Did Jennifer Aniston Warn Angelina Jolie About Brad Pitt? Inside Their Unlikely Encounter

An alleged affair turned tumultuous relationship turned lengthy breakup, Brangelina is officially over. With the news that the couple's eight-year divorce proceedings have finally come to a close, we're looking back on the era of Brad Pitt and Angelina Jolie, starting with the illicit beginnings of their relationship. At the time of their meeting on the set of 2004's "Mr. and Mrs. Smith," Pitt was married to "Friends" sweetheart Jennifer Aniston. Her first encounter with Jolie was also her last (so far), but her words have a tinge of irony now that we know how this story reads.

In a 2005 cover story for Vanity Fair, Aniston described her only time meeting the "Girl, Interrupted" actor in a fleeting and cordial interaction on the Warner Brothers lot. "It was on the lot of 'Friends ' — I pulled over and introduced myself," Aniston recalled to the outlet. "I said, 'Brad is so excited about working with you. I hope you guys have a really good time.'" As it turns out, her husband was a little too excited about working with Jolie. After Aniston and Pitt called it quits in 2005, Brad quickly entered a romance with his co-star, leading to speculation that Pitt cheated on Aniston with Jolie.

Aniston's interview with the magazine could've acted as a warning for Jolie. Aniston told Vanity Fair of Pitt: "There's a sensitivity chip that's missing." Jolie now understands what she meant.

Both Angelina Jolie and her children have come out against Brad Pitt's seemingly hideous behavior. In 2023, their son Pax posted a scathing shoutout to his dad on Father's Day, writing (via Daily Mail): "You have made the lives of those closest to me a constant hell," adding, "Happy Father's Day, you f*****g awful human being." Jolie herself has also revealed the alleged abuse she and her children endured, alluding to Page Six that her "light was dimmed" during the years-long divorce battle with Pitt.

In 2025, two decades after her divorce from Pitt, Jennifer Aniston may actually have a chance for an "I told you so" moment when she and Jolie step foot on the same Oscars red carpet. Aniston has confirmed to friends that she will be in attendance at the award ceremony, and Jolie is an Academy Award winner, so there is a serious possibility for the star-studded showdown we've all been waiting for since 2005's infamous love triangle. However, now that both of Pitt's marriages are dead and buried, perhaps the animosity between Aniston and Jolie is gone too.