they were snapped holding hands, with Jennifer appearing to lead the way while Brad kept a tight hold of her as he followed behind.

Their flirtatious body language got everyone talking, and people were more hopeful than ever that they’d spark up their romance once more.








Pictures like this get fans very excited about a reunion
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Image:

Getty Images for Turner)



September 2020

Brad and Jen broke the internet AGAIN when they played two flirty characters in a charity table read of 1982 movie Fast Times at Ridgemont High.

People were particularly giddy over this because Brad’s character shared his name, meaning a clip of Jennifer quickly went viral thanks to her line: “Hi Brad, you know how cute I always thought you were? I think you’re so sexy, will you come to me?”

June 2021

Remaining firm friends after all they’ve been through, Jennifer gushed about her friendship with Brad in June 2021 as she spoke about their famous table read.

She said on SiriusXM’s The Howard Stern Show: “Brad and I are buddies, we’re friends.








They sparked more rumours when they did a table read together
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Image:

CORE)



“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 added: “We had fun, and it was for a great cause.”

And when asked about the speculation that were going to get back together, she said: “It’s hysterical, but what else are [people] gonna talk about?”





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