Brad Pitt and Jennifer Aniston secretly resumed their friendship following the 2020 SAG Awards. Pitt began visiting Aniston for a weekly standing lunch date on the set of the Apple TV series The Morning Show.
According to an insider, Pitt was dropped off directly at Aniston's trailer for a private lunch during filming for the second season of the show. The 62-year-old actor would leave when 57-year-old Aniston resumed filming.
A source said Pitt and Aniston exchanged new phone numbers at the SAG Awards and promised to stay in touch. "Brad was the first one to text," the source said.
Another insider said some crew members knew about the regular lunch dates but did not know who was visiting. The source said Pitt stuck to the weekly arrangement.
The former married couple also spent time at Aniston's home. A source said they got together several times in private because they could not be seen in public together.
Platonic friendship
Insiders said the reconnection was entirely platonic. One source said a romantic relationship was never a possibility because they had gone through so much publicly and privately.
A third insider said Pitt had no hidden agenda to rekindle a romance. The source said Pitt genuinely enjoyed reconnecting and spending time away from the spotlight.
"More than anything, Brad missed having her as a trusted friend," the source said. The insider said Aniston remains one of the few people Pitt feels he can completely trust.
Getting back in touch was one of the best decisions Pitt ever made, according to the source. The pair also reunited publicly in September 2020 for a Fast Times at Ridgemont High table read, playing Brad Hamilton and Linda Barrett.
Their managers originally set them up in 1998. Aniston had recently split from actor Tate Donovan, and Pitt had ended his engagement to Gwyneth Paltrow.
They made their red carpet debut at the 1999 Emmy Awards and were engaged by November of that year.
Marriage and separation
Pitt and Aniston married in July 2000 at a Malibu wedding with 200 friends, family members and co-stars. The event featured four bands, 50,000 flowers and a 13-minute fireworks display. Aniston wore a Lawrence Steele silk-and-satin beaded gown and promised to make Pitt his favorite banana milkshake.
Pitt appeared on screen with Aniston during the season eight Thanksgiving episode of Friends. In 2002, the couple launched Plan B, a production company that developed 17 films, including the 2004 film Troy, which starred Pitt.
Aniston told The Guardian in February 2004 that the couple hoped to start a family. "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 said.
The couple announced their separation in January 2005, days after being photographed celebrating the New Year in Anguilla. Aniston filed for divorce two months later, citing irreconcilable differences.
Divorce aftermath
Rumors circulated regarding Pitt and his Mr & Mrs Smith co-star Angelina Jolie. In her first post-breakup interview with Vanity Fair, Aniston said she was shocked and trying to pick up the pieces.
"Am I lonely? Yes. Am I upset? Yes. Am I confused? Yes. Do I have my days when I've thrown a little pity party for myself? Absolutely. But I'm also doing really well," Aniston said.
Aniston said problems happen when a couple stops growing together, but she did not blame Jolie for the end of her marriage. Fans took sides, with the Los Angeles boutique Kitson reporting that its Team Aniston shirts outsold Team Jolie shirts by 25 to one.
Photographs later surfaced showing Pitt on an African beach with Jolie and her three-year-old son Maddox.
"The world was shocked and I was shocked," Aniston later said.
Pitt then proposed a W magazine photo shoot featuring himself and Jolie as a married couple in the 1960s. Aniston responded by saying of Pitt, "There's a sensitivity chip that's missing."
Healing and forgiving
Aniston told Vanity Fair she did not want to repeat the bitterness of her parents' divorce. "I love Brad; I really love him. I will love him for the rest of my life," she said. "I don't regret any of it, and I'm not going to beat myself up about it."
A source said it took Aniston years to forgive Pitt for leaving her, calling the split traumatic. The insider said Aniston focuses on healing and forgiving, which helped them reconnect when they bumped into each other twice at 2020 industry events.
Pitt told V Magazine in 2007 that he and Aniston maintained a deep friendship. "Jen and I still maintain a deep friendship and have a lot of life together that isn't erased in any way," he said.
"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," Pitt said.
Later relationships
In a 2011 Parade interview, Pitt said he had been chasing a movie about an interesting life while not living one himself. He said his marriage had something to do with it because he was "pretending the marriage was something that it wasn't."
Following public backlash, Pitt released a statement saying his words were misinterpreted. He called Aniston "an incredibly giving, loving and hilarious woman who remains my friend" and described their connection as an important relationship he valued greatly.
In the same Parade interview, Pitt praised Jolie. "I'm satisfied with making true choices and finding the woman I love, Angie, and building a family that I love so much," he said.
"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," Pitt told the magazine. He added, "One of the greatest, smartest things I ever did was give my kids Angie as their mom. She is such a great mom. Oh, man, I'm so happy to have her."
Pitt and Jolie married at Château Miraval in France. They share six children, Maddox, 25, Pax, 22, Zahara, 21, Shiloh, 20, and twins Knox and Vivienne, 18.
They separated in September 2016 following an alleged altercation on a flight from France to Los Angeles. Jolie accused Pitt of physically and verbally abusing her and some of the children. Pitt denied the allegations, and the FBI and child welfare authorities filed no criminal charges.
Moving on
A custody and property dispute lasted eight years until the former couple reached a divorce settlement in December 2024. Several of the children have dropped Pitt from their names.
Pitt began dating 33-year-old jewelry executive Ines de Ramon in late 2022. They moved in together and made their red-carpet debut at the 2024 Venice Film Festival.
A source said Pitt told Aniston about de Ramon after a few months of dating, saying he knew the relationship was real. The source said Aniston was happy for him, but they decided to stop hanging out.
Aniston began dating hypnotherapist and wellness expert Jim Curtis, 50, in mid-2025. They made the relationship official on Instagram later that year. It was Aniston's first public relationship since she divorced actor Justin Theroux in 2018.
A source said Pitt and Aniston still text occasionally and that Aniston is glad they made peace. The Daily Mail contacted representatives for both actors for comment.
