Brad Pitt & Jennifer Aniston relationship from first date to heartbreaking split

Jennifer Anniston and Brad Pitt quickly became Hollywood’s ‘It’ couple when they first went public with their romance in 1998.

After the pair were set up on a date by their agents, the duo went on to marry, becoming one of the most-loved couples in showbiz history.

However, the good times ended when Jennifer filed for divorce five years later citing “irreconcilable differences”.

Marking 20 years since the pair exchanged vows, Daily Star Online looks back at the former couple’s relationship timeline.

First date – 1998

Actor Brad Pitt and actress Jennifer Aniston went public at the Emmy Awards in 1999 (Image: Ron Galella Collection via Getty Images)

The pair reportedly met after they were set up on a date by their agents in 1998, but met four years prior.

According to the Friends star, she and the actor crossed paths in 1994 because their agents were friends.

Speaking at the time, before they started dating, Jen said: “He was just this sweet guy from Missouri, you know? A normal guy.”

After Brad called time on his engagement to Gwyneth Paltrow and Jen ended her relationship with Tate Donovan – their respective agents decided to play matchmaker – and set them both up.

A year later, they made their red carpet debut at the Emmy Awards with the actor rocking Matrix-style sunglasses and an all-black ensemble while Jennifer sported a glitzy gold number.

Engagement – 1999

The couple became engaged in 1999 – a year after they started dating (Image: Reuters)

Months after going public with their romance at the Emmys, the couple announced they were engaged in November 1999.

With no social media back then, the lovebirds crashed the stage of a Sting concert in New York City and revealed they were set to walk down the aisle as Jen flashed her large engagement ring.

Idyllic wedding – 2000

The pair married on July 29 2000 in a lavish Malibu ceremony (Image: Reuters)

Almost a year later, Pitt and Aniston pulled out all the stops for their lavish Malibu wedding.

According to PEOPLE magazine, 200 guests attended, 50,000 flowers were used, four bands, and a gospel choir performed, and fireworks wrapped up the festivities.

The Horrible Bosses star told Rolling Stone in 2001: “I had those typical jitters the day before my wedding, but the day of, I was just excited in a good way.”

Brad stars in Friends – 2001

Brad Pitt played Will Colbert in episode “The One With The Rumor” in season eight of Friends (Image: NBCUniversal via Getty Images)

Jennifer portrayed Rachel Greene in Friends since its inception on NBC in 1994.

Following their nuptials, Brad made a guest appearance on season eight of the show, in the episode titled “One With the Rumour”.

Playing Rachel’s nemesis Will Colbert, a high school friend of Ross Gellar (David Schwimmer), who co-created a club against her called “The I Hate Rachel Greene” Club.

When asked who the other co-founder was he reveals that Ross was, surprising Rachel.

Jennifer confession – 2003

Jennifer opened up about wanting to start a family with her husband during an interview with The Guardian in 2004 (Image: Ron Galella Collection via Getty Images)

During an interview with W magazine, she was asked how it felt to find the love of her life, Brad Pitt.

She replied: “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.”

Pregnancy talk – 2004

The Horrible Bosses star revealed she wanted to start a family with Brad after Friends wrapped its tenth season (Image: Getty Images)

Following the finale of Friends airing in 2004, Jennifer opened up about her desire of wanting a family in an interview with The Guardian.

“Yeah. 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,” she told the publication.

“So I’m just truly looking forward to slowing down.”

Mr and Mrs Smith – 2004

The duo meet on Mr and Mrs Smith but shoot down romance rumours (Image: Reuters)

Brad Pitt and Angelina Jolie meet on the set of Mr. and Mrs. Smith in 2004 – and while there were rumours about a could-be romance, the pair insisted they were just “good friends”.

Angelina later described how she fell for Brad on set, admitting to Vogue the pair found themselves in a “strange friendship”.

“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’,” she said.

Heartbreaking divorce – 2005

The pair confirmed they have separated in a joint statement (Image: Getty Images)

Less than a year later, in January 2005, the couple announced they had separated and released a joint statement.

It read: “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.”

In November, their divorce was finalised.

Brad marries Angelia Jolie – 2014

Brad and Angelina married in 2014 but two years later the actress filed for divorce (Image: Getty Images)

Brad and Angelina wed in 2014, following nine years of dating.

Angelina Jolie filed for divorce from Brad Pitt, citing irreconcilable differences in 2016.

She requested primary custody of their six children, and the couple’s lawyer, Robert Offer, released a statement: “This decision was made for the health of the family. She will not be commenting, and asks that the family be given its privacy at this time.”

Reunion at Sag Awards – 2020

The former lovebirds reunited at the SAG Awards 2020 (Image: Getty Images for Turner)

At the 2020 SAG Awards, the former lovebirds embraced – causing a meltdown on the World Wide Web.

Cameras caught the moment they greeted each other with an embrace and lots of hand-holding.

As he watched Jen take home Outstanding Performance by a Female Actor in a Drama Series for her work in The Morning Show, Brad gasped “oh wow”.

Accepting his award, Brad cracked a joke about his failed marriages, and Jen, who was in the audience, laughed and applauded.

Source: Celebrities - dailystar.co.uk

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