Jennifer Aniston and Brad Pitt's Relationship: A Look Back

Evan Agostini/Getty

Despite enduring one of the most high-profile splits in Hollywood, Jennifer Aniston and Brad Pitt remain "buddies" over 15 years later.

The actors were introduced by their managers and secretly dated before tying the knot in a lavish 2000 ceremony. Ultimately, they called it quits in 2005 and went on to wed other people, Pitt to his Mr. & Mrs. Smith costar Angelina Jolie and Aniston to actor Justin Theroux.

"I really do hope that someday we can be friends again," Aniston told Vanity Fair in the wake of their split. "I will love [Brad] for the rest of my life. He's a fantastic man. I don't regret any of it, and I'm not going to beat myself up about it," she continued.

In recent years, the former pair have appeared to rekindle their friendship, delighting fans with not one, but two reunions in 2020: a warm backstage embrace at the SAG Awards that quickly went viral and a virtual table reading of Fast Times at Ridgemont High.

From their first date to their renewed friendship, here's a timeline of Jennifer Aniston and Brad Pitt's relationship.

1994: Jennifer Aniston and Brad Pitt first meet

Aniston and Pitt were introduced by their managers in the mid-'90s, years before their relationship turned romantic. "He was just this sweet guy from Missouri, you know?" Aniston later recounted to Rolling Stone of her first impression of her future husband. "A normal guy."

1998: Jennifer Aniston and Brad Pitt go on their first date

With both Aniston and Pitt newly single — she split from actor Tate Donovan and he recently called off his engagement to Gwyneth Paltrow — their managers brought them together once again. This time, they hit it off.

"That was a really easy evening. It was really fun," Aniston later told Diane Sawyer of their immediate chemistry.

September 12, 1999: Jennifer Aniston and Brad Pitt make their red carpet debut

Ron Galella, Ltd./Ron Galella Collection via Getty

The couple kept their romance under wraps for the first few months, before making their highly-anticipated red carpet debut at the 1999 Emmy Awards. The duo hit the carpet in particularly memorable looks, with Pitt wearing a pair of silver sunglasses and Aniston in a sequined dress.

November 21, 1999: Jennifer Aniston and Brad Pitt announce their engagement

During a Sting concert at New York City's Beacon Theater, the couple took the stage to show off Aniston's new bling: a diamond-and-platinum engagement ring from Italian jewelry designer Silvia Damiani, which PEOPLE reported that Pitt spent seven months helping design.

July 29, 2000: Jennifer Aniston and Brad Pitt get married

Surrounded by 200 of their friends, family and costars, the couple exchanged heartfelt vows — with Aniston promising to always make Pitt's "favorite banana milk shake" — beside the beach in Malibu, California. The lavish nuptials featured 50,000 flowers, four bands, a 13-minute fireworks display and more. The bride wore a silk-and-satin beaded gown by Lawrence Steele for the special day. Event planners estimated the wedding day may have cost $1 million.

September 10, 2000: Jennifer Aniston and Brad Pitt make their red carpet debut as a married couple

Ron Davis/Getty

Just one year after their initial red carpet debut, the duo stole the spotlight when they arrived at the 2000 Emmy Awards, marking their first red carpet appearance as husband and wife.

November 2001: Brad Pitt guest stars on an episode of Friends

The actor memorably joined his then-wife on-screen for the first time in the Thanksgiving episode of season 8 of Friends, "The One with the Rumor." He played Will Colbert, who launched an "I Hate Rachel Green Club" in high school. Aniston later revealed that he was one of her favorite guest stars, saying, "Mr. Pitt was wonderful."

January 20, 2002: Jennifer Aniston and Brad Pitt attend the Golden Globes

Frank Trapper/Corbis via Getty

The couple served up another iconic red carpet look with their matching moment at the 2002 Golden Globes, where Aniston was nominated for the first time. The duo coordinated in black suits and their signature blond highlights.

2002: Jennifer Aniston and Brad Pitt launch a production company, Plan B Entertainment

In 2002, Aniston and Pitt co-founded Plan B Entertainment alongside producer Brad Grey. "We started this little company underground, didn't really talk about it because we didn't want to be accused of being actors who have vanity deals where you don't do anything," Aniston told The Guardian in 2004.

Soon, things "snowballed" and the company had 17 films in production, including 2004's Troy (starring Pitt) and 2005's Charlie and the Chocolate Factory. When the pair split in 2005, Pitt became the company's sole owner, with Grey leaving to head up Paramount Pictures.

