How Brad Pitt and Jennifer Aniston's Relationship Has Evolved Since Their 2005 Divorce

Brad Pitt and Jennifer Aniston have certainly come a long way since their split.

Brad Pitt and Jennifer Aniston have certainly come a long way since their 2005 split.

The former couple had a big night at the 2020 Screen Actors Guild Awards, each taking home an honor -- Pitt won Outstanding Performance by a Male Actor in a Supporting Role in a Motion Picture for his performance in Once Upon a Time in Hollywood and Aniston took home the award for Outstanding Female in a Drama Series for The Morning Show.

Pitt got a laugh from his ex during his acceptance speech, in which he joked that it wasn't a stretch to play "a guy who gets high, takes his shirt off and doesn't get on with his wife." They even reunited backstage -- Pitt watched Aniston's win after his own and the two shared a sweet congratulatory moment.

Emma McIntyre/Getty Images for Turner

Aniston spoke to ET about the awards season hype surrounding her interactions with Pitt on the SAG red carpet. "It's hysterical," she said with a laugh. "But what else are they going to talk about?"

The pair also both made an appearance at the 2020 Golden Globes earlier in the year, reaffirmed that they're clearly on good terms. ET spoke with Pitt on the red carpet, where he said he was up for a run-in with his ex-wife.

"I'll run into Jen, she's a good friend. Yeah," Pitt told ET.

"The second most important reunion of her year? I understand," he jokingly continued, adding, "That was a play on Friends. They were saying that."

During the ceremony, Pitt and Aniston sat just a table away from one another. Aniston was even seen gamely laughing while Pitt made a dating joke during his acceptance speech for Best Performance by an Actor in a Supporting Role in Any Motion Picture for his role in Once Upon a Time in Hollywood.

"I want to say hi to my folks, because hey! They're back in the Ozarks," Pitt said onstage. "I wanted to bring my mom, but I couldn't, because anyone I stand next to, they say I'm dating." 

"It would just be awkward," he added, as cameras caught Aniston chuckling.

Interestingly enough, the two have been hanging out behind the scenes lately. A source told ET in December that Pitt attended his ex-wife's holiday party at her home in Bel-Air, California, further solidifying that the two are on friendly terms following their highly publicized divorce. Fans were also shocked when he attended Aniston's 50th birthday party last February.

Of course, 50-year-old Aniston and 55-year-old Pitt weren't always on the best of terms. In a memorable 2006 interview with Vanity Fair, the Friends star was remarkably candid about how painful the end of their five-year marriage was, particularly the scandal that erupted amid her already difficult split from Pitt -- when he started dating his Mr. & Mrs. Smith co-star, Angelina Jolie.

"The world was shocked, and I was shocked," she admitted of the headline-making pictures that came out of Pitt and Jolie on a beach in Africa playing with Jolie's son, Maddox, in April 2005, which all but confirmed their off-screen relationship. "I can't say it was one of the highlights of my year. Who would deal with that and say, 'Isn't that sweet! That looks like fun!'? But sh*t happens. You joke and say, 'What doesn't kill you makes you stronger.'"

"I would be a robot if I said I didn't feel moments of anger, of hurt, of embarrassment," she added.

When asked about Pitt and Jolie posing for a 2005 W magazine feature titled "Domestic Bliss" that many saw as insensitive to Aniston at the time, she again kept it real.

"Is it odd timing? Yeah. But it's not my life," she noted. "He makes his choices. He can do -- whatever. We're divorced, and you can see why."

"Brad is not mean-spirited; he would never intentionally try to rub something in my face," she continued. "In hindsight, I can see him going, 'Oh -- I can see that that was inconsiderate.' But I know Brad. Brad would say, 'That's art!' ... There's a sensitivity chip that’s missing."

Still, Aniston was always consciously striving to rise above it.

"I'm not interested in taking public potshots," she noted to the magazine at the time. "It's not my concern anymore. What happened to him after the separation -- it's his life now. I've made a conscious effort not to add to the toxicity of this situation. I haven't retaliated. I don't want to be a part of it. I don't have a halo that I'm polishing here; everyone has their personal thoughts. But I would much rather everyone move on."

Meanwhile, Pitt wasn't exactly complimentary when alluding to his marriage to Aniston in a 2011 Parade interview.

"I spent the '90s trying to hide out, trying to duck the full celebrity cacophony," he said. "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."

