Brad Pitt's exes Jennifer Aniston and Angelina Jolie could face off at Oscars after years of tension

Brad Pitt's exes Jennifer Aniston and Angelina Jolie could face off at Oscars after years of tension
The tension between Jennifer Aniston and Angelina Jolie dates back to 2004 when rumors swirled that her romance with Brad Pitt began while he was still married to Aniston (Steve Granitz/FilmMagic, Daniele Venturelli/Getty Images)

LOS ANGELES, CALIFORNIA: Hollywood is bracing for a potentially dramatic moment as Jennifer Aniston and Angelina Jolie are set to attend the upcoming Oscars in March, marking what could be their first public encounter in years.

The two actresses, who share a complicated history involving Brad Pitt, may cross paths on the red carpet, reigniting speculation about their enduring animosity.

Jennifer Aniston and Angelina Jolie poised for Oscars face-off after years of tension

Jennifer Aniston attends the 76th Primetime Emmy Awards at Peacock Theater on September 15, 2024 in Los Angeles, California. (Photo by Frazer Harrison/Getty Images)
Jennifer Aniston attends the 76th Primetime Emmy Awards at Peacock Theater on September 15, 2024 in Los Angeles, California (Frazer Harrison/Getty Images)

Sources close to Aniston, 55, reveal that while she is a regular at the Oscars, the prospect of facing Jolie, 49, is causing her significant anxiety. Jolie is widely expected to earn a Best Actress nomination for her role in 'Maria', a Netflix production.

"Hollywood is a very small town," a source shared, "and with Angelina in the running for an Oscar, it’s going to take a big effort from Jen to avoid her in the coming months."


NEW YORK, NEW YORK - JUNE 16: Angelina Jolie attends the 77th Annual Tony Awards at David H. Koch Theater at Lincoln Center on June 16, 2024 in New York City. (Photo by Jamie McCarthy/WireImage)
Angelina Jolie attends the 77th Annual Tony Awards at David H. Koch Theater at Lincoln Center on June 16, 2024 in New York City (Jamie McCarthy/WireImage)

The source continued, "On top of that, Jen feels Ange is starting to encroach on some of her professional relationships, too. She produced 'Maria' with Netflix, who Jen has worked with extensively in the past. Jen has been a huge force in show business in recent years, but now Angelina is back up there with her. But Jen is determined to be at the Oscars event."

Jennifer Aniston and Angelina Jolie’s longstanding tension

LOS ANGELES - SEPTEMBER 19: Actors Jennifer Aniston and husband Brad Pitt attend the 56th Annual Primetime Emmy Awards at the Shrine Auditorium September 19, 2004 in Los Angeles, California. (Photo by Kevin Winter/Getty Images)
Actors Jennifer Aniston and husband Brad Pitt attend the 56th Annual Primetime Emmy Awards at the Shrine Auditorium September 19, 2004 in Los Angeles, California (Kevin Winter/Getty Images)

The tension between Aniston and Jolie dates back to 2004 when rumors swirled that Jolie’s romance with Pitt began while he was still married to Aniston. Although Pitt and Jolie ended their relationship in 2016, Aniston has reportedly struggled to move past the betrayal.

An insider noted, "The amount of animosity between them was ridiculous. Jen holds Ange responsible for her and Brad’s break-up. She sees her as a 'home-wrecker.' Jen feels Angelina was very arrogant about the situation and she feels her relationship with Brad helped solidify this narrative in people’s minds that Jen was too career-driven to give him children."

NEW YORK, NY - NOVEMBER 04: 2015 Entertainment Innovator Angelina Jolie Pitt (L) and Brad Pitt atten
 Angelina Jolie Pitt and Brad Pitt attend the WSJ. Magazine 2015 Innovator Awards at the Museum of Modern Art on November 4, 2015 in New York City (Dimitrios Kambouris/Getty Images for WSJ. Magazine 2015 Innovator Awards)

"If Jen had moved on, and found lasting love again and had kids of her own, she probably would be able to let it go," the insider explained. "But that hasn’t happened and she holds Angelina responsible for a whole lot of pain in her life."

Despite Aniston remaining single since her 2018 split from her second husband, Justin Theroux, and while Aniston and Pitt have reconciled in recent years, the same cannot be said for Aniston and Jolie.

"Jen can’t stand to look at her, and she avoids her wherever possible. For a long time, she felt the same about Brad, but he reached out to make amends a while ago, so she was able to forgive him," the source said.

They added, "If Angelina had ever tried to get in touch and talk things over, Jen likely would have been able to let this go, but it hasn’t even come close to that, and isn’t likely to. Angelina feels that she did nothing wrong and so, therefore, has nothing to apologize for."

Brad Pitt and Angelina Jolie's divorce settlement after 8-year battle

Writer-director-producer-actress Angelina Jolie Pitt (L) and actor-producer Brad Pitt attend Audi at the opening night gala premiere of 'By the Sea' during AFI FEST 2015 presented by Audi at TCL Chinese 6 Theatres on November 5, 2015, in Hollywood, California (Photo by Jonathan Leibson/Getty Images for Audi)
Angelina Jolie Pitt (L) and actor-producer Brad Pitt attend Audi at the opening night gala premiere of 'By the Sea' during AFI FEST 2015 presented by Audi at TCL Chinese 6 Theatres on November 5, 2015, in Hollywood, California (Jonathan Leibson/Getty Images for Audi)

After nearly a decade of legal disputes, Brad Pitt and Angelina Jolie have reached a settlement in their divorce proceedings.

Jolie, 49, filed for divorce in 2016, just two years after her marriage to Pitt, 61.

Her lawyer, James Simon, reflected on the journey, stating, "This is just one part of a long ongoing process that started eight years ago. Frankly, Angelina is exhausted, but she is relieved this one part is over."

Jolie, who has focused on creating a peaceful and healing environment for her family, reportedly does not speak negatively about Pitt, either publicly or privately. "She’s been trying hard to be light after a dark time," a source shared.

The settlement comes as part of a private agreement between the former couple, who are parents to six children: Maddox, 23, Pax, 21, Zahara, 19, Shiloh, 18, and 16-year-old twins Knox and Vivienne. Jolie initiated the divorce after an alleged violent incident aboard a private plane in 2016 involving Pitt and the children.

Court documents regarding the settlement are pending, and a judge's approval will finalize the agreement.

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