Jennifer Aniston and Brad Pitt secretly ‘talking again’: Intimate details of weekly trailer ‘lunch dates’… private visits to her home… and who made the first move

For a few glorious minutes in January 2020, Jennifer Aniston and Brad Pitt had the internet convinced Hollywood’s most famous breakup might have staged an improbable comeback.

The former golden couple – who divorced in 2005 after seven years together amid rumors Pitt had moved on with his Mr & Mrs Smith co-star Angelina Jolie – hadn’t been photographed together in more than a decade when they reunited backstage at the SAG Awards.

There was the warm hug. The megawatt smiles. And then Pitt reached for Aniston’s hand as she walked away, providing just enough fuel for hopeless romantics to start dreaming up a sequel.

By then, Pitt, 62, was years past his contentious 2016 split from Jolie, while Aniston, 57, had neatly filed away her 2018 divorce from actor Justin Theroux.

Now, the Daily Mail can reveal that, shortly after the reunion, the pair began quietly slipping back into each other’s orbit. 

One source said that, during their SAG reunion, ‘they both had new numbers, so they swapped and said they’d be in touch. Brad was the first one to text,’ while a second insider shared that Pitt soon started popping up on The Morning Show set at least once a week for a ‘standing lunch date’ in Aniston’s trailer.

Indeed, Aniston’s The Morning Show location proved to be something of a reunion hotspot.

Our second insider close to the Apple TV series said Pitt’s visits became a regular part of the show’s second season, giving the former husband and wife plenty of opportunities to reconnect away from prying eyes.

‘During season 2 of The Morning Show, Brad was coming to set and having lunch with Jen in her trailer. He would arrive and get dropped directly at her trailer for a private lunch just the two of them and then he would leave once filming for Jen resumed,’ the source explained.

‘Brad would come to set at least once a week. Some crew knew but had no idea who or how many. It was a standing lunch date and he stuck to it.’

And apparently, the studio lot wasn’t the only place where the former couple was catching up.

‘During this time, he was also hanging out with her at her house,’ said our first source, who also backed up those private rendezvous, adding: ‘Jen and Brad got together a number of times. Mainly at her house. They couldn’t be seen out in public together.’

There may have been no paparazzi shots to prove it, but the pair soon gave fans something almost as good: another very public appearance together.

In September 2020, Aniston and Pitt reunited for the viral Fast Times at Ridgemont High table read, where they gamely played the flirtatious Brad Hamilton and Linda Barrett – complete with a steamy dream sequence that had fans positively riveted. 

It was a charming reminder of the chemistry that once made them one of Tinseltown’s defining couples, and the idea of a second act was irresistible.

Still, our first insider quickly poured cold water on any romantic reunion, insisting their post-SAG bond stayed squarely in friend territory. 

‘A platonic relationship grew. Nothing more,’ the source said. ‘They’d gone through so much both privately and publicly that a romantic relationship would never be on the cards.’

A third insider echoed: ‘For Brad, there was no hidden agenda or expectation of rekindling their romance. More than anything, Brad missed having her as a trusted friend.

‘He was quickly reminded of just how important Jennifer had been in his life. He genuinely enjoyed reconnecting with her, spending time together away from the spotlight and just being friends, having private lunches was just really nice.

‘She was, and continues to be, one of the few people he feels he can trust completely. They still keep in touch from time to time. Getting back together with her and talking again was one of the best decisions that he has ever made.’

Of course, the pair had been the toast of Hollywood long before this latest chapter.

Their managers set them up in 1998, after Aniston’s split from actor Tate Donovan and Pitt’s broken engagement to Gwyneth Paltrow.

They kept things under wraps for the first few months before making their highly anticipated red-carpet debut at the 1999 Emmy Awards.

By November that year they were engaged, and in July 2000 they exchanged vows in front of 200 friends, family and co-stars at a lavish Malibu wedding – with Aniston even promising to always make Pitt his ‘favorite banana milk shake.’

The bride wore a silk-and-satin beaded gown by Lawrence Steele, while the wedding came complete with 50,000 flowers, four bands and a 13-minute fireworks display.

The couple were riding high, with Pitt even joining his then-wife on-screen for the first time in the season eight Friends Thanksgiving episode.

By 2002, the pair had launched their own production company, Plan B, which quickly became much more than a vanity project, with 17 films in production, including 2004’s Troy, starring Pitt.

And by February 2004, Aniston was talking openly about the couple’s hopes of starting a family, telling The Guardian: ‘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.’

Then, just months later, the picture-perfect Hollywood marriage began to unravel.

In January 2005, days after the pair were photographed ringing in the New Year together in Anguilla, they announced their separation. Aniston filed for divorce two months later, citing irreconcilable differences.

