October will mark twenty years since Jennifer Aniston’s divorce from Brad Pitt – a seismic event in Hollywood that, to this day, remains one of the biggest celebrity break-ups of all time. 

And, much like she did the first time around when she posed for a ‘revenge’ shoot in hot pants and a buttoned down white shirt while bashing Brad for missing a ‘sensitivity chip’, everyone’s favourite girl-next-door is back on the cover of Vanity Fair magazine – posing in gorgeous dresses and skimpy swimwear as she’s proves that, at 56, she’s just as sizzling as ever. 

She also proved that she’s still just as happy to tell her side of the story about her 2005 divorce and speak her truth about what really went down between her, Brad and ‘the other woman’, Angelina Jolie. 

But what really kept fans guessing was Jennifer’s teasing that she and Brad’s other famous ex, Gwyneth Paltrow – who dated him for three years just before Jen – still gossip about their mutual lover. 

When asked whether they ever discuss Brad together, Jen replied, ‘Oh, of course. How can we not? We’re girls.’ 

The A-list pair have been friends for years after first meeting through Jennifer’s close pal and Friends co-star, David Schwimmer, when he and Gwyneth starred alongside each other in The Pallbearer in 1997 – the year Gwyneth she split from Brad. 

Now a source tells Closer all of the details of Jennifer’s intimate chats with Gwyneth. 

The insider says, ‘Gwyneth and Jen go back a long way, they share the same publicist and have a lot of mutual friends, so there’s always plenty of common ground and banter when they get together – including their mutual ex, Brad. 

‘They’re not trying to be mean but find the comparisons quite humorous. They love putting the world to rights and having a cheeky bitch about plenty of other Hollywood people they both know, but this is the topic that makes them laugh the hardest and it’s been going on for years

‘They’ve found that through humour and telling each other relatable anecdotes it’s been a great leveler – especially after a martini or when the wine is flowing over dinner.’ 

Jennifer, who is currently dating hypnotist and author Jim Curtis – who she was seen sharing a date night with in Malibu last week – got surprisingly candid during her interview, even directly referring to Brad’s alleged affair with Angelina as the ‘love triangle’. 

Meanwhile, Gwyneth, 52 – who has been married to Brad Falchuk since 2018 – hasn’t held back on dishing all the dirt on Brad, 61, who she was also engaged to for a brief period leading up to their 1997 split. 

Appearing on the ‘Call Her Daddy’ podcast in 2023, she described sex with Brad as ‘the major chemistry, love of our life kind of…at the time’, before comparing him to Ben Affleck, who she said was ‘technically excellent’. 

And now the source says that while Jennifer is a little more coy publicly, she’s happy to swap stories with Gwyneth. 

They tell us, ‘Jen will joke about Brad’s nudist tendencies while they were together at home alone and how he would leave piles of clothes on the floor and was generally sloppy, and Gwyn will throw something in [Gwyneth and Brad famously spent a trip to St Barts completely nude when they were first dating].

‘And of course they talk about Brad’s bedroom abilities. As far as Gwyneth is concerned, Brad wasn’t anything like the lover Ben [Affleck] was and Jen usually has something to say in that area, too.

‘They’re still bitching about Brad to this day and seem to look forward to these gossip sessions. Of course they swap lots of wellness tips, but their mutual past with Brad has also been a unique bonding experience’

Someone who isn’t so happy about their gossip sessions, however, is Brad, who the source says has heard from mutual friends and thinks their dwelling on the past is ‘immature’. 

Following his split from Angelina in 2016, Brad has since moved on with jewellery designer Ines de Ramon, 32, who he began dating in 2022. 

Now the insider says, ‘It’s gotten back to Brad who finds it petty and immature. He wishes they’d find something else to talk about and if they can’t say anything nice, then don’t say it at all.’

But Gwyneth and Jennifer aren’t likely to be deterred, with both having experienced heartbreak following their mutual break ups with the star. Last month a new biography by author Amy Odell alleged how, during a private conversation in a business meeting with Aerin Lauder, the heiress to the Estée Lauder company, which took place after their split, Gwyneth had described Brad as ‘dumber than a sack of s**t’.

She is also said to have felt ‘sad’ about how swiftly Brad moved on with Jennifer.

But the source says that that didn’t stop Gwyneth from reaching out to Jennifer during the furore that surrounded Brad’s ‘affair’ with Angelina. Within nine months of Jennifer’s official divorce date from Brad, the actor and Angelina posed for a magazine photo shoot with their newborn daughter, Shiloh. It was later heartbreakingly revealed that Jennifer and Brad had been experiencing fertility struggles.

At the time, Jennifer admitted, ‘There’s a sensitivity chip that’s missing,’ adding, ‘He makes his choices. He can do—whatever. We’re divorced, and you can see why.’

Now the insider says that Gwyneth was happy to be a shoulder for Jennifer to lean on, telling us, ‘Gwyneth was very comforting towards Jen when she first got divorced and it just grew from there.’

They add, ‘Jen’s at peace with Brad now but she stands behind that quote she gave about him lacking a sensitivity chip, and Gwyneth totally agrees. They’ve shared many stories where he’d go ahead saying or doing things that were totally inappropriate or insensitive, which upset them enormously at the time, but now they see in hindsight he was just being a little dense.’

However, when the wine is flowing, the source says the two gal pals are happy to give themselves just a little pat on the bag for having dated the ‘world’s sexiest man’. 
‘At the same time, they do have a shared sense of pride that they both got to date a guy who’s undisputedly one of if not THE sexiest guys on the entire planet,’ the insider jokes.

‘So this is their way of reliving that glorious achievement and basking in it all these years later – plus enjoy a good laugh at his expense!’