February 2003: Jennifer Aniston questions if Brad Pitt is the love of her life

During an interview with W Magazine in which the interviewer referred to Pitt as the love of Aniston's life, the actress responded that she wasn't a big fan of the phrase.

"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 told the outlet. "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."

February 2004: Jennifer Aniston says "it's time" to start a family with Brad Pitt

Ian West - PA Images/PA Images via Getty

Speaking to The Guardian, the Along Came Polly star revealed that she was ready 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 outlet.

January 7, 2005: Jennifer Aniston and Brad Pitt announce their separation and say that they "remain committed and caring friends"

Just a few days after the pair were photographed spending New Year's Eve in Anguilla, they revealed their split to PEOPLE exclusively.

"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," the actors said in a joint statement. "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."

March 25, 2005: Jennifer Aniston files for divorce from Brad Pitt

The Break-Up star officially filed for divorce from the actor in Los Angeles Superior Court two months after they announced their split. Her court papers cited irreconcilable differences, PEOPLE reported. She also requested to restore her last name from Pitt back to Aniston. The divorce was finalized later that year on Oct. 2.

September 2005: Jennifer Aniston addresses rumors surrounding her split from Brad Pitt

Jim Smeal/Ron Galella Collection via Getty

In a candid and wide-ranging interview with Vanity Fair, Aniston opened up about mourning her marriage, her reaction to the barrage of headlines surrounding Pitt's budding relationship with Jolie and her desire for everyone to just "move on" already.

"There are many stages of grief," Aniston said. "It's sad, something coming to an end. It cracks you open, in a way — cracks you open to feeling. When you try to avoid the pain, it creates greater pain. I'm a human being, having a human experience in front of the world. I wish it weren't in front of the world. I try really hard to rise above it."

At one point, she shared her reaction to the viral photos of Pitt and Jolie, who had been denying romance rumors up until then, on vacation together in Kenya.

"I can't say it was one of the highlights of my year," she said. "Who would deal with that and say, 'Isn't that sweet! That looks like fun!'? But s--- happens. You joke and say, 'What doesn't kill you makes you stronger.' "

She continued, "I would much rather everyone move on. I am not defined by this relationship. I am not defined by the part [the media is] making me play in the triangle. It's maddening to me."

September 6, 2007: Brad Pitt speaks about the divorce, says that he and Jennifer Aniston "maintain a deep friendship"

Two years following their high-profile split, the Jesse James actor told V magazine that he and Aniston were still close. "Jen and I still maintain a deep friendship and have a lot of life together that isn't erased in any way," he said.

Speaking about their split, he added, "I don't know how better to have handled [it]. My view was, this was no one's business in the end — at least in matters of the heart. The thing guiding me then was, you don't know how many days you have, and you need life to be everything you need it to be."

September 2011: Brad Pitt says he "wasn't living an interesting life" during his marriage to Aniston

Ron Galella, Ltd./Ron Galella Collection via Getty

Six years after their split, Pitt spoke to Parade about his marriage to Aniston — and swiftly walked back his comments, which he felt were misinterpreted. "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 [to Aniston] had something to do with it. Trying to pretend the marriage was something that it wasn't," he told the outlet.

Fans interpreted the statement to mean that the Moneyball actor found his life with Aniston uninteresting, which he was quick to correct.

"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," he said in a statement.

August 2014: Brad Pitt weds Angelina Jolie at their estate in France

Pitt and Jolie, who got engaged in 2012, tied the knot at their 35-room winegrowing estate Château Miraval in Correns, France.

August 5, 2015: Jennifer Aniston marries Justin Theroux

Aniston also moved on after Pitt, getting engaged to Mulholland Drive actor Theroux in August 2012. Three years later, the couple wed in a surprise ceremony in front of 70 loved ones at their shared home in Bel Air, California.

"Guests were told it was a birthday party for Justin," a source told PEOPLE. "Jen and Justin wanted to surprise guests and guests were certainly surprised."

September 15, 2016: Angelina Jolie files for divorce from Brad Pitt after 2 years of marriage

Initiating what would go on to become one of Hollywood's most high-profile (and ongoing) divorce battles, Jolie cited irreconcilable differences for her split from Pitt. She requested physical custody of the couple's six children — Maddox, Pax, Zahara, Shiloh, Vivienne and Knox — and visitation rights for Pitt.

In a statement to PEOPLE, Pitt said, "I am very saddened by this, but what matters most now is the well-being of our kids. I kindly ask the press to give them the space they deserve during this challenging time."

February 2018: Jennifer Aniston and Justin Theroux split

After nearly three years of marriage, Aniston and Theroux announced their split in February 2018.

"In an effort to reduce any further speculation, we have decided to announce our separation," said a statement released by Aniston's publicist. "This decision was mutual and lovingly made at the end of last year. We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship."

December 2018: Jennifer Aniston describes her past marriages as "very successful"

For the January 2019 issue of Elle, Aniston opened up about her marriages to Pitt and Theroux, saying that just because they ended doesn't mean they weren't valuable.

"My marriages, they've been very successful, in [my] personal opinion," she said. "And when they came to an end, it was a choice that was made because we chose to be happy, and sometimes happiness doesn't exist within that arrangement anymore."

February 9, 2019: Brad Pitt attends Jennifer Aniston's 50th birthday party

Ron Galella, Ltd./Ron Galella Collection via Getty

Once again proving that there's no bad blood between them, the actor was spotted at Aniston's 50th birthday bash at the Sunset Tower Hotel in Hollywood in February 2019. They weren't the only former flames in attendance: Aniston's other ex John Mayer made an appearance, as well as Pitt's ex Paltrow.

January 19, 2020: Jennifer Aniston and Brad Pitt reunite at the SAG Awards, sparking relationship rumors

Emma McIntyre/Getty Brad Pitt and Jennifer Aniston at the 2020 Screen Actors Guild Awards

Fans were delighted to see the two actors reunite backstage during the 2020 SAG Awards, where viral photos of the pair's warm exchange sparked hope for a romantic reconciliation between them.

"Jen was happy for Brad," a source told PEOPLE of the encounter. "They congratulated each other and that was it." Both actors took home a SAG Award in their respective categories: Pitt for Once Upon a Time… in Hollywood and Aniston for The Morning Show.

September 18, 2020: Jennifer Aniston and Brad Pitt reunite on-screen for the first time since their divorce

Marking the first time that the former pair shared the screen since their divorce, they joined an A-list cast for a virtual table read of Fast Times at Ridgemont High, reenacting the 1982 classic to raise money for Sean Penn's nonprofit CORE (Community Organized Relief Effort) and REFORM Alliance.

The actors portrayed romantic interests Brad Hamilton and Linda Barrett, even sharing a steamy moment in which Pitt's character has a sexual fantasy about Linda — which prompted an exchange between the two exes that fueled lots of laughter from their costars. The reading brought together a star-studded cast that included Julia Roberts, John Legend, Sean Penn, Matthew McConaughey, the late Ray Liotta and more.

June 23, 2021: Jennifer Aniston says she and Brad Pitt are "buddies"

During an appearance on Howard Stern's eponymous SiriusXM show, Aniston confirmed that her and Pitt's September virtual reunion was "absolutely fun," rather than awkward.

"Brad and I are buddies, we're friends," Aniston said. "And 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 continued. "We had fun, and it was for a great cause, [Sean Penn's community relief nonprofit] CORE."

May 26, 2022: Jennifer Aniston reveals that she began therapy after her split from Brad Pitt

Jeff Kravitz/FilmMagic

During the series finale of The Ellen DeGeneres Show, Aniston told the talk show host — who is a longtime friend — that the end of her marriage to Pitt marked the beginning of a whole new chapter for her, which coincided with the end of Friends' 10-season run.

"Well, I got a divorce and went into therapy," Aniston said. "And then I did a movie called The Break-Up," she continued. "I just kinda leaned into the end. I just was like, 'You know what, guys? Let's make this a completely new chapter. Let's just end everything and start new.' It worked great."

November 9, 2022: Jennifer Aniston addresses hurtful pregnancy rumors after her split from Brad Pitt

Aniston opened up about painful pregnancy rumors that plagued her for years, revealing that she had been struggling with infertility. "I was trying to get pregnant. It was a challenging road for me, the baby-making road," Aniston told Allure.

"All the years and years and years of speculation… It was really hard," she added. "I was going through IVF, drinking Chinese teas, you name it. I was throwing everything at it. I would have given anything if someone had said to me, 'Freeze your eggs. Do yourself a favor.' You just don't think it."

She also spoke about how her split from Pitt sparked rumors that she chose her career over having kids. "It was absolute lies," the actress said of the "narrative that I was just selfish... I just cared about my career. And God forbid a woman is successful and doesn't have a child. And the reason my husband left me, why we broke up and ended our marriage, was because I wouldn't give him a kid."