But the split was quickly swallowed up by scandalous speculation, as rumors swirled about Pitt’s relationship with Jolie.

In her first interview after the breakup, Aniston told Vanity Fair she was ‘shocked’ by the split 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,’ she insisted.

Aniston noted that ‘problems happen’ when a couple ‘stops growing together,’ but she did not pin the ultimate breakdown of her marriage on Jolie.

Still, the public was insatiable when it came to the love-triangle gossip, and the split quickly became a full-blown obsession.

Fans were forced to pick sides, and even popular LA boutique Kitson reported that its ‘Team Aniston’ T-shirts were outselling ‘Team Jolie’ by 25 to one.

But the drama only intensified when photographs surfaced just months after the split showing Pitt and Jolie together on a beach in Africa with Jolie’s three-year-old son, Maddox.

‘The world was shocked and I was shocked,’ Aniston later said.

Then came another headline-making moment: a W magazine spread, based on an idea from Pitt, that showed the actor and Jolie posing as a 1960s-style married couple.

The shoot left Aniston wounded – and prompted her to deliver one of the most memorable lines of the entire saga.

‘There’s a sensitivity chip that’s missing,’ she said of Pitt.

Still, despite the heartbreak, Aniston refused to publicly tear down her former husband, saying she had no interest in repeating the bitterness of her own parents’ divorce.

‘I love Brad; I really love him. I will love him for the rest of my life,’ Aniston told Vanity Fair. ‘I don’t regret any of it, and I’m not going to beat myself up about it.’

And according to our first source, those feelings eventually helped pave the way for the pair’s unlikely 2020 reconnection.

‘It literally took Jen years to forgive Brad for leaving her. However, when they bumped into each other twice in 2020 at a couple of industry events, they connected again after a long and difficult rift,’ the insider said.

‘Their split was traumatic for her and she’s all about healing and forgiving.’ 

Pitt, too, later spoke about the end of their marriage, insisting that the relationship they shared had not simply disappeared.

In 2007, he told V Magazine that he and Aniston still held a close 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.

Reflecting on their breakup, 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.’

But several years later, Pitt was hit with backlash over comments about the marriage, which many fans interpreted as a dig at Aniston.

In a 2011 Parade interview, he said he had been chasing a movie about an ‘interesting life’ while not actually living one himself, adding that his marriage had ‘something to do with it’ because he was ‘pretending the marriage was something that it wasn’t.’

Fans immediately read that as a swipe at Aniston, prompting Pitt to issue a statement insisting his words had been misinterpreted.

He stressed that Aniston was ‘an incredibly giving, loving and hilarious woman who remains my friend’ and that their relationship was ‘an important relationship I value greatly.’

But in that same interview, Pitt was also gushing about Jolie, praising their family and calling her the woman he loved.

‘I’m satisfied with making true choices and finding the woman I love, Angie, and building a family that I love so much,’ he told the magazine. ‘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 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.’

The pair later married at their French estate, Château Miraval, with all six children at the ceremony. They share Maddox, 25; Pax, 22; Zahara, 21; Shiloh, 20; and twins Knox and Vivienne, 18.

But by September 2016, that fairytale was shattered, after an infamous flight from France to Los Angeles allegedly descended into a vicious row.

Jolie accused Pitt of verbally and physically abusing her and some of the children, allegations he denied. Although the FBI and child welfare authorities investigated, no criminal charges were filed.

What followed was an eight-year custody and property war that dragged through the courts until the former couple finally reached a divorce settlement in December 2024.

By then, several of the children had already begun dropping Pitt from their names, signaling just how badly the family rift had frayed.

But in 2020, Pitt and Aniston were turning heads at the SAG Awards, both technically single and seemingly well past the old fallout.

That, of course, was before Pitt fell for jewelry executive Ines de Ramon, 33, with the pair sparking dating rumors in late 2022 before moving in together and making their red-carpet debut together at the Venice Film Festival in 2024. 

And, according to our first source, Pitt was candid with his old pal about his new love: ‘Brad told Jen after a few months of dating her he knew it was the real thing. Jen was happy for him.’

But the new relationship apparently changed the dynamic between the former spouses.

‘They both decided not to hang out anymore,’ the insider added.

Aniston, meanwhile, eventually found a new romance of her own with hypnotherapist and wellness expert Jim Curtis, 50.

The pair first sparked romance rumors in mid-2025 before going Instagram official later that year, marking Aniston’s first public relationship since her 2018 divorce from Theroux.

Still, Pitt and Aniston haven’t disappeared completely from each other’s lives.

‘They still text from time to time but that’s where their relationship stands. She likes that they’ve made peace,’ our first source said.

The Daily Mail has contacted representatives for Aniston and Pitt for comment.