"I put much more emphasis on being a satisfied man," he also told the magazine. "I'm satisfied with making true choices and finding the woman I love, Angie, and building a family that I love so much. A family is a risky venture, because the greater the love, the greater the loss.  … That's the trade-off. But I'll take it all."

He later apologized for the comments after some accused him of saying Aniston was uninteresting.

"It grieves me that this was interpreted this way," he said in a rare public statement. "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."

But by January 2015, Aniston was definitely over those constantly pitting her against 44-year-old Jolie.

"I think that's slowly coming to an end. I really do," she told ET at the 2015 Critics' Choice Awards about talk of their reported rivalry, before praising Jolie's film, Unbroken. "I mean, that movie is so beautiful and wonderful and she did such a gorgeous job. I think that it's time people stop with that petty B.S. and just start celebrating great work and stop with the petty kind of silliness."

"It's just tiresome and old," she added. "It's like an old leather shoe. Let's buy a new pair of shiny shoes."

Pitt and Aniston both moved on from their divorce and married again. Pitt married Jolie in 2014, and Aniston married actor Justin Theroux in 2015, though both their respective marriages again ended in divorce -- Jolie filed for divorce from Pitt in September 2016, and Aniston and Theroux announced their separation in February 2018. And it appears Pitt and Aniston had the same interests since becoming single again, particularly, sculpture. In March 2017, a source told ET Pitt had taken up sculpting as a hobby under the direction of his friend, British artist Thomas Houseago, spending up to 15 hours a day in the studio, until the early hours of the morning.

Last August, Aniston talked to InStyle about her love of sculpting. 

"Twelve years ago, I had a beautiful art studio, and that was my dream then," Aniston said. "I still want to take the time to have those moments for myself. I had a wheel, and I had a bunch of clay."

In February 2018, a source told ET that Pitt and Jolie have in fact remained "friendly" since their split, though they were "absolutely not" dating again.

"They have each other’s cell phone numbers and communicate from time to time," the source said. "This is nothing new. Jen and him [Brad] have remained friendly."

The source added of Pitt's love life, "He's been on casual dates, but none of them have evolved into anything serious. His dating life is certainly not his top priority. The kids are."

Meanwhile, that same month, a source told ET that dating also wasn't Aniston's priority following her split from 48-year-old Theroux.

"She won't fall in love anytime soon," a source told ET. "All her friends are around her. That is the best supportive group."

Clearly, Aniston is also great at being friends with her exes. She's remained on good terms with Theroux following their breakup last year, and last February, she once again made headlines for her relationship with Pitt when he attended her star-studded 50th birthday party at the Sunset Tower in Los Angeles. A source told ET at the time that Pitt "wanted to support" Aniston because the former couple have "been friendly" in the years following their split. According to the source, Aniston put Pitt on her invite list weeks before the party and Pitt was in town and happily chose to attend to help her celebrate the milestone birthday.

"Jen and Brad have remained friends and have spoken with each other quite a few times since they both became single," the source said. "They are friends and have supported each other through some tough times. They've come so far since their marriage and plan to stay friends for life."

"There are truly no hard feelings between them... They both realize that anytime they cross paths, people talk about a reunion," the source added. "He came on his own and quietly entered the party. They had heavy security, kept a ban on social media, and hoped for the best."

Last May, Pitt laughed off a paparazzo who asked if he and Aniston were getting back together.

"Oh, my God," he responded.

Later that year, in August, a source told ET that Aniston was starting to date again with the encouragement of her friends, including Courteney Cox and Lisa Kudrow. The source also said she and Pitt were still in touch.

"She continues to stay in touch with Brad and they occasionally talk," the source said. "They both have come so far."

Most recently, an eyewitness told ET that Pitt was one of 50 guests at Aniston's holiday party at her home on Dec. 14.

"Brad Pitt arrived at Jennifer Aniston’s holiday party a little after 7 p.m. on Saturday," the eyewitness said. "He was among the first to arrive and the second-to-last guest to leave around 11 p.m. He was dressed casually in a dark bomber jacket with a cap on. He arrived with his longtime security guard, who waited for him with his car and saw him out."

"It was very festive," the source added of the gathering. "It was a pretty low-key, casual affair. Just a gathering of close friends to celebrate the holidays."

For more of our interview with Pitt at the Golden Globes, watch the